trans-(±)-2-(phenylthio)cyclohexyl acetate | 14032-06-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: trans-(±)-2-(phenylthio)cyclohexyl acetate
• 英文别名: trans-2-acetoxycyclohexyl phenyl sulfide；trans-2-phenylthiocyclohexyl acetate；2-(phenylthio)cyclohexyl acetate；trans-1-Phenylmercapto-2-acetoxy-cyclohexan；2-(Phenylthio)-cyclohexylacetat；[(1S,2S)-2-phenylsulfanylcyclohexyl] acetate
• CAS: 14032-06-5；16162-54-2；133775-38-9
• 化学式: C₁₄H₁₈O₂S
• 分子量: 250.362
• InChiKey: BKUZICFRZFFPFI-KBPBESRZSA-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

• 作为产物：
  描述：

  OS-phenyl diethylsulfamo(thioperoxoate) 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 1.0h， 生成 trans-(±)-2-(phenylthio)cyclohexyl acetate
  参考文献：
  名称：

  Zefirov, N.S.; Zyk, N.V.; Kutateladze, A.G., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, p. 351 - 360

  摘要：

  DOI：

文献信息

• Diastereoselective Synthesis of -Hydroxy Sulfoxides: Enzymatic and Biomimetic Approaches
  作者：Stefano Colonna、Vincenza Pironti、Francesca Zambianchi、Gianluca Ottolina、Nicoletta Gaggero、Giuseppe Celentano

  DOI：10.1002/ejoc.200600624

  日期：2007.1

  Stereoselectivities of up to 98 % have been found in the enzymatic synthesis of β-hydroxy sulfoxides catalyzed by cyclohexanone monooxygenase (CHMO). The diastereoselectivity of the “one-pot” preparation of the title compounds in the presence of bovine serum albumin has also been investigated. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  在由环己酮单加氧酶 (CHMO) 催化的 β-羟基亚砜的酶促合成中，已发现立体选择性高达 98%。还研究了在牛血清白蛋白存在下“一锅”制备标题化合物的非对映选择性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Highly enantioselective kinetic resolution of trans-2-(phenylthio)cyclohexanol derivatives by immobilized Candida antartica B lipase
  作者：Swapandeep Singh Chimni、Kirandeep Kaur、Neeraj Bala

  DOI：10.1016/j.molcatb.2013.06.006

  日期：2013.12

  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.
• Reactions of mercuric salts with bis(diethylthiocarbamoyl) disulfide and benzenesulfenyl chloride
  作者：Teruaki Mukaiyama、Tadashi Endo、Shinichi Ikenaga、Kaoru Osonoi

  DOI：10.1021/jo01270a016

  日期：1968.6
• PhI(OAc)2/KI mediated 1,2-acetoxysulfenylation of alkenes: facile synthesis of β-acetoxysulfides
  作者：Charoensak Muangkaew、Praewpan Katrun、Patcharaphon Kanchanarugee、Manat Pohmakotr、Vichai Reutrakul、Darunee Soorukram、Thaworn Jaipetch、Chutima Kuhakarn

  DOI：10.1016/j.tet.2013.08.018

  日期：2013.10

  A convenient method for 1,2-acetoxysulfenylation of alkenes using disulfide promoted by (diacetoxyiodo)benzene (PhI(OAc)(2), DIB)/KI was developed. The reaction is highly regioselective for styrene derivatives while aliphatic alkenes lead to a mixture of two regioisomers. (c) 2013 Elsevier Ltd. All rights reserved.
• Generation of cyclohexene-s-phenylepisulfonium fluoborate and its reaction with nucleophilic reagents
  作者：�. A. Vorob'eva、M. Z. Krimer、V. A. Smit

  DOI：10.1007/bf00923720

  日期：1974.12