66964-89-4Relevant academic research and scientific papers
Synthesis of poly(decahydro-2-naphthyl methacrylate)s with different geometric structures and effects of side-group dynamics on polymer properties investigated by thermal and dynamic mechanical analyses and DFT calculations
Ozaki, Anri,Sumita, Koha,Goto, Kunihiro,Matsumoto, Akikazu
, p. 2941 - 2950 (2013/06/05)
We prepared the geometric isomers of decahydro-2-naphthols as the source materials for the synthesis of poly(decahydro-2-naphthyl methacrylate)s [poly(DNMA)-I, -II, -III, and -IV] including alicyclic ester groups with different geometric structures. The geometry and conformational dynamics of the decahydro-2-naphthyl moieties were investigated by NMR spectroscopy and DFT calculations. We synthesized each isomer of the methacrylic monomers, polymerized them, and investigated the optical, thermal, and mechanical properties of poly(DNMA)s with different isomer compositions. The Tg values of the poly(DNMA)s were in the following order: 139.3 C for poly(DNMA)-II 3/g, 1.489, and 42-44, respectively.
Synthesis and Pseudomonas lipase inhibition study of stereoisomers of decahydro-2-naphthyl-N-n-butylcarbamate
Lin, Ming-Cheng,Shen, Yu-Fang,Lin, Gialih
experimental part, p. 1168 - 1176 (2012/06/15)
(2S,4aR,8aS)-Cis,cis-, (2R,4aS,8aR)-cis,cis-, rac-cis,cis-, and rac-trans,cis-decahydro-2-naphthyl-N-n-butylcarbamates are synthesized from condensation of (2S,4aR,8aS)-cis,cis-, (2R,4aS,8aR)-cis,cis-, rac-cis,cis-, and rac-trans,cisdecahydro-2-naphthols, respectively, with n-butyl isocyanate in the presence of triethylamine in dichloromethane. Optically pure (2S,4aR,8aS)-(-)-and (2R,4aS,8aR)-(+)-cis,cis-decahydro-2-naphthols are resolved by the porcine pancreatic lipase-catalyzed acetylation of decahydro-2-naphthols with vinyl acetate in t-butyl methyl ether. Absolute configurations of (2S,4aR,8aS)-(-)-and (2R,4aS,8aR)-(+)-cis,cis-decahydro-2-naphthols are determined from the 19F NMR spectra of their Mosher's ester derivatives. (2S,4aR,8aR)-Trans,cis-and (2R,4aS,8aS)-trans,cis-decahydro-2- naphthols can't be resolved from the porcine pancreatic lipase-catalyzed acetylation of decahydro-2-naphthols with vinyl acetate in t-butyl methyl ether. For the inhibitory potency of Pseudomonas lipase, (2S,4aR,8aS)-cis,cis- decahydro-2-naphthyl-N-n-butylcarbamate is 3.5 times more potent than (2R,4aS,8aR)-cis,cis-decahydro-2-naphthyl-N-n-butylcarbamate; racemic cis,cis-decahydro-2-naphthyl-N-n-butylcarbamate is about the same with trans,cis-decahydro-2-naphthyl-N-n-butylcarbamate. These inhibitors also show similar effects on porcine pancreatic lipase.
Oxidation of trans-Decahydronaphthalene in Acetic Anhydride
Yazu, Kaumasa,Wakabayashi, Takeshige,Nakayama, Tetsuo
, p. 1409 - 1412 (2007/10/02)
The oxidation of trans-decahydronaphthalene (1) was carried out in acetic anhydride with oxygen in the presence of Co(OAc)2, Ce(OAc)3, and NH4Br.Decahydronaphthyl acetates were obtained as main oxidation products in a selectivity of 81 molpercent at 120 degC.In addition, relative reactivities of hydrogen atoms of 1 were determined at temperatures from 90 to 120 degC.
Enantioselectivity of Microbial Hydrolysis of (+/-)-Decahydro-2-naphthyl Acetates. Preparation and Absolute Configurations of Chiral Decahydro-2-naphthols
Oritani, Takayuki,Yamashita, Kyohei,Kabuto, Chizuko
, p. 3689 - 3694 (2007/10/02)
Absolute configurations of chiral decahydro-2-naphthols, which were obtained by microbial hydrolysis of corresponding (+/-)-acetates and chloroacetates, were elucidated by chemical correlation to (4aS,8aS)-trans-octahydro-2(1H)-naphthalenone (5).Decarboxylation of the (-)-α-methylbenzylamine salt of (-)-2-oxo-2,3,4,4a,5,6,7,8-octahydro-4a-naphthalenecarboxylic acid (1a) gave (+)-(S)-4,4a,5,6,7,8-hexahydro-2(3H)-naphthalenone (3), which was reduced with lithium in liquid ammonia to (+)-(4aS,8aS)-trans-octahydro-2(1H)-naphthalenone (5).Catalytic hydrogenation of (-)-3gave (-)-(4aR,8aS)-cis-octahydro-2(1H)-naphthalenone (4), which was already obtained by oxidation of (-)-cis,cis-decahydro-2-naphthol (7) with chromic acid.These results mean that (-)-7 has the 2S,4aR,8aS configuration.Furthermore, the absolute configuration of (-)-7 was confirmed by X-ray analysis of its p-bromobenzoate.
Enzymic Resolution of (+/-)-axial-Alcohols via Asymmetric Hydrolysis of Corresponding Chloroacetates by Microorganisms
Oritani, Takayuki,Ichimura, Michio,Hanyu, Yoshifumi,Yamashita, Kyohei
, p. 2613 - 2618 (2007/10/02)
Asymmetric hydrolysis of chloroacetates of (+/-)-axial-alcohols (+/-)-neomenthol (2), (1RS,4aRS,8aSR)-decahydro-1-naphthol (6) by Trichoderma koningi gave (-)-(1S,3R,4R)-neomenthol (2) (54percent optical purity, o.p.) and (-)-(1R,4aR,8aS)-decahydro-1-naphthol (6) (66percent o.p.) with their enantiomeric chloroacetates.However, the chloroacetate of (2RS,4aRS,8aSR)-decahydro-2-naphthol (10) was hydrolyzed by T. koningi to give the (-)-alcohol (10) (12percent o.p.) with low enantioselectivity.
THALLIUM NITRATE AS A REAGENT FOR THE CONVERSION OF EPOXIDES INTO α-HIDROXY-NITRATE ESTERS AND FOR THE CLEAVAGE OF ALIPHATIC ETHERS
Mincione, E.,Lanciano, F.
, p. 1149 - 1150 (2007/10/02)
Simple as well as steroidal oxiranes are converted into the corresponding α-hidroxy nitrate esters by treatment with Tl(NO3)3 in hexane solution.Moreover aliphatic ethers react with Tl(NO3)3 in acetic anhydride via cleavage of the ethereal bond and formation of the corresponding acetoxy derivatives.
Stereochemistry and Regiochemistry of Electron Impact Thermally and Photolytically Induced Eliminations from 2-Decalyl Acetates
Rej, R. N.,Taylor, C.,Eadon, G.
, p. 126 - 130 (2007/10/02)
Deuterium-labeled compounds are used to define the stereochemistry and regiochemistry of the electron impact induced elimination of acetic acid from trans,trans-2-decalyl acetate and trans,cis-2-decalyl acetate.Both compounds fragment with very predominant abstraction of equatorial hydrogen atoms.Since the trans equatorial hydrogens of the trans,trans acetate cannot be approached within the requisite 1.8 Angstroem by the acetate carbonyl in any boatlike conformer, this result demonstrates that hydrogen abstraction largely occurs from the chair conformer of the cyclohexyl ring.Both compounds fragment with predominant elimination toward C-1 rather than C-3.The regiochemistry of the pyrolysis of the acetates and the photolysis of the corresponding phenylacetates is compared with that of the mass spectral elimination.
