(1R,2S)-2-(4-methoxybenzyl)cyclohexyl acetate | 112066-40-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1R,2S)-2-(4-methoxybenzyl)cyclohexyl acetate
• 英文别名: trans-2-(4-Methoxybenzyl)-1-cyclohexyl acetate；[(1R,2S)-2-[(4-methoxyphenyl)methyl]cyclohexyl] acetate
• CAS: 112066-40-7
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: TZZYDOXCHIHPTM-GOEBONIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-(4-methoxybenzyl)cyclohexyl acetate 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1R,2S)-2-(4-methoxy-benzyl)-cyclohexyl ester
  参考文献：
  名称：

  Application of ionic liquids in enzymic resolution by hydrolysis of cycloalkyl acetates

  摘要：

  A comparative study was performed in the enzymic resolution of the isomers of 2-(4-methoxybenzyl)cyclohexyl acetates 1 and 2. The investigation consisted in application of three commercially available lipases (Novozyme 435, Lipozyme IM and non-immobilized powdered lipase from Candida antarctica), two ionic liquids (1-butyl-4-methylpyridinium chloride and 1,3-dimethylimidazolinium methyl sulfate), three modifications of the reaction conditions and two respective isomers of the racemic substrate (1 and 2), and resulted in our finding the appropriate conditions to get both of the products, stereoisomers of 2-(4-methoxybenzyl)cyclohexanol (3; 1S,2S) or (5; 1S,2R), and (in some cases) also the stereoisomers of the deracemized substrate (4; 1 R,2R) or (6; 1 R,2S) with high or acceptable enantiomeric purity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.045
• 作为产物：
  描述：

  环己醇,2-[(4-甲氧苯基)甲基]-,(1S,2S)- 在 吡啶 、 phosphate buffer 、 immobilized Novozyme 435 作用下， 反应 72.0h， 生成 (1R,2S)-2-(4-methoxybenzyl)cyclohexyl acetate
  参考文献：
  名称：

  Application of ionic liquids in enzymic resolution by hydrolysis of cycloalkyl acetates

  摘要：

  A comparative study was performed in the enzymic resolution of the isomers of 2-(4-methoxybenzyl)cyclohexyl acetates 1 and 2. The investigation consisted in application of three commercially available lipases (Novozyme 435, Lipozyme IM and non-immobilized powdered lipase from Candida antarctica), two ionic liquids (1-butyl-4-methylpyridinium chloride and 1,3-dimethylimidazolinium methyl sulfate), three modifications of the reaction conditions and two respective isomers of the racemic substrate (1 and 2), and resulted in our finding the appropriate conditions to get both of the products, stereoisomers of 2-(4-methoxybenzyl)cyclohexanol (3; 1S,2S) or (5; 1S,2R), and (in some cases) also the stereoisomers of the deracemized substrate (4; 1 R,2R) or (6; 1 R,2S) with high or acceptable enantiomeric purity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.10.045

文献信息

• Highly selective purification of three lipases from Geotrichum candidum 4013 and their characterization and biotechnological applications
  作者：Jana Brabcová、Zuzana Demianová、Jiří Vondrášek、Michal Jágr、Marie Zarevúcka、Jose M. Palomo

  DOI：10.1016/j.molcatb.2013.09.012

  日期：2013.12

  Simple purification steps were used to purify two lipases (Lip1 and Lip2) and one novel lipase (Lip3) produced by Geotrichum candidum 4013. The octyl-Sepharose at low ionic strength was used to adsorbe Lip2 and novel Lip3, by addition of octadecyl-Sepabeads the Lip1 was also adsorbed from the crude mixture. Desorption of proteins with a Triton X-100 gradient or 1% (v/v) Triton X-100 permitted to fully purify Lip1, Lip2 and Lip3 lipases.The identification of Lip1 and Lip2 was confirmed by using mass spectrometry approach and their characterization by molecular modeling approach. CD spectra and fluorescence showed differences in the secondary and tertiary structure; the apparent difference was the presence of 4 extra loops in Lip2 in contrast to Lip1 structure. The Edman degradation together with mass spectrometry revealed the presence of unique peptide AVGGGATLPEK in the novel lipase Lip3. The catalytic properties of the lipases were tested through hydrolysis of p-nitrophenyl esters, triacylglycerols and peracetylated thymidine esters. The enantioselectivity potential of purified lipases was studied for the hydrolyses of trans-2-(4-methoxybenzyl)-1-cyclohexyl acetate, where Lip3 was the only active lipase with an excellent selectivity (ee(p) > 99%, E = 372). The all three purified lipases from G. candidum 4013 have shown promising catalytic properties with biotechnological application. (C) 2013 Elsevier B.V. All rights reserved.
• Enzymic resolution of 2-substituted cyclohexanols through lipase-mediated esterification
  作者：Zdeněk Wimmer、Vasso Skouridou、Marie Zarevúcka、David Šaman、Fragiskos N. Kolisis

  DOI：10.1016/j.tetasy.2004.11.009

  日期：2004.12

  Several lipases were used for the kinetic resolution of the racemic cis- and trans-isomers of 2-(4-methoxybenzyl)cyclohexanol, by lipase-mediated esterification of the substrates to the corresponding acetate isomers. Conversion of the products and the remaining deracemized substrates into diastereoisomeric esters of 3,3,3-trifluoromethyl-2-methoxy-2-phenylpropanoic acid, their analysis by chiral HPLC and assignment of their absolute configurations through their H-1 and F-19 NMR spectra, were the basis of evaluation of the studied enzymic process. Lipase from Rhizomucor miehei (RML) was found to be the most efficient enzyme regarding enantiomeric excess (ee) and yield of the desired products, while resolution by lipase from Rhizopus arrhizus (RAL) resulted in satisfactory ee and lower yields. (C) 2004 Elsevier Ltd. All rights reserved.
• BUDESINSKY, M.;SAMAN, D.;WIMMER, Z., COLLECT. CZECH. CHEM. COMMUN., 1982, 47, N 10, 2763-2767
  作者：BUDESINSKY, M.、SAMAN, D.、WIMMER, Z.

  DOI：——

  日期：——