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Journal articles on the topic 'Cyclohexanedione-1,3(Methyl-2 Oxo-3p Butyl-2)|Ent'

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Published: 14 July 2021

Last updated: 17 February 2022

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1

Liepa, AJ, AJ Liepa, JS Wilkie, et al. "Preparation of Bicyclic Herbicide Precursors by Intramolecular Stork-Danheiser Kinetic Alkylation Reactions of Methyl 1-(Haloalkyl)-3-methoxy-5-oxocyclohex-3-ene-1-carboxylate Derivatives." Australian Journal of Chemistry 45, no. 4 (1992): 759. http://dx.doi.org/10.1071/ch9920759.

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Reductive alkylation of methyl 3,5-dimethoxybenzoate with the dibromoalkane and the bromochloroalkane derivatives (4a-d) and (4e-g) afforded, after acid hydrolysis, the corresponding methyl 1-( haloalkyl )-3-methoxy-5-oxocyclohex-3-ene-1-carboxylate derivatives (6a-g). Reaction of (6a-c) with lithium diisopropylamide afforded methyl 3-methoxy-5-oxobicyclo[4.2.0]oct-3-ene- 1-carboxylate (2a), methyl 5-methoxy-7-oxo-1,2,3,4,7,7a-hexahydro-3aH-indene-3a-carboxylate (2b) and methyl 6-methoxy-8-oxo-1,3,4,5,8,8a-hexahydronaphtha1ene-4a(2 H)- carboxylate (2c), respectively. Compounds (2b) and (2c) we

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2

Alexander, Mariano S., Henry North, Kenneth R. Scott, and Ray J. Butcher. "tert-Butyl 6-methyl-2-oxo-4-[4-(trifluoromethoxy)anilino]cyclohex-3-ene-1-carboxylate." Acta Crystallographica Section E Structure Reports Online 66, no. 12 (2010): o3229. http://dx.doi.org/10.1107/s1600536810046969.

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3

Klinot, Jiří, Jarmil Světlý, Eva Klinotová, Miloš Buděšínský та Alois Vystrčil. "Preparation of isomeric 2-methyl-1-oxotriterpenoids of the 18α-oleanane series; Conformation of ring A". Collection of Czechoslovak Chemical Communications 51, № 12 (1986): 2869–78. http://dx.doi.org/10.1135/cccc19862869.

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2β-Methyl-1α-hydroxy (XV) and two isomeric 2-methyl-1-oxo derivatives (XVI and XVII) of 19β,28-epoxy-18α-oleanane were prepared from 19β,28-epoxy-2-methyl-18α-olean-1-en-3-one (XI) via 3β-chloro derivative XIII and unsaturated 1α-hydroxy derivative XIV. Allylic oxidation of 2-methyl-2-ene VI was studied as an alternative approach to compound XIV. Oxidation with selenium dioxide led to diol VII, aldehyde VIII and alcohol IV, oxidation with tert-butyl chromate gave epoxy ketone X. According to 1H NMR and CD data, ring A in the 2β-methyl derivatives XV and XVI exists in a boat conformation. The 2

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4

Yates, Peter, Rupinder S. Grewal, Peter C. Hayes, and Jeffery F. Sawyer. "Synthesis of cedranoid sesquiterpenes. V. The biotols." Canadian Journal of Chemistry 66, no. 11 (1988): 2805–15. http://dx.doi.org/10.1139/v88-434.

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Reduction of dimethyl 3-hydroxy-4,4,8-trimethyl-6-oxo-cis-bicyclo[3.3.0]octa-2,7-diene-1,2-dicarboxylate (8) with lithium and ammonia gives dimethyl 3-hydroxy-4,4,exo-8-trimethyl-6-oxo-cis-bicyclo[3.3.0]oct-2-ene-1,2-dicarboxylate (9), which on acetylation, reduction with sodium borohydride, and methanolysis gives dimethyl 3,exo-6-dihydroxy-4,4,exo-8-trimethyl-cis-bicyclo[3.3.0]oct-2-ene-1,2-dicarboxylate (12). This on 2-decarbomethoxylation followed by treatment with lithium acetylide in the presence of cerium trichloride gives methyl 3-ethynyl-3,exo-6-dihydroxy-4,4,exo-8-trimethyl-cis-bicycl

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5

Mamaghani, Manouchehr, and Alireza Alizadehnia. "Enzyme Catalysed Kinetic Resolution of Racemic Methyl 3-acethylbicyclo [2.2.1] hept-5-ene-2-carboxylate using pig's liver esterase†." Journal of Chemical Research 2002, no. 8 (2002): 386–87. http://dx.doi.org/10.3184/030823402103172400.

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Racemic methyl 3- endo-acetylbicyclo[2.2.1]hept-5-ene-2- exo-carboxylate and methyl 3- exo-acetylbicyclo[2.2.1]hept-5-ene-2- endo-carboxylate were prepared (as a 1:1 mixture in 98% yield) from (E)-methyl 4- oxo-2-pentenoate, using Diels–Alder methodology. The mixture was separated chromatographically and resolved into the enantiomers by pig liver esterase (PLE) with low to high ee's (98%).

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6

Yao, Li-Ying, Chen Zhang, and Bi-Song Wang. "(R,S)-Methyl 3-methyl-5-oxo-1-phenylcyclohex-3-ene-1-carboxylate." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (2006): o2768—o2769. http://dx.doi.org/10.1107/s1600536806021441.

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The title compound, C15H16O3, has two molecules in the asymmetric unit. The cyclohex-2-enone ring has an envelope conformation in both molecules. The crystal exhibits twinning. The molecular packing in the crystal structure is determined by weak intermolecular C—H...O interactions.

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7

ARORA, A. K., J. SINGH, M. SHARMA, and G. L. KAD. "ChemInform Abstract: Synthesis of 2-Methyl-6-(4-tolyl)hept-1-ene (III), 2-Methyl-6-(2-oxo-4- methylcyclohex-3-en-1-yl)-1-heptanol (VII) and 2-Methyl-6-(2-oxo-4- methylcyclohex-3-en-1-yl)-1-heptanal (VIII)." ChemInform 27, no. 34 (2010): no. http://dx.doi.org/10.1002/chin.199634251.

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8

Nokami, Junzo, Kazuhiko Fujii, Yusuke Mizutani, et al. "Cyclopentanoids from Cyclopentadiene: Synthesis of (-)-Methyl jasmonate and (+)-12-Oxophytodienoic acid." Natural Product Communications 8, no. 7 (2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800716.

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Linoleic acid metabolites (-)-methyl jasmonate and (+)-12-oxophytodienoic acid ((+)-12-oxo-PDA) were prepared from the same precursor (1,2-trans, 1,3- cis, 2′ Z)-2-(pent-2′-enyl)-cyclopent-4-en-1,3-diol which was obtained by regioselective pent-2-enylation of cyclopentadiene and following photooxidation to cis −1,3-diol. A methoxycarbonylmethyl substituent was introduced to the cyclopentane ring via alkylation of the π-allyl palladium intermediate derived from (1 R,2 S,3 S,2′ Z)-3-acetoxy-2-(pent-2′-enyl)cyclopent-4-ene-1-ol with dimethyl malonate for (-)-methyl jasmonate. The α-chain was intr

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9

Yates, Peter, D. Jean Burnell, Vernon J. Freer, and Jeffery F. Sawyer. "Synthesis of cedranoid sesquiterpenes. III. Functionalization at carbon 4." Canadian Journal of Chemistry 65, no. 1 (1987): 69–77. http://dx.doi.org/10.1139/v87-012.

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Dimethyl 6,6-dimethyl-5,7-dioxobicyclo[2.2.2]oct-2-ene-2,3-dicarboxylate (8) on irradiation in acetophenone gives dimethyl 6,6-dimethyl-4,7-dioxotricyclo[3.2.1.02,8]octane-1,8-dicarboxylate (13), which on treatment with lithium dimethylcuprate followed by monodecarbomethoxylation gives methyl 4,4-endo-8-trimethyl-3,6-dioxo-cis-bicyclo[3.3.0]octane-1-carboxylate (17). Similar irradiation of dimethyl 4,6,6-trimethyl-5,7-dioxobicyclo[2.2.2]oct-2-ene-2,3-dicarboxylate (24) and its 7,7-ethylenedioxy derivative (25) followed by treatment with DBU and concentrated H2SO4, respectively, gives dimethyl

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10

Bartolucci, Gianluca, Bruno Bruni, Massimo Di Vaira, and Valerio Giannellini. "2-Butyl-4-oxo-3-{[2′-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-3-aza-1-azoniaspiro[4.4]non-1-ene chloride 1.69-hydrate (irbesartan hydrochloride 1.69-hydrate)." Acta Crystallographica Section E Structure Reports Online 63, no. 4 (2007): o1529—o1531. http://dx.doi.org/10.1107/s1600536807008951.

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11

Aragao, Valquiria, Mauricio Constantino, Adilson Beatriz, and Gil José da Silva. "Synthesis of 1-Methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic Acid Methyl Ester." Molecules 10, no. 11 (2005): 1413–18. http://dx.doi.org/10.3390/10111413.

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12

Ogbuchiekwe, Edmund J., Milton E. McGiffen, Joe Nunez, and Steven A. Fennimore. "Tolerance of Carrot to Low-rate Preemergent and Postemergent Herbicides." HortScience 39, no. 2 (2004): 291–96. http://dx.doi.org/10.21273/hortsci.39.2.291.

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Preemergent and postemergent herbicides were evaluated in the Mediterranean climate of the southern San Joaquin Valley and the desert climate of the Imperial Valley from 1998 through 2000. Sixteen herbicide treatments were applied both as preemergence (PRE) and postemergence (POST) applications to carrot (Daucus carota L.). Carrot was generally more tolerant to PRE herbicide applications than to POST applications. Carrot was tolerant to PRE and POST imazamox and triflusulfuron at both locations. Carrot root losses due to herbicide were consistent with visual ratings. Treatments that injured ca

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13

Sharif, Shahzad, Mehmet Akkurt, Islam Ullah Khan, Manan Ayub Salariya, and Sarfraz Ahmad. "7-Benzenesulfonamido-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]octa-2-ene-2-carboxylic acid monohydrate." Acta Crystallographica Section E Structure Reports Online 66, no. 1 (2009): o73—o74. http://dx.doi.org/10.1107/s1600536809051769.

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14

Fischer, Andreas, H. S. Yathirajan, B. V. Ashalatha, B. Narayana, and B. K. Sarojini. "Ethyl 4-(3-bromo-2-thienyl)-2-oxo-6-phenylcyclohex-3-ene-1-carboxylate." Acta Crystallographica Section E Structure Reports Online 64, no. 3 (2008): o560. http://dx.doi.org/10.1107/s1600536808002717.

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15

Haba, Hamada, Laurence Marcourt, Mohammed Benkhaled, and Christophe Long. "Minor Ent-abietane Diterpenoids from Euphorbia guyoniana." Natural Product Communications 8, no. 11 (2013): 1934578X1300801. http://dx.doi.org/10.1177/1934578x1300801105.

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Three new abietane-type diterpenoids: ent-abieta-8,11,13-trien-16-ol (1), ent-abieta-8,11,13-trien-11,16-diol (2) and 11,12-dihydroxy-7-oxo- ent-abieta-8,11,13-trien-16-oic acid methyl ester (3), in addition to three known triterpenoids: euphol (4), 24,25-epoxycycloartanol (5) and β-sitosterol O-β-D-glucoside (6) were isolated from the chloroform extract of the roots of Euphorbia guyoniana. Structures of the isolated compounds were established on the basis of spectroscopic analyses, including 1D and 2D homo and heteronuclear NMR experiments and ESIMS, and comparison with literature data.

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16

Hakimelahi, Gholam H., and Ali A. Jarrahpour. "Synthesis of ethylcis 2-[(Diethoxyphosphoryl)methyl]-7-oxo-3-phenyl-6-phthalimido-l-azabicyclo[3.2.0]hept-3-ene-2-carboxylate and Methylcis-2-Bromo-3-methyl-8-oxo-7-phthalimido-4-oxa-1-azabicyclo[4.2.0]octane-2-carboxylate." Helvetica Chimica Acta 72, no. 7 (1989): 1501–5. http://dx.doi.org/10.1002/hlca.19890720711.

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17

Fischer, Andreas, M. T. Swamy, B. Narayana, and H. S. Yathirajan. "rac-Ethyl 3-(3-bromo-2-thienyl)-2-oxo-6-(4-propoxyphenyl)cyclohex-3-ene-1-carboxylate." Acta Crystallographica Section E Structure Reports Online 64, no. 11 (2008): o2152. http://dx.doi.org/10.1107/s1600536808032650.

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18

Manguro, Lawrence Onyango Arot, Sylvia Awino Opiyo, Eberhardt Herdtweck, and Peter Lemmen. "Triterpenes of Commiphora holtziana oleo-gum resin." Canadian Journal of Chemistry 87, no. 8 (2009): 1173–79. http://dx.doi.org/10.1139/v09-078.

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Chemical analysis of the acetone extract of Commiphora holtziana gum resin has led to the isolation of triterpenes characterized as methyl 3-oxo-1α,19α,28-trihydroxyurs-12-en-24-oate (1), methyl 3β-acetyl-2α,11α,19α,28-tetrahydroxyurs-12-en-24-oate (2), methyl 3β,11α-diacetyl-1α,2α,28-trihydroxyurs-12-ene-24-oate (3), and 3β,28-diacetyl-1α,2α,25-trihydroxydammar-23-ene (4). The known compounds isolated from the same extract included cabraleadiol monoacetate (5), mansumbinol (6), 3β-acetylamyrin (7), 3α-acetylboswellic acid (8), 2-methoxy-8,12-epoxygermacra-1(10),7,11-trien-6-one (9), 2-methoxy

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19

Li, Hongqi, Anil N. Mayekar, B. Narayana, H. S. Yathirajan, and W. T. A. Harrison. "Ethyl 6-(6-methoxy-2-naphthyl)-2-oxo-4-(2-thienyl)cyclohex-3-ene-1-carboxylate." Acta Crystallographica Section E Structure Reports Online 65, no. 7 (2009): o1533. http://dx.doi.org/10.1107/s1600536809021308.

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20

Anuradha, N., A. Thiruvalluvar, K. Pandiarajan, and C. Yuvaraj. "Ethyl 6-r-(2-chlorophenyl)-2-oxo-4-phenylcyclohex-3-ene-1-t-carboxylate." Acta Crystallographica Section E Structure Reports Online 65, no. 1 (2008): o191. http://dx.doi.org/10.1107/s1600536808043055.

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21

Tang, Chao, Li Cai, Shuai Liu, et al. "Crystal structure of tebipenem pivoxil." Acta Crystallographica Section E Crystallographic Communications 74, no. 9 (2018): 1215–17. http://dx.doi.org/10.1107/s2056989018010770.

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The molecular structure of the first orally active carbapenem antibacterial agent, tebipenem pivoxil (systematic name: (2,2-dimethylpropanoyloxy)methyl (4R,5S,6S)-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate), C22H31N3O6S2, has been determined and the configurations of the four chiral centers validated. The title compound crystallizes in the triclinic space group P1 with one molecule in the unit cell. Three out of the four rings adopt planar conformations while the thiazolinyl ring adopts an envel

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22

Yermolayev, Sergey A., Nickolay Yu Gorobets, Oleg V. Shishkin, Svetlana V. Shishkina, and Nicholas E. Leadbeater. "Pathways for cyclizations of hydrazine-derived 2-(2-cyanovinyl)-3-oxo-cyclohex-1-ene enolates." Tetrahedron 67, no. 16 (2011): 2934–41. http://dx.doi.org/10.1016/j.tet.2011.02.052.

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23

B. Motherwell, William, Catherine S. V. Houge-Frydrych, and Dennis M. O'Shea. "Controlled Annulation Reactions of 3-Methyl-4-oxo-1-thiacyclopent-2-ene-1,1-dioxide: A Useful Isoprenoidal Synthon." HETEROCYCLES 28, no. 2 (1989): 603. http://dx.doi.org/10.3987/com-88-s69.

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24

Fun, Hoong-Kun, Samuel Robinson Jebas, Jyothi N. Rao, and B. Kalluraya. "Ethyl 4-(4-methoxyphenyl)-2-oxo-6-phenylcyclohex-3-ene-1-carboxylate." Acta Crystallographica Section E Structure Reports Online 64, no. 12 (2008): o2448. http://dx.doi.org/10.1107/s1600536808039093.

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25

Corrêa, Rodrigo S., Lucienir P. Duarte, Grácia D. F. Silva, Djalma M. de Oliveira, Javier Ellena та Antônio C. Doriguetto. "16α-Hydroxyfriedelin and 3-Oxo-16-methylfriedel-16-ene as Building Blocks: Crystal Structure and Hirshfeld Surfaces Decoding Intermolecular Contacts". Journal of Crystallography 2013 (24 жовтня 2013): 1–6. http://dx.doi.org/10.1155/2013/539163.

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In this paper the importance of C–H⋯O intermolecular hydrogen bonds and van der Waals forces in crystal packing stabilization of 16α-hydroxyfriedelin (1) and 3-oxo-16-methylfriedel-16-ene (2) is described. Compound 1 is a natural product isolated from the hexane extract of Salacia elliptica branches, whereas compound 2 is obtained from compound 1 after dehydration accompanied by methyl migration of C-17 to C-16. The single-crystal X-ray diffraction experiments for 1 and 2 were carried out at 150 K, and the crystallographic study demonstrated that these compounds crystallize in noncentrosymmetr

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26

Hřebabecký, Hubert, and Antonín Holý. "Synthesis of Carbocyclic 4'-C-Hydroxymethyl Analogues of Azidodeoxythymidine, Deoxythymidine, Deoxydidehydrothymidine and Thymidine Carba Analogue with Fused Oxetane Ring." Collection of Czechoslovak Chemical Communications 65, no. 3 (2000): 395–406. http://dx.doi.org/10.1135/cccc20000395.

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Tosylation of (±)-1-[trans-4-hydroxy-3,3-bis(hydroxymethyl)cyclopentyl]-5-methylpyrimidine-2(1H),4(3H)-dione (1) and (±)-1-[cis-4-hydroxy-3,3-bis(hydroxymethyl)cyclopentyl]-5-methylpyrimidine-2(1H),4(3H)-dione (2) and treatment of the obtained 1-{(1R*,3R*,4S*)- 4-hydroxy-3-(hydroxymethyl)-3-[(tosyloxy)methyl]cyclopentyl}-5-methylpyrimidine- 2(1H),4(3H)-dione (6) and 1-{(1R*,3S*,4R*)-4-hydroxy-3-(hydroxymethyl)-3-[(tosyloxy)- methyl]cyclopentyl}-5-methylpyrimidine-2(1H),4(3H)-dione (9) with methanolic sodium methoxide gave 1-[(1R*,4S*,6S*)-4-hydroxymethyl-2-oxabicyclo[3.2.0]hept-6-yl]-5-methylp

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27

Bateson, John H., Stephen C. M. Fell, and Robert Southgate. "Synthesis of the 3-acetoxy-7-oxo-1-azabicyclo [3.2.0] hept-2-ene-2-carboxylate system." Tetrahedron Letters 27, no. 49 (1986): 6001–4. http://dx.doi.org/10.1016/s0040-4039(00)85383-6.

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28

Novoa de Armas, Héctor, Eladio Pardillo-Fontdevila, and Ramón Pomés Hernández. "Crystal and X-ray powder diffraction data for cefotaxime sodium salt, C16H16N5NaO7S2." Powder Diffraction 14, no. 2 (1999): 142–44. http://dx.doi.org/10.1017/s0885715600010460.

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An indexed powder diffraction pattern and related crystallographic data are reported for cefotaxime sodium salt: 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-[[(2amino-4-thiazolyl)(methoxyimino)-acetyl]amino]-8-oxo, monosodium salt, [6R−[6α,7β(Z)]], C16H16N5NaO7S2. The unit cell dimensions were determined from diffractometer methods, using monochromatic CuKα1 radiation, and evaluated by indexing programs. The monoclinic cell found for cefotaxime sodium was a=13.063(2) Å, b=8.916(2) Å, c=9.726(2) Å, β=107.34(2)°, Z=2, space groups: P21 (No. 4) or P21/m (No. 11)

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29

Mohan, Billava J., Balladka K. Sarojini, Hemmige S. Yathirajan, Ravindranath Rathore, and Christopher Glidewell. "Crystal structure of ethyl (1RS,6SR)-4-(2-methyl-1H-imidazol-4-yl)-2-oxo-6-(2,3,5-trichlorophenyl)cyclohex-3-ene-1-carboxylate." Acta Crystallographica Section E Crystallographic Communications 72, no. 1 (2016): 31–34. http://dx.doi.org/10.1107/s2056989015023245.

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The title compound, C19H17Cl3N2O3, has been prepared in a cyclocondensation reaction between 2,3,5-trichlorobenzaldehye and 4-acetyl-2-methyl-1H-imidazole. The cyclohexenone ring adopts an envelope conformation with the C atom substituted by the trichlorophenyl ring as the flap. The mutuallytransester and aryl substituents both occupy equatorial sites. In the crystal, a combination of N—H...O and C—H...N hydrogen bonds links the molecules into ribbons of edge-fused centrosymmetric rings, which encloseR22(14) andR44(16) alternate ring motifs, propagating along theb-axis direction.

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30

Trehan, Inder R., Jasvinder Singh, Ajay K. Arora, Jasamrit Kaur, and Goverdhan L. Kad. "Synthesis via Ultrasound: A Convenient Synthesis of 6-(4-Tolyl)hept-1-ene and 6-(2-Oxo-4-methylcyclohex-3-en-1-yl)hept-1-ene." Collection of Czechoslovak Chemical Communications 59, no. 8 (1994): 1889–91. http://dx.doi.org/10.1135/cccc19941889.

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6-(4-Tolyl)hept-1-ene (I) and 6-(2-oxo-4-methylcyclohex-3-en-1-yl)hept-1-ene (II), monocyclic norsesquiterpenes from aerial parts of South African Senecio digitalifolius, have been synthesized using ultrasonic waves and tandem phenylation reduction.

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31

Yavari, Issa, Anvar Mirzaei, Loghman Moradi, and Ako Mokhtarporiani‐Sanandaj. "Efficient Synthesis of Trialkyl (E)‐3‐{3‐Oxo‐2‐3,4‐dihydro‐2‐(1H)‐quinoxalinylidene}‐prop‐1‐ene‐1,2,3‐tricarboxylates." Synthetic Communications 37, no. 7 (2007): 1195–200. http://dx.doi.org/10.1080/00397910701199110.

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32

Swigor, J. E., C. U. Kim, and K. A. Pittman. "Synthesis of (5R,6S)-6-[(1R)-hydroxyethyl]-3-[1-methylpyridinium-2-YL-methanethio]-[3-14C]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate." Journal of Labelled Compounds and Radiopharmaceuticals 25, no. 6 (1988): 603–8. http://dx.doi.org/10.1002/jlcr.2580250604.

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33

Fareed, Ghulam, Mahboob A. Kalhoro, Muhammad A. Versiani, Nighat Afza, and Nazia Fareed. "7-{[2-(4-Hydroxyphenyl)methylidene]amino}-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid." Molbank 2012, no. 2 (2012): M756. http://dx.doi.org/10.3390/m756.

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34

Yermolayev, Sergey A., Nickolay Yu Gorobets, Oleg V. Shishkin, Svetlana V. Shishkina, and Nicholas E. Leadbeater. "ChemInform Abstract: Pathways for Cyclizations of Hydrazine-Derived 2-(2-Cyanovinyl)-3-oxo-cyclohex-1-ene Enolates." ChemInform 42, no. 34 (2011): no. http://dx.doi.org/10.1002/chin.201134153.

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35

MARUBAYASHI, Nobuhiro, Kouichi MIZUKI, and Noriaki HIRAYAMA. "Crystal Structure of (5S,6R,7R)-(4-Methoxyphenyl)methyl 3-hydroxy-7-(2-phenylacetylamino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate 5-oxide." Analytical Sciences 15, no. 7 (1999): 717–18. http://dx.doi.org/10.2116/analsci.15.717.

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36

Kato, Y. "3-Hydroxy-2-oxo-1-oxaspiro[4.5]-dec-3-ene, a New Inhibitor of Lactate Dehydrogenase." Tetrahedron Letters 36, no. 27 (1995): 4809–12. http://dx.doi.org/10.1016/00404-0399(50)0900w-.

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37

Li, Jian-Jun, Shu-Hui Jin, Xiao-Mei Liang, De-Kai Yuan, and Dao-Quan Wang. "2-(Bromophenylimino)-10-oxo-9-oxa-1-thia-3,4-diazaspiro[4.15]eicosa-3-ene." Acta Crystallographica Section E Structure Reports Online 63, no. 4 (2007): o1940—o1941. http://dx.doi.org/10.1107/s1600536807012330.

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38

Zolotoi, A. B., S. V. Konovalikhin, P. M. Lukin, O. A. D'yachenko, S. P. Zil'berg, and O. E. Nasakin. "Chemistry of 1,1,2,2-tetracyanoethane. 11. Synthesis and stereochemical characteristics of 3-methyl-5-oxo-2?-amino-5?-phenyl -3?,4?,4?-tricyanoisoxazoline-4-spiro-1?-cyclopent-2?-ene." Chemistry of Heterocyclic Compounds 24, no. 10 (1988): 1166–71. http://dx.doi.org/10.1007/bf00475696.

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39

Chrysochos, Nicolas, and Carola Schulzke. "Crystal structure of 1-ethyl-3-(2-oxo-1,3-dithiol-4-yl)quinoxalin-2(1H)-one." Acta Crystallographica Section E Crystallographic Communications 74, no. 7 (2018): 901–4. http://dx.doi.org/10.1107/s2056989018007892.

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The title compound I, C13H10N2O2S2, crystallizes in the monoclinic space group C2/c with eight molecules in the unit cell. Excluding for the ethyl substituent, the molecule of I adopts a nearly coplanar conformation (r.m.s. deviations is 0.058 Å), which is supported by the intramolecular C—H...O hydrogen-bonding interaction between the two ring systems [C...O = 2.859 (3) Å]. In the crystal, the molecules form dimeric associates via two bifurcated C—H...O hydrogen-bonding interactions between an ene hydrogen atom and a carbonyl functional group of an adjacent molecule [C...O = 3.133 (3) Å] and

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40

Trinka, Eugen, and Mar Carreňo. "Reflections on the Use of Perampanel in Epilepsy – Lessons from the Clinic and Real-world Evidence." European Neurological Review 12, no. 01 (2017): 17. http://dx.doi.org/10.17925/enr.2017.12.01.17.

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Optimal epilepsy management includes five important elements: rational treatment selection, efficacy, off-target effects, adherence and interactions and dosing issues. Perampanel (2-[2-oxo-1-phenyl-5-pyridin-2-yl-1,2-dihydropyridin-3-yl]benzonitrile; E2007) is the first potent, selective, orally-active non-competitive alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) receptor antagonist approved for the treatment of patients with epilepsy. Results from randomised controlled trials and real-world studies of refractory epilepsy populations treated with perampanel showed effective f

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41

Kennedy, Alan R., Maurice O. Okoth, David B. Sheen, John N. Sherwood, Simon J. Teat, and Ranko M. Vrcelj. "Cephalexin: a channel hydrate." Acta Crystallographica Section C Crystal Structure Communications 59, no. 11 (2003): o650—o652. http://dx.doi.org/10.1107/s0108270103022649.

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The antibiotic cephalexin [systematic name: D-7-(2-amino-2-phenylacetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid] forms a range of isomorphic solvates, with the maximum hydration state of two water molecules formed only at high relative humidities. The water content of the structure reported here (C16H17N3O4S·1.9H2O) falls just short of this configuration, having three independent cephalexin molecules, one of which is disordered, and 5.72 observed water molecules in the asymmetric unit. The facile nature of the cephalexin solvation/desolvation process is found t

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42

Gakovic, Andrea, Maja Djurendic-Brenesel, Evgenija Djurendic, Katarina Penov-Gasi, and Marija Sakac. "Synthesis of some 16,17-secoandrost-5-ene derivatives." Chemical Industry 64, no. 2 (2010): 81–84. http://dx.doi.org/10.2298/hemind100212009g.

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Starting from 3?-acetoxy-17-oxo-16,17-secoandrost-5-ene-16-nitrile (1), 3?-acetoxy-16,17-secoandrost-5-ene-16-nitrile (4) was synthesized by a three-stage procedure. First, the formyl group of compound 1 was reduced, to yield the alcohol 2. Compound 2 was further transformed to the mesyloxy derivative 3, whose reduction with NaBH3CN gave compound 4. Apart from compound 4 as the main reaction product, two additional products were obtained, for which the GC/MS analysis suggested that they are 8(14) and 14 derivatives of compound 4. Compound 4 was transformed into 3?-hydroxy-16,17-sesoandrost-5-e

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43

Yates, Peter, and Magdy Kaldas. "The synthesis of norbornanes with functionalized carbon substituents at a bridgehead. 1-(3-Oxonorborn-1-yl)ethanone and 1-(3-oxonorborn-1-yl)-2-propanone." Canadian Journal of Chemistry 70, no. 5 (1992): 1492–505. http://dx.doi.org/10.1139/v92-185.

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Treatment of 2-norobornene-1-carboxylic acid (7) with one equivalent of methyllithium in ether followed by a second molar equivalent after dilution with tetrahydrofuran gave 1-(norborn-2-en-lyl)ethanone (10) and only a trace of the tertiary alcohol 11. Reaction of 7 with formic acid followed by hydrolysis gave a 4:3 mixture of exo-3- and exo-2-hydroxynorbornane-1-carboxylic acid (16 and 17), whereas oxymercuration–demercuration gave only the exo-3-hydroxy isomer 16. Oxidation of 16 and 17 gave 3- and 2-oxonorbornane-1-carboxylic acid (27 and 29), respectively. Oxymercuration–demercuration of 1

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44

Mariam, Irfana, Mehmet Akkurt, Shahzad Sharif, Syed Kamran Haider, and Islam Ullah Khan. "7-Benzenesulfonamido-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid methanol solvate." Acta Crystallographica Section E Structure Reports Online 65, no. 8 (2009): o1737. http://dx.doi.org/10.1107/s1600536809024726.

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45

Sheverdov, V. P., O. E. Nasakin, A. Yu Andreev, V. L. Gein, and V. A. Tafeenko. "Synthesis of methyl 3-acyl-6-amino-5-cyano-4-phenyl-4H-pyran-2-carboxylates and their rearrangement into 2-hydroxy-4-[hydroxy(R)methylidene]-3-oxo-5-phenylcyclopent-1-ene-1-carbonitriles." Russian Journal of Organic Chemistry 47, no. 7 (2011): 1117–18. http://dx.doi.org/10.1134/s1070428011070244.

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46

Liu, Yixi, C. Houston Wiedle, Peggy J. Brodie, et al. "Antiproliferative Diterpenes from a Malleastrum sp. from the Madagascar dry forest [1]." Natural Product Communications 10, no. 9 (2015): 1934578X1501000. http://dx.doi.org/10.1177/1934578x1501000905.

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An ethanol extract of leaves of the plant species Malleastrum sp. collected in northern Madagascar afforded the new clerodane diterpene 18-oxo-cleroda-3,13-dien-16,15-olide (1), together with the three known clerodane diterpenes 16,18-dihydroxykolavenic acid lactone (2), solidagolactone (3) and (-)-kolavenol (4), and the known labdane diterpene 3-oxo-ent-Iabda-8(17),13-dien-15,16-olide (5). Compounds 1, 3, and 4 showed moderate antiproliferative activities against the A2780 ovarian cancer cell line, with the IC50 values of 3.01 ± 0.8, 7.84 ± 0.2, and 17.9 ± 3 μM, respectively. The structure el

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47

YOSHIOKA, TAKEO, AZUMA WATANABE, NORITAKA CHIDA, and YASUO FUKAGAWA. "Conversion of OA-6129 B2 into (5R,6R)-6-((R)-1-fluoroethyl)-7-oxo-3-((N.N.N-trimethyl-carbamimidoyl)methyl)thio-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid (88617)." Journal of Antibiotics 42, no. 10 (1989): 1520–22. http://dx.doi.org/10.7164/antibiotics.42.1520.

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48

Abdul-Ridha, Nabeel A., Afraah D. Salmaan, Rita Sabah, Bahjat Saeed, and Najim A. Al-Masoudi. "Synthesis, cytotoxicity and in silico study of some novel benzocoumarin-chalcone-bearing aryl ester derivatives and benzocoumarin-derived arylamide analogs." Zeitschrift für Naturforschung B 76, no. 3-4 (2021): 201–10. http://dx.doi.org/10.1515/znb-2020-0204.

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Abstract The development of new prostate cancer protein receptor cytochrome P450 17A1 inhibitors offers the possibility of generating structures of increased potency. To this end, the chalcone analogs 7 and 8 were prepared from treatment of methyl 3-oxo-3H-benzocoumarin-2-carboxylate (4) with aryl aldehydes. Treatment of 7 and 8 with three anti-inflammatory drugs, flurbiprofen, ketoprofen and ibuprofen, in the presence of POCl3/DMAP gave the ester analogs 9–12. Analogously, treatment of ethyl 3-oxo-3H-benzocoumarin-2-carboxylate (15), prepared previously from 2-hydroxy-1-naphthaldehyde (13) an

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49

KATO, Y., Y. ASANO, and A. J. L. COOPER. "ChemInform Abstract: 3-Hydroxy-2-oxo-1-oxaspiro(4,5)-dec-3-ene, a New Inhibitor of Lactate Dehydrogenase." ChemInform 26, no. 48 (2010): no. http://dx.doi.org/10.1002/chin.199548125.

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50

Nakai, H., M. Takasuka, Y. Ide, Y. Hamada та M. Shiro. "Structure of a 7α-methoxy-1-oxacephem: dichloromethane solvated (−)-(6R,7R)-7-{2-[(difluoromethyl)thio]acetamido}-3-({[1-(2-hydroxyethyl)-1H-tetrazol-5-yl]thio}methyl)-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid". Acta Crystallographica Section C Crystal Structure Communications 43, № 11 (1987): 2153–55. http://dx.doi.org/10.1107/s0108270187088668.

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