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Journal articles on the topic 'Bicyclo[3.3.1]nonane'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Brunelli, Michela, Marcus A. Neumann, Andrew N. Fitch, and Asiloé J. Mora. "Temperature phase changes in solid bicyclo[3.3.1]nonane-2,6-dione and bicyclo[3.3.1]nonane-3,7-dione from powder X-ray diffraction data." Journal of Applied Crystallography 40, no. 4 (2007): 702–9. http://dx.doi.org/10.1107/s0021889807028087.

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The crystal structures of bicyclo[3.3.1]nonane-2,6-dione and bicyclo[3.3.1]nonane-3,7-dione have been solved by direct methods and by direct-space simulated annealing, respectively, from powder synchrotron X-ray diffraction data. Both compounds have a transition to a face-centred-cubic orientationally disordered phase (phase I) near 363 K, as shown by differential scanning calorimetry and powder diffraction measurements. Phase II of bicyclo[3.3.1]nonane-2,6-dione, which occurs below 363 K, is monoclinic, space groupC2/c, witha= 7.38042 (4),b= 10.38220 (5),c= 9.75092 (5) Å and β = 95.359 (1)° a

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2

Zhu, Hui, Ya-Nan Yang, Kuo Xu, et al. "Sophopterocarpan A, a novel pterocarpine derivative with a benzotetrahydrofuran-fused bicyclo [3.3.1] nonane from Sophora flavescens." Organic & Biomolecular Chemistry 15, no. 26 (2017): 5480–83. http://dx.doi.org/10.1039/c7ob01261f.

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3

Zaytsev, Andrey V., James E. Pickles, Suzannah J. Harnor, et al. "Concise syntheses of bridged morpholines." RSC Advances 6, no. 59 (2016): 53955–57. http://dx.doi.org/10.1039/c6ra08737j.

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Practical syntheses of 8-oxa-3-aza-bicyclo[3.2.1]octane and 9-oxa-3-aza-bicyclo[3.3.1]nonane, useful intermediates for synthesising kinase inhibitors, were achieved from readily available starting materials, using a solvent-free thermolytic cyclisation for the key step.

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4

Laszlo, Ilona. "The conformation of bicyclo[3.3.1]nonane." Recueil des Travaux Chimiques des Pays-Bas 84, no. 2 (2010): 251–54. http://dx.doi.org/10.1002/recl.19650840213.

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5

Bagdžiūnas, Gintautas, Sigitas Stončius, and Eugenijus Butkus. "Synthesis of Star-Shaped Aromatic Derivatives with Chirality Predetermined by Bicyclo[3.3.1]nonane Framework." Synlett 28, no. 20 (2017): 2790–94. http://dx.doi.org/10.1055/s-0036-1590833.

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Star-shaped aromatic derivatives of bicyclo[3.3.1]nonane with predetermined chirality were synthesized by employing the Suzuki and Sonogashira reactions. The C 3-symmetric trifunctional aromatic derivatives based on the lateral bicyclo[3.3.1]nonene moiety possess unique molecular structures. The chiroptical properties of the star-shaped compounds and the corresponding monomeric derivatives were studied, and the absolute configuration was confirmed by using the empirical octant rule for the carbonyl chromophore and the sector rule for the aromatic chromophore.

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6

Tian, Wen-Jing, Yu-Qin Qiu, Xiao-Jie Jin, et al. "Hypersampsones S–W, new polycyclic polyprenylated acylphloroglucinols from Hypericum sampsonii." RSC Advances 6, no. 56 (2016): 50887–94. http://dx.doi.org/10.1039/c5ra26332h.

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7

Ren, Xiaoli, Yifei Ling, and Jun Luo. "Synthesis of Bicyclo[3.3.1]nonane-2,6,9-trione." Chinese Journal of Organic Chemistry 34, no. 2 (2014): 376. http://dx.doi.org/10.6023/cjoc201309009.

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8

MacCorquodale, Finlay, and John C. Walton. "Formation of bicyclo[3.2.1]octane, bicyclo[4.2.1]nonane, and bicyclo[3.3.1]nonane by transannular radical cyclisations." Journal of the Chemical Society, Chemical Communications, no. 19 (1987): 1456. http://dx.doi.org/10.1039/c39870001456.

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9

Butkus, Eugenius, Arvydas Stoncius, Jule Malinauskiene, Shuji Tomoda, and Daisuke Kaneno. "Stereoelectronic and conformational effects on the stereochemical course of reduction of bicyclo[3.3.1]nonane 1,3-diketones." Canadian Journal of Chemistry 79, no. 11 (2001): 1598–605. http://dx.doi.org/10.1139/v01-131.

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The stereoselectivity of the reduction of bicyclo[3.3.1]nonane 1,3-diketones was studied. The experimental data of π-facial stereoselection of the reduction of the carbonyl group were successfully rationalized by the application of the exterior frontier orbital extension (EFOE) model. The observed facial diastereoselectivity of the carbonyl reduction of bicyclo[3.3.1]nonane diketones could be reasonably explained by the ground-state facial anisotropy of the frontier orbital extension, steric effects, and the intrinsic reactivity of carbonyl groups. Although the EFOE density and PDAS values pre

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10

Yang, Jae-Deuk, Moon-Soo Kim, Miai Lee, Woonphil Baik, and Sangho Koo. "Highly Efficient Synthesis of Bicyclo[3.3.1]nonane Skeleton." Synthesis 2000, no. 06 (2000): 801–4. http://dx.doi.org/10.1055/s-2000-6275.

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11

Inouye, Yoshinobu, Tsutomu Kojima, Jun Owada, and Hiroshi Kakisawa. "Preparation of Bicyclo[3.3.1]nonane-2,4-dione Derivatives." Bulletin of the Chemical Society of Japan 60, no. 12 (1987): 4369–75. http://dx.doi.org/10.1246/bcsj.60.4369.

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12

Skancke, Per N. "An ab initio study of bicyclo[3.3.1]nonane." Journal of Molecular Structure: THEOCHEM 151 (May 1987): 11–14. http://dx.doi.org/10.1016/0166-1280(87)85039-x.

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13

Malinauskieneė, Juleė, Petras Kadziauskas, Albertas Malinauskas, and Juozas Kulys. "Enzymatic Enantioseparation of Bicyclo[3.3.1]nonane-2,6-diones." Monatshefte für Chemie / Chemical Monthly 130, no. 12 (1999): 1513–17. http://dx.doi.org/10.1007/s007060050311.

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14

Alkauskas, A., J. Ceponkus, B. Mikulskiene, V. Aleksa, E. Butkus, and V. Sablinskas. "Conformational stability of bicyclo[3.3.1]nonane-2,6-dione and bicyclo[3.3.1]nonane-2,9-dione: ab initio calculations and vibrational spectroscopy studies." Journal of Molecular Structure 563-564 (May 2001): 517–21. http://dx.doi.org/10.1016/s0022-2860(00)00834-6.

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15

Williams, Steven Gareth, Mohan Bhadbhade, Roger Bishop, and Alison Thavary Ung. "Synthesis and Crystal Structure of Unexpected (1S,4R,5R,6S)-4-Cyano-2,2,6-trimethyl-3-azabicyclo[3.3.1]nonan-6-yl Acetate." Australian Journal of Chemistry 70, no. 12 (2017): 1269. http://dx.doi.org/10.1071/ch17270.

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The reaction of (–)-β-pinene with KCN under a mild bridged Ritter reaction gave (1S,5R,6S)-2,2,6-trimethyl-3-aza-bicyclo[3.3.1]non-3-en-6-yl acetate that subsequently reacted to provide an unexpected (1S,4R,5R,6S)-4-cyano-2,2,6-trimethyl-3-azabicyclo[3.3.1]nonane-6-yl acetate. The structure of the compound was determined by high-resolution mass spectrometry, and IR and NMR spectroscopy and confirmed by single crystal X-ray crystallography. The compound crystallises in the monoclinic P21 space group, with unit cell parameters a 8.6120 (17), b 7.4570 (15), c 11.189 (2) Å, and β 110.16 (3)°.

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16

Vaneesa Nagalingam, Sree, Janet Wong Pik Ching, Mohammed Khaled bin Break, M. Ibrahim M. Tahir, and Teng-Jin Khoo. "AP212121polymorph of (+)-clusianone." Acta Crystallographica Section E Structure Reports Online 69, no. 12 (2013): o1799—o1800. http://dx.doi.org/10.1107/s1600536813031036.

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The title compound, C33H42O4[systematic name: (1S,5S,7R)-3-benzoyl-4-hydroxy-8,8-dimethyl-1,5,7-tris(3-methylbut-2-enyl)bicyclo[3.3.1]nona-3-ene-2,9-dione], has a central bicyclo[3.3.1]nonane-2,4,9-trione surrounded by tetraprenylated and benzoyl groups. The compound was recrystallized several times in methanol using both a slow evaporation method and with a crystal-seeding technique. This subsequently produced diffraction-quality crystals which crystallize in the orthorhombic space groupP212121, in contrast to a previous report of a structure determination in thePna21space group [McCandlishet

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17

Musalov, Maxim V., Vladimir A. Potapov, and Svetlana V. Amosova. "Efficient Synthesis of a New Family of 2,6-Disulfanyl-9-Selenabicyclo[3.3.1]Nonanes." Molecules 26, no. 10 (2021): 2849. http://dx.doi.org/10.3390/molecules26102849.

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The efficient synthesis of a new family of 2,6-disulfanyl-9-selenabicyclo[3.3.1]nonanes in high yields has been developed based on 9-selenabicyclo[3.3.1]nonane-2,6-dithiolate anion generated from bis-isothiouronium salt of 2,6-dibromo-9-selenabicyclo[3.3.1]nonane. The derivatives of 2,6-disulfanyl-9-selenabicyclo[3.3.1]nonane containing alkyl, allyl and benzyl moieties have been prepared in 90–99% yields by nucleophilic substitution of 9-selenabicyclo[3.3.1]nonane-2,6-dithiolate anion with alkyl, allyl and benzyl halides. The reaction of nucleophilic addition of 9-selenabicyclo[3.3.1]nonane-2,

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18

Ahlenstiel, Eckart, Wolfgang Kliegel, Steven J. Rettig, and James Trotter. "Structural studies of organoboron compounds. LVII. Synthesis and structure of bicyclic boron-nitrogen betaines. 1-Methyl-5-(3-nitrophenyl)-4,6,9-trioxa-1-azonia-5-boratabicyclo[3.3.1]nonane and 3,3,4-trimethyl-1-(3-nitrophenyl)-2,6,7-trioxa-3-azonia-1-boratabicyclo[2.2.2]octane." Canadian Journal of Chemistry 71, no. 2 (1993): 263–71. http://dx.doi.org/10.1139/v93-038.

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The syntheses and structures of the bicyclic boron-nitrogen betaines 1-methyl-5-(3-nitrophenyl)-4,6,9-trioxa-1-azonia-5-boratabicyclo[3.3.1]nonane, 7a, and 3,3,4-trimethyl-1-(3-nitrophenyl)-2,6,7-trioxa-3-azonia-1-boratabicyclo[2.2.2]-octane, 14a, are reported. Crystals of 7a are orthorhombic, a = 20.256(2), b = 37.652(2), c = 6.642(1) Å, Z = 16, space group Fdd2, and those of 14a are orthorhombic, a = 21.402(2), b = 11.334(3), c = 11.248(2) Å, Z = 8, space group Pbca. The structures were solved by direct methods and were refined by full-matrix least-squares procedures to R = 0.038 and 0.045 (

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19

Anholeti, Maria Carolina, Selma R. de Paiva, Maria Raquel Figueiredo, and Maria Auxiliadora C. Kaplan. "Chemosystematic aspects of polyisoprenylated benzophenones from the genus Clusia." Anais da Academia Brasileira de Ciências 87, no. 1 (2015): 289–301. http://dx.doi.org/10.1590/0001-3765201520140564.

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Benzophenone derivatives are special metabolites that arouse great scientific interest. The Clusiaceae family is known for producing large amounts of benzophenone derivatives with several isoprene residues on their structures, which are responsible for the observed complexity and structural variety in this class of substances, and also contribute to their biological activities. Clusia is an important genus belonging to Clusiaceae, with 55 different polyisoprenylated benzophenones identified so far. These substances were analyzed from biosynthetic and chemosystematic points of view, allowing th

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20

Johns, SR, JA Lamberton, TC Morton, H. Suares, and RI Willing. "Campnosperma Exudates. The Optically Active Long Chain 5-Hydroxycyclohex-2-Enones and Long-Chain Bicyclo[3.3.1]Nonane-3,7-Diones." Australian Journal of Chemistry 40, no. 1 (1987): 79. http://dx.doi.org/10.1071/ch9870079.

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Re-examination of the optically active long-chain 5-hydroxycyclohex-2-enones of Campnosperma species has confirmed the former structural assignments, except that in Tigaso oil both the 5- hydroxycyclohex-2-enones and the phenolic components contain a significant (35-40%) proportion of compounds with di-unsaturation in the C19-chain. Further study has been made of the conversion of (-)-endo-4-hexadecyl-l-hydroxybicyclo[3.3.l]nonane-3,7-dione (10) into a mixture of an optically inactive and optically active β- diketones. The major product from this reaction is (�)-5-(1-acetylheptadecy1)cyclohexa

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21

Labanauskas, L., A. Zilinskas, S. Visniakova, et al. "Synthesis of bicyclo[3.3.1]nonane derivatives containing fused heterocyclic rings." Arkivoc 2008, no. 15 (2008): 256–61. http://dx.doi.org/10.3998/ark.5550190.0009.f22.

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22

Mohr, Peter. "Synthesis of (−)-endo-1,3-dimethyl-2,9-dioxa-bicyclo [3.3.1]nonane." Tetrahedron Letters 32, no. 20 (1991): 2223–24. http://dx.doi.org/10.1016/s0040-4039(00)79686-9.

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23

Figueroa, Lauro, Alejandra Garcimarero, Rolando Garcia, et al. "Design and Synthesis of Two Bicyclo[3.3.1]nonane-steroid Derivatives." Chemistry Journal of Moldova 15, no. 1 (2020): 75–85. http://dx.doi.org/10.19261/cjm.2019.657.

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24

Mohr, Peter, and Christoph Tamm. "Synthesis of endo-1,3-dimethyl-2,9-dioxa-bicyclo [3.3.1.] nonane." Tetrahedron Letters 28, no. 4 (1987): 395–96. http://dx.doi.org/10.1016/s0040-4039(00)95737-x.

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25

Yang, Jae-Deuk, Moon-Soo Kim, Miai Lee, Woonphil Baik, and Sangho Koo. "ChemInform Abstract: Highly Efficient Synthesis of Bicyclo[3.3.1]nonane Skeleton." ChemInform 31, no. 40 (2000): no. http://dx.doi.org/10.1002/chin.200040073.

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26

Miyazawa, Mitsuo, Masahiro Nobata, Shigeaki Okamura, Osamu Muraoka, Genzoh Tanabe, and Hiromu Kameoka. "Stereoselective reduction of (±)-bicyclo[3.3.1]nonane-2,6-dione by microorganisms." Journal of Chemical Technology & Biotechnology 71, no. 4 (1998): 281–84. http://dx.doi.org/10.1002/(sici)1097-4660(199804)71:4<281::aid-jctb837>3.0.co;2-e.

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27

Fronczek, F. R., J. G. Garcia, and M. L. McLaughlin. "9-(2,4-Cyclopentadienylidene)bicyclo[3.3.1]nonane, a ring-strained pentafulvene." Acta Crystallographica Section C Crystal Structure Communications 46, no. 6 (1990): 1181–83. http://dx.doi.org/10.1107/s0108270190001081.

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28

Klaić, Lada, Jelena Veljković, and Kata Mlinarić-Majerski. "CONVENIENT SYNTHESIS OF NOVEL 1,3,7-TRISUBSTITUTED BICYCLO[3.3.1]NONANE DERIVATIVES." Synthetic Communications 32, no. 1 (2002): 89–97. http://dx.doi.org/10.1081/scc-120001513.

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29

Mori, Kenji, Shuichi Takayama, and Masani Kido. "Reduction of bicyclo[3.3.1]nonane-2,8-diones with baker's yeast." Bioorganic & Medicinal Chemistry 2, no. 6 (1994): 395–401. http://dx.doi.org/10.1016/0968-0896(94)80006-5.

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30

MOMOSE, Takefumi, Osamu MURAOKA, and Kikuo MASUDA. "Bicyclo[3.3.1]nonanes as synthetic intermediates. XV. Ring enlargement of bicyclo[3.3.1]nonane-2,6-dione and bicyclo[3.3.1]nonan-2-one; Revision of the literature." CHEMICAL & PHARMACEUTICAL BULLETIN 37, no. 6 (1989): 1645–46. http://dx.doi.org/10.1248/cpb.37.1645.

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31

Uwamori, Masahiro, and Masahisa Nakada. "Collective Total Synthesis of PPAPs: Total Synthesis of Clusianone via Intramolecular Cyclopropanation." Natural Product Communications 8, no. 7 (2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800721.

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The total synthesis of clusianone was accomplished through the stereoselective construction of a bicyclo[3.3.1]nonane derivative via a three-step sequence which has been utilized for the total syntheses of nemorosone garsubellin A and hyperforin: intramolecular cyclopropanation formation of a geminal dimethyl group and regioselective ring opening of cyclopropane. Further elaboration including chemo- and stereoselective hydrogenation to generate the C7 stereogenic center and cross-metathesis to construct prenyl groups in the side-chains was employed to complete the total synthesis of clusianone

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32

Mazzeo, Giuseppe, Sergio Abbate, Stefan E. Boiadjiev, David A. Lightner, and Giovanna Longhi. "Vibrational Circular Dichroism Detects Symmetry Breaking due to Conformational Mobility in C2-Symmetry Chiral Molecules and Provides Further Insight into Inter-Chromophoric Interactions." Symmetry 12, no. 11 (2020): 1752. http://dx.doi.org/10.3390/sym12111752.

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Bicyclo[3.3.1]nonane-2,6-dione (1) and bicyclo[3.3.1]nona-3,7-diene-2,6-dione (2) have been examined by vibrational circular dichroism (VCD), which, as for most C2-symmetric systems, exhibits strong VCD signals. In the case of 2, VCD signals are stronger and sharper with several bisignate doublets; for 1, signals are less intense and broader. The VCD and IR spectra are excellently predicted by DFT calculations: only one conformer is present for 2, while for 1, three main conformers, related through concerted skeleton torsional motions are present (two of them being interchanged by C2-rotation)

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33

Visniakova, S., A. Zilinskas, and S. Tumkevicius. "Synthesis of 1,10-phenanthrolines fused with bicyclo[3.3.0]octane and bicyclo[3.3.1]nonane frameworks." Chemistry of Heterocyclic Compounds 48, no. 6 (2012): 943–49. http://dx.doi.org/10.1007/s10593-012-1081-4.

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34

YAMAZAKI, TAKAO, KATSUHIDE MATOBA, TOSHIYUKI ITOOKA, MASARU CHINTANI, TAKEFUMI MOMOSE, and OSAMU MURAOKA. "An efficient and practical synthesis of bicyclo[3.3.1]nonane-2,4-diones." CHEMICAL & PHARMACEUTICAL BULLETIN 35, no. 8 (1987): 3453–59. http://dx.doi.org/10.1248/cpb.35.3453.

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35

Ma, Kuangbiao, Jan W. Bats, and Matthias Wagner. "(2,2′-Bipyridyl-N,N′)(bicyclo[3.3.1]nonane-C1,C5)boronium trifluoromethanesulfonate." Acta Crystallographica Section E Structure Reports Online 57, no. 9 (2001): o846—o848. http://dx.doi.org/10.1107/s1600536801013083.

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36

SPREITZER, H. "ChemInform Abstract: Synthesis of 9,9-Dimethyl-2-oxa-bicyclo(3.3.1)nonane." ChemInform 22, no. 1 (2010): no. http://dx.doi.org/10.1002/chin.199101254.

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37

Averina, N. V., G. S. Borisova, A. A. Borisenko, and N. S. Zefirov. "ChemInform Abstract: Photochemistry of 3,7-Bis(arylmethylene)bicyclo[3.3.1]nonane Derivatives." ChemInform 33, no. 12 (2010): no. http://dx.doi.org/10.1002/chin.200212282.

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38

Zilinskas, A., and L. Labanauskas. "Synthesis of new heterocyclic systems containing the bicyclo-[3.3.1]nonane fragment." Chemistry of Heterocyclic Compounds 43, no. 7 (2007): 936–37. http://dx.doi.org/10.1007/s10593-007-0147-1.

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39

Beck, Janina, Olaf Fuhr, Martin Nieger, and Stefan Bräse. "A versatile Diels–Alder approach to functionalized hydroanthraquinones." Royal Society Open Science 7, no. 11 (2020): 200626. http://dx.doi.org/10.1098/rsos.200626.

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The synthesis of highly substituted hydroanthraquinone derivatives with up to three stereogenic centres via a Diels–Alder reaction, starting from easily accessible 2-substituted naphthoquinones, is described. The [4+2]-cycloaddition is applicable for a broad range of substrates, runs under mild conditions and results in high yields. The highly regioselective outcome of the reactions is enabled by a benzoyl substituent at C2 of the dienophiles. The obtained hydroanthraquinones can be further modified and represent ideal substrates for follow-up intramolecular coupling reactions to create unique

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40

Goddard-Borger, Ethan D., Brian W. Skelton, Robert V. Stick, and Allan H. White. "The Conformation of Some 1,6-Disulfide-Bridged D-Hexopyranoses." Australian Journal of Chemistry 58, no. 3 (2005): 199. http://dx.doi.org/10.1071/ch04291.

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The use of 1H NMR spectroscopy, in tandem with X-ray crystallography, has cast light on the conformation of the 1,6-disulfide-bridged derivatives of d-gluco-, d-manno-, d-allo-, d-galacto-, and d-talo-pyranose. A similar investigation was performed on the thiosulfinate derived from the d-gluco disulfide. Single-crystal X-ray structure determinations are reported for (1S,5S,6S,7S,8R)-6,7,8-tribenzoyloxy-9-oxa-2,3-dithiabicyclo[3.3.1]nonane, (1S,5S,6S,7R,8R)-6,7,8-tribenzoyloxy-9-oxa-2,3-dithiabicyclo[3.3.1]nonane, and (1S,2S,5S,6S,7S,8R)-6,7,8-triacetoxy-9-oxa-2,3-dithiabicyclo[3.3.1]nonane 2-o

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41

Majumdar, Krishna C., and Anup K. Kundu. "Pyridine hydrobromide perbromide mediated regioselective heterocyclization of ortho-cyclohexenyl phenols." Canadian Journal of Chemistry 73, no. 10 (1995): 1727–32. http://dx.doi.org/10.1139/v95-211.

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A number of 3,4-benzo-9-bromo-2-oxabicyclo[3.3.1]nonanes (9a–h) are synthesized in almost quantitative yields by regioselective heterocyclization of ortho-cyclohexenyl phenols (8a–h). The structures of 3,4-benzo-9-bromo-2-oxabicyclo[3.3.1]nonane 9 have been unambiguously settled by the synthesis of 9-chloromercuri-3,4-(4′-methoxybenzo)-2-oxabicyclo[3.3.1]nonane 13, which has an X-ray determined structure, and by converting 13 to product 9c with bromine in sunlight in 45% yield. The 6-chloro-2-cyclohexenenyl phenol 8i and 2-cyclohexenyl-4-methyl phenol 8j failed to give any cyclic product but i

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42

Butkus, Eugenius, та Birute Bielinyte-Williams. "Divergent Pathways of Reaction Between Cyclohexanone Enamines and α,β-Unsaturated Acid Chlorides". Collection of Czechoslovak Chemical Communications 60, № 8 (1995): 1343–56. http://dx.doi.org/10.1135/cccc19951343.

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The reaction of cyclohexanone enamines with α,β-unsaturated acid chlorides and 2- and 3-chloropropanoyl chlorides under various conditions has been investigated. a,ae-Annulation of enamines Ia-Ie occurs on treatment with chlorides IIa-IId or 3-chloropropanoyl chloride to give bicyclo[3.3.1]nonane-2,9-dione derivatives III. The formation of isomeric bicyclononanediones IIIe and IIIh and chromanones VIIIa and VIIIb in the reaction of enamines derived from substituted cyclohexanones suggests that the cyclization might proceed also by another pathway than via [3,3] sigmatropic rearrangement. Based

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Lauro, Figueroa-Valverde, Rosas-Nexticapa Marcela, Lopez-Ramos Maria, et al. "Synthesis of a New Dioxaspiro[bicyclo[3.3.1]nonane-oxabicyclo[6.2.0]deca- 1(10),8-dien-4-one Derivative Using Some Chemical Strategies." Letters in Organic Chemistry 17, no. 5 (2020): 393–402. http://dx.doi.org/10.2174/1570178617666191116123359.

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Abstract:

There are several protocols for the preparation of bicyclic derivatives; however, some methods use dangerous and require special conditions. The aim of this study was to synthesize a new Dioxaspiro[ bicyclo[3.3.1]nonane-oxabicyclo[6.2.0]-deca-1(10), 8-dien-4-one (compound 8). Compound 8 was prepared using some reactions such as; i) etherification, ii) reduction, iii) amidation, iv) imination and v) 2+2 addition. The chemical structure of 8 and its intermediaries were completely characterized by spectroscopic techniques and elemental analysis. The synthesis showed a yield of 85% for compound 8.

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Kiryukhin, M. V., E. V. Nurieva, D. V. Shishov, et al. "Synthesis of adamantane and bicyclo[3.3.1]nonane derivatives with the oxetane moiety." Moscow University Chemistry Bulletin 62, no. 5 (2007): 281–85. http://dx.doi.org/10.3103/s0027131407050148.

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Santos, M. H., N. L. Speziali, T. J. Nagem, and T. T. Oliveira. "Epiclusianone: a New Natural Product Derivative of Bicyclo[3.3.1]nonane-2,4,9-trione." Acta Crystallographica Section C Crystal Structure Communications 54, no. 12 (1998): 1990–92. http://dx.doi.org/10.1107/s0108270198006477.

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Kocór, Marian, and Beata Bersz. "Synthesis of bridged steroids with a bicyclo [3.3.1.] nonane ring a system." Tetrahedron 43, no. 9 (1987): 2129–34. http://dx.doi.org/10.1016/s0040-4020(01)86794-6.

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MOHR, P. "ChemInform Abstract: Synthesis of (-)-Endo-1,3-dimethyl-2,9-dioxa-bicyclo(3.3.1)nonane." ChemInform 23, no. 10 (2010): no. http://dx.doi.org/10.1002/chin.199210196.

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Klaic, Lada, Jelena Veljkovic, and Kata Mlinaric-Majerski. "ChemInform Abstract: Convenient Synthesis of Novel 1,3,7-Trisubstituted Bicyclo[3.3.1]nonane Derivatives." ChemInform 33, no. 24 (2010): no. http://dx.doi.org/10.1002/chin.200224091.

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Taylor, Richard J. K., Stephen M. Turner, and David C. Horwell. "A new intramolecular aldol based route to benzannelated bicyclo[3.3.1]nonane derivatives." Journal of the Chemical Society, Chemical Communications, no. 5 (1990): 406. http://dx.doi.org/10.1039/c39900000406.

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Pisarev, Sergey A., Dmitry A. Shulga, Vladimir A. Palyulin, and Nikolay S. Zefirov. "Lone pairs vs. covalent bonds: conformational effects in bicyclo[3.3.1]nonane derivatives." Structural Chemistry 30, no. 2 (2018): 509–22. http://dx.doi.org/10.1007/s11224-018-1240-z.

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