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Bibliografías temáticas / Cyclohexanedione-1,3(Methyl-2 Oxo-3p Butyl-2)|Ent

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Literatura académica sobre el tema "Cyclohexanedione-1,3(Methyl-2 Oxo-3p Butyl-2)|Ent"

Autor: Grafiati

Publicado: 14 de julio de 2021

Última modificación: 17 de febrero de 2022

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Artículos de revistas sobre el tema "Cyclohexanedione-1,3(Methyl-2 Oxo-3p Butyl-2)|Ent"

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) were also obtained from the reaction of (6f) and (6g) with lithium diisopropylamide . Compounds (2a) and (2b) were each obtained as a single bridgehead isomer, the relative stereochemistry of ring fusion of which was assigned as cis on the basis of semiempirical molecular orbital calculations. Compound (2c) was obtained as a mixture of cis-and trans-fused bridgehead isomers. The ester (2b) was converted into the herbicide methyl 5,7-dioxo-6-[1-[(prop-2-enyloxy) imino ] butyl]octahydro-3aH-indene-3a-carboxylate (3a).

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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 2α-methyl ketone XVII (chair form) is more stable than its 2β-epimer XVI (boat form): only 9 ± 3% of XVI exists at equilibrium. Conformation of ring A in the unsubstituted 1-ketone I and differences in stability of the boat form in 1,2- and 2,3-disubstituted triterpenoids are discussed.

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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-bicyclo[3.3.0]octane-1-carboxylate (21), which on hydration, diacetylation, and treatment with tri-n-butyltin hydride and azoisobutyronitrile is converted to methyl exo-6-acetoxy-3-acetyl-4,4,exo-8-trimethyl-cis-bicyclo[3.3.0]octane-1-carboxylate (31). Methanolysis of 31. tert-butyldimethylsilylation, and reaction with potassium tert-butoxide in tert-butyl alcohol gives exo-4-tert-butyldimethylsilyloxy-exo-2,6,6-trimethyl[5.3.11,5]undecane-8,10-dione (35). This on treatment with lithium aluminum hydride followed by oxidation and hydrogenation provides the corresponding 10-deoxo compound, 39. Reaction of this with methyllithium, dehydration, and desilylation with hydrogen fluoride in acetonitrile gives a mixture of (±)-α-biotol (1) and (±)-β-biotol (2); desilylation with hydrogen chloride in methanol gives solely (±)-1.

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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 introduced to the cyclopentane ring via the SN2 type nucleophilic substitution of (1 S,2 R,3 R,2′ Z)-3-acetoxy-2-(pent-2′-enyl)cyclopent-4-ene-1-ol with a dialkylcuprate for (+)-12-oxo-PDA.

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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 3-hydroxy-4,4,8-trimethyl-6-oxo-cis-bicyclo[3.3.0]-octa-2,7-diene-1,2-dicarboxylate (30). This, on acetylation, reduction with NaBH4/CeCl3, methanolysis, monodecarbomethoxylation, and hydrogenation, gives methyl endo-6-hydxoxy 4,4-endo-8-trimethyl-3-oxo-cis-bicyclo[3.3.0]octane-1-carboxylate (38), while on reduction with Li/NH3 followed by monodecarbomethoxylation it gives a methyl 6-hydroxy-4,4-exo-8-trimethyl-3-oxo-cis-bicyclo[3.3.0]octane-1-carboxylate (33).

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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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