(1R,2R)-2-(phenylthio)cyclooctan-1-ol | 68771-08-4

• 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)cyclooctan-1-ol
• 英文别名: (1R,2R)-2-phenylsulfanylcyclooctan-1-ol
• CAS: 68771-08-4
• 化学式: C₁₄H₂₀OS
• 分子量: 236.378
• InChiKey: DMOKYJFVYFADOO-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  苯甲酰氯 、 (1S,2S)-2-phenylsulfanylcyclooctan-1-ol 在 三乙胺 、 (S)-1-methyl-2-[(dihydroisoindol-2-yl)methyl]pyrrolidine 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以49%的产率得到C₂₁H₂₄O₂S
  参考文献：
  名称：

  Efficient and Enantioselective Kinetic Resolution of Cyclic β-Hydroxy Sulfides by Chiral 1,2-Diamine Catalyzed Asymmetric Acylation

  摘要：

  通过在手性1,2-二胺（用量为0.1 mol %）和三乙胺的存在下，环状β-羟基硫醇与苯甲酰氯反应，实现了环状β-羟基硫醇的动力学拆分。该反应能够以优异的立体选择性得到相应的苯甲酸盐和未反应的醇。

  DOI：

  10.1246/cl.2010.382

文献信息

• 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.
• Efficient and Enantioselective Kinetic Resolution of Cyclic β-Hydroxy Sulfides by Chiral 1,2-Diamine Catalyzed Asymmetric Acylation
  作者：Yoshiyuki Kawamata、Takeshi Oriyama

  DOI：10.1246/cl.2010.382

  日期：2010.4.5

  Kinetic resolution of cyclic β-hydroxy sulfides has been achieved by reaction with benzoyl chloride in the presence of a catalytic amount (0.1 mol %) of a chiral 1,2-diamine combined with triethylamine. This reaction affords the corresponding benzoates and unreacted alcohols with excellent enantioselectivities.

  通过在手性1,2-二胺（用量为0.1 mol %）和三乙胺的存在下，环状β-羟基硫醇与苯甲酰氯反应，实现了环状β-羟基硫醇的动力学拆分。该反应能够以优异的立体选择性得到相应的苯甲酸盐和未反应的醇。