(1S, 2S)-2-(phenylthio)cyclohexanol | 133576-46-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (1S, 2S)-2-(phenylthio)cyclohexanol
• 英文别名: 2-(phenylthio)cyclohexanol；trans-2-(phenylsulfanyl)cyclohexanol；(+)-trans-(1S,2S)-2-(phenylthio)-1-cyclohexanol；(1S,2S)-2-phenylthio-1-cyclohexanol；(+)-trans-(1S,2S)-2-(phenylthio)cyclohexan-1-ol；(+)-trans-2-phenylsulfanyl-1-cyclohexanol；trans-2-(phenylthio)cyclohexanol；(1S,2S)-2-(phenylsulfanyl)cyclohexan-1-ol；(1S,2S)-2-phenylsulfanylcyclohexan-1-ol
• CAS: 133576-46-2
• 化学式: C₁₂H₁₆OS
• 分子量: 208.324
• InChiKey: FLFDJSCCPRMYPE-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S, 2S)-2-(phenylthio)cyclohexanol 在 sodium hydroxide 、 sodium periodate 、 硝苯酚 、 calcium carbonate 作用下， 以 甲醇 、 异丙醚 为溶剂， 反应 45.0h， 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 (1S, 2S)-2-(phenylthio)cyclohexanol
  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

• Facile Room-Temperature MgBr₂· OEt₂-Catalyzed Thiolysis of Epoxides Under Solvent-Free Conditions
  作者：Mohammad M. Mojtahedi、M. Saeed Abaee、Mohammad Bolourtchian、Hassan Abbasi

  DOI：10.1080/10426500601088697

  日期：2007.2.15

  Solvent-free ring opening of 1,2-epoxides with aromatic and aliphatic thiols under 1 mol% magnesium bromide ethyl etherate catalysis affords rapid formation of β-hydroxy sulfides at ambient temperature with excellent yields. Nucleophilic attack of the thiols occurs regioselectively at the less hindered position of the epoxides.

  在 1 mol% 溴化镁乙基醚合物催化下，1,2-环氧化物与芳香族和脂肪族硫醇的无溶剂开环可在环境温度下以优异的产率快速形成 β-羟基硫化物。硫醇的亲核攻击区域选择性地发生在环氧化物的受阻较小的位置。
• Cyanuric Chloride: an Efficient Catalyst for Ring Opening of Epoxides with Thiols Under Solvent-Free Conditions
  作者：Babasaheb P. Bandgar、Neeta S. Joshi、Vinod T. Kamble、Sanjay S. Sawant

  DOI：10.1071/ch07079

  日期：——

  2,4,6-Trichloro-1,3,5-triazine-catalyzed convenient and efficient ring opening of epoxides with thiols under solvent-free conditions is described. Short reaction time, mild reaction conditions, inexpensive and readily available catalyst, and excellent yields of products are attractive features of this methodology.

  本研究描述了在无溶剂条件下，2,4,6-三氯-1,3,5-三嗪催化环氧化物与硫醇进行便捷高效的开环反应。反应时间短、反应条件温和、催化剂廉价易得、产物收率极高，这些都是该方法的诱人之处。
• Regioselective ring opening of epoxides by nucleophiles mediated by lithium bistrifluoromethanesulfonimide
  作者：Janine Cossy、Véronique Bellosta、Claire Hamoir、Jean-Roger Desmurs

  DOI：10.1016/s0040-4039(02)01533-2

  日期：2002.9

  In the presence of LiNTf2, epoxides undergo ring opening with high regioselectivity and in good yield when they are treated with nucleophiles such as amines, hydrazines and thiophenol.

  在LiNTf 2的存在下，当用亲核试剂如胺，肼和苯硫酚处理时，环氧化物以高的区域选择性和高收率进行开环。
• N-acylsulfonamide apoptosis promoters
  申请人：——

  公开号：US20020055631A1

  公开（公告）日：2002-05-09

  N-Benzoyl arylsulfonamides having the formula 1 are BCL-Xl inhibitors and are useful for promoting apoptosis. Also disclosed are BCL-Xl inhibiting compositions and methods of promoting apoptosis in a mammal.

  N-苯甲酰芳基磺胺酰胺具有以下化学式，是BCL-Xl抑制剂，有助于促进细胞凋亡。还公开了BCL-Xl抑制组合物和在哺乳动物中促进细胞凋亡的方法。
• N-Acylsulfonamide apoptosis promoters
  申请人：——

  公开号：US20020086887A1

  公开（公告）日：2002-07-04

  N-Benzoyl arylsulfonamides having the formula 1 Are BCL-X1 inhibitors and are useful for promoting apoptosis. Also disclosed are BCL-X1 inhibiting compositions and methods of promoting apoptosis in a mammal.

  N-苯甲酰芳基磺胺酰胺具有以下化学式，是BCL-X1抑制剂，有助于促进细胞凋亡。还公开了BCL-X1抑制组合物和在哺乳动物中促进细胞凋亡的方法。