(1R,2R)-2-phenylthio-1-cyclopentanol | 1200400-54-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (1R,2R)-2-phenylthio-1-cyclopentanol
• 英文别名: (1R,2R)-2-(phenylsulfanyl)cyclopentan-1-ol；(1R,2R)-2-phenylsulfanylcyclopentan-1-ol
• CAS: 1200400-54-9
• 化学式: C₁₁H₁₄OS
• 分子量: 194.298
• InChiKey: JIAWDQCLDCXYTK-GHMZBOCLSA-N

物化性质

• 沸点：
  329.9±35.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2-环氧环戊烷 以65%的产率得到
  参考文献：
  名称：

  Maiti A. K., Bhattacharyya P., Tetrahedron, 50 (1994) N 35, S 10483-10490

  摘要：

  DOI：

文献信息

• Salan-Vanadium Catalyzed Enantioselective Desymmetrization of meso-Epoxides with Aromatic Thiols
  作者：Jiangtao Sun、Weijin Gu、Yijun Huang、Xu Pan、Chengjian Zhu

  DOI：10.2174/157017809788489990

  日期：2009.6.1

  The first example of salan-vanadium catalyzed enantioselective ring-opening of meso-epoxides has been reported, which furnished β-hydroxy sulfides in good yields and moderate enantioselectivities.

  首次报道了以salan-钒为催化剂的手性选择性开环反应，该反应能够高效地生成β-羟基硫化物，并具有适度的对映选择性。
• Enantioselective ring-opening reaction of meso-epoxides with ArSH catalyzed by heterobimetallic Ti–Ga–Salen system
  作者：Jiangtao Sun、Fang Yuan、Minghua Yang、Yi Pan、Chengjian Zhu

  DOI：10.1016/j.tetlet.2008.11.060

  日期：2009.2

  The enantioselective ring-opening reaction of meso-epoxides with aryl thiols catalyzed by a chiral heterobimetallic Ti–Ga–Salen complex was realized, and the 1,2-mercapto alcohols were obtained in good yields and moderate to high enantioselectivities (up to 92% ee). A strong synergistic cooperation between different Lewis acids in the system was exhibited in the catalytic process.

  的对映选择性开环反应的内消旋环氧化物与芳基硫醇催化由手性异核的Ti-Ga的Salen配复合物实现，该1,2-二巯基醇以良好产率获得和中到高对映选择性（高达92％ ee）。在催化过程中，体系中的不同路易斯酸之间表现出强烈的协同作用。
• Catalytic Asymmetric Ring-Opening Reaction of<i>meso</i>-Epoxides with Aryl Selenols and Thiols Catalyzed by a Heterobimetallic Gallium-Titanium-Salen Complex
  作者：Jiangtao Sun、Minghua Yang、Fang Yuan、Xuefeng Jia、Xia Yang、Yi Pan、Chengjian Zhu

  DOI：10.1002/adsc.200800767

  日期：2009.4

  Abstractmagnified imageA chiral heterobimetallic Lewis acid complex has been developed as an efficient catalyst. The enantioselective desymmetrization of meso‐epoxides with aryl selenols and thiols catalyzed by the heterobimetallic complex has been optimized. The optically active β‐arylseleno alcohols and β‐hydroxy sulfides were obtained in good yields and high enantioselectivities (up to 97% ee and 92% ee, respectively). A strong synergistic effect between different Lewis acids was exhibited in the catalytic process.
• Lithium BINOL Phosphate Catalyzed Desymmetrization of <i>meso</i>-Epoxides with Aromatic Thiols
  作者：Gajendrasingh Ingle、Michael G. Mormino、Jon C. Antilla

  DOI：10.1021/ol502527q

  日期：2014.11.7

  A highly enantioselective method for desymmetrization of meso-epoxides using thiols is reported. This is the first example of epoxide activation achieved using metal BINOL phosphates. The reaction has a broad scope in terms of epoxide substrates and aromatic thiol nucleophiles. The resulting beta-hydroxyl sulfides are obtained in excellent yield and enantioselectivity.
• COHEN, T.;RITTER, R. H.;OUELLETTE, D., J. AMER. CHEM. SOC., 1982, 104, N 25, 7142-7148
  作者：COHEN, T.、RITTER, R. H.、OUELLETTE, D.

  DOI：——

  日期：——