1-acetoxy-2-phenylthiocyclohexane | 133775-38-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-acetoxy-2-phenylthiocyclohexane
• 英文别名: (1R, 2R)-2-(phenylthio)cyclohexyl acetate；1-Acetoxy-2-thiophenylcyclohexan (trans)；(1R,2R)-2-Phenylthio-1-cyclohexyl acetate；[(1R,2R)-2-phenylsulfanylcyclohexyl] acetate
• CAS: 133775-38-9
• 化学式: C₁₄H₁₈O₂S
• 分子量: 250.362
• InChiKey: BKUZICFRZFFPFI-ZIAGYGMSSA-N

物化性质

• 沸点：
  353.6±35.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-acetoxy-2-phenylthiocyclohexane 在 sodium hydroxide 、 sodium periodate 、 硝苯酚 、 calcium carbonate 作用下， 以 甲醇 为溶剂， 反应 21.0h， 生成 (-)-(R)-cyclohex-2-enylacetic acid
  参考文献：
  名称：

  Synthesis of an enantiomerically pure aminoisoquinocarbazole with antiarrhythmic activity via lipase-catalyzed enantioselective transesterification

  摘要：

  Enantiomerically pure (R)-2-cydohexen-1-ol 5 was prepared via lipase-catalyzed enantioselective transesterification of 2-substituted cyclohexanol, and stereospecifically converted to (-)-(2-cyclohexenyl)acetic acid 4. Enantiomerically pure aminoisoquinocarbazole 1 (RS-2135) was synthesized stereoselectively from 4, using an intramolecular Dids-Alder reaction and Curtius rearrangement. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00199-1
• 作为产物：
  描述：

  氧化环己烯 在 potassium carbonate 作用下， 以 甲基叔丁基醚 、 水 为溶剂， 反应 4.0h， 生成 1-acetoxy-2-phenylthiocyclohexane
  参考文献：
  名称：

  Highly enantioselective kinetic resolution of trans-2-(phenylthio)cyclohexanol derivatives by immobilized Candida antartica B lipase

  摘要：

  Candida antartica B (immobilized CAL-B) mediated resolutions of trans-2-(phenylthio)cyclohexanol derivatives using vinyl acetate as acylating agent and MTBE as solvent provide excellent enantioselectivity (up to >99%) and high yield of both the enantiomers in short reaction time. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2013.06.006

文献信息

• Indolobenzoquinoline derivatives, their preparation and their use as anti-arrhythmic drugs
  申请人：Sankyo Company Limited

  公开号：EP0415776A2

  公开（公告）日：1991-03-06

  Optically active compounds of formula (I): in which R1 is hydrogen or alkyl; Xb and Yb are hydrogen or hydroxy; and Z is -NRaRb in which Ra and Rb are hydrogen, alkyl or hydroxyalkyl, or a cyclic amino group; and pharmaceutically acceptable salts thereof have enhanced anti-arrhythmic activity and may be prepared by a stereospecific synthesis process.

  式(I)中的光学活性化合物：其中R1为氢或烷基；Xb和Yb为氢或羟基；Z为-NRaRb，其中Ra和Rb为氢、烷基或羟基烷基，或环状氨基；以及其药学上可接受的盐具有增强的抗心律失常活性，并可通过立体特异性合成过程制备。
• Preparation of optically active cyclohexenol and cyclohexenyl acetic acid via an enzymatic process followed by a rearrangement reaction and their use as intermediates in the synthesis of indolobenzoquinoline derivatives
  申请人：Sankyo Company Limited

  公开号：EP0674008A1

  公开（公告）日：1995-09-27

  A process for the production of optically active compounds of formula (VIII) and III which process comprises the following steps: (a) reaction, in the presence of a lipase, of a dl-trans-cyclohexanol compound of formula (XXI): to give an optically active compound of formula (XXIV) followed by b) an oxidation, c) an elimination and d) a hydrolyzation reaction to give the optically active compound VIII and rearranging the compound VIII with orthoester to the optically active compound III. Compounds VIII and III are intermediates in the synthesis of optically active compounds of formula I

  一种生产式（VIII）和式（III）光学活性化合物的工艺 该工艺包括以下步骤 (a) 式(XXI)的二反式环己醇化合物在脂肪酶存在下进行反应： 得到式（XXIV）的光学活性化合物 然后进行 b) 氧化反应、c) 消去反应和 d) 水解反应，得到光学活性化合物 VIII，并将化合物 VIII 与原酯重新排列，得到光学活性化合物 III。 化合物 VIII 和 III 是合成具有光学活性的式 I 化合物的中间体。
• Copper-Catalyzed 1,2-Hydroxysulfenylation of Alkene Using Disulfide via Cleavage of the S−S Bond
  作者：Nobukazu Taniguchi

  DOI：10.1021/jo060834l

  日期：2006.9.1

  Copper-catalyzed 1,2-hydroxysulfenylation of alkenes can be carried out by the use of disulfides and acetic acid in air. This reaction regio- and anti-selectively gave the corresponding 1,2-acetoxysulfides. Furthermore, the present method enables the use of both organosulfide groups of disulfide.
• Synthesis of enantiomerically pure (R)-2-cycloalken-1-ols using highly enantioselective enzymatic transesterification
  作者：Tetsuya Fukazawa、Toshihiko Hashimoto

  DOI：10.1016/s0957-4166(00)80093-2

  日期：1993.11

  Optically pure (R)-2-cycloalken-1-ols were synthesized via highly enantioselective lipase-catalyzed transesterification of 2-substituted cycloalkanols.
• Zefirov, N. S.; Zyk, N. V.; Kutateladze, A. G., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 11, p. 2212 - 2213
  作者：Zefirov, N. S.、Zyk, N. V.、Kutateladze, A. G.、Lapin, Yu. A.、Chizhov, A. O.

  DOI：——

  日期：——