(-)-pinan-3(R)-thiol | 157488-70-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-pinan-3(R)-thiol
• 英文别名: (1S,2S,,3R)-3-pinanethiol；(1S,2S,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptane-3-thiol
• CAS: 157488-70-5
• 化学式: C₁₀H₁₈S
• 分子量: 170.319
• InChiKey: BLTKIZZDFQAPPT-UYXSQOIJSA-N

物化性质

• 沸点：
  212.8±9.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (-)-pinan-3(R)-thiol 在 sodium ethanolate 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 18.67h， 生成 (+)-(1S,2S,R_S,1'R,2'S,3'R)-trans-2-pinanylsulfinylcyclohexanol
  参考文献：
  名称：

  The cleavage of meso-epoxides with homochiral thiols: synthesis of (+)- and (−)-trans-1-mercaptocyclohexan-2-ol

  摘要：

  The synthesis of (+)- and (-)-trans-1-mercaptocyclohexan-2-ol is described. Ring opening of cyclohexene oxide with (-)-4-methoxybenzylnopan-3(R)-thiol 1a followed by oxidation gives two readily separable diastereomeric sulfoxides. These sulfoxides display very different thermal stability but both undergo regio-specific syn-elimination to give cyclohexan-1-ol-2-sulfenic acid that can be reacted in situ with 3,5-dimethylthiophenol to give a mixed disulfide. Reduction of these disulfides with lithium aluminium hydride gives the title compounds in enantiomerically pure form. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00446-2
• 作为产物：
  描述：

  (1S,2S,3S,5R)-(+)-异松蒎醇 在 lithium aluminium tetrahydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醚 、 甲苯 为溶剂， 生成 (-)-pinan-3(R)-thiol
  参考文献：
  名称：

  The cleavage of meso-epoxides with homochiral thiols: synthesis of (+)- and (−)-trans-1-mercaptocyclohexan-2-ol

  摘要：

  The synthesis of (+)- and (-)-trans-1-mercaptocyclohexan-2-ol is described. Ring opening of cyclohexene oxide with (-)-4-methoxybenzylnopan-3(R)-thiol 1a followed by oxidation gives two readily separable diastereomeric sulfoxides. These sulfoxides display very different thermal stability but both undergo regio-specific syn-elimination to give cyclohexan-1-ol-2-sulfenic acid that can be reacted in situ with 3,5-dimethylthiophenol to give a mixed disulfide. Reduction of these disulfides with lithium aluminium hydride gives the title compounds in enantiomerically pure form. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00446-2

文献信息

• Asymmetric epoxidation using chiral sulfur ylides
  作者：Varinder K. Aggarwal、Marilena Kalomiri、Andrew P. Thomas

  DOI：10.1016/0957-4166(94)80035-9

  日期：1994.4

  Novel chiral sulfides, derived from pinene, have been prepared, converted to sulfonium salts and treated with base and aldehydes to generate non-racemic epoxides. Low to moderate enantioselectivities were obtained in the product epoxides and this possibly occurred as a result of using diastereomeric mixtures of sulfonium salts. Dibenzyl substituted sulfonium salts were also prepared to avoid formation of diastereomers but upon treatment with base and an aldehyde this gave the Stevens rearrangement product instead of epoxide.
• The cleavage of meso-epoxides with homochiral thiols: synthesis of (+)- and (−)-trans-1-mercaptocyclohexan-2-ol
  作者：Harry Adams、Richard Bell、Yiu-Yin Cheung、D.Neville Jones、Nicholas C.O. Tomkinson

  DOI：10.1016/s0957-4166(99)00446-2

  日期：1999.10

  The synthesis of (+)- and (-)-trans-1-mercaptocyclohexan-2-ol is described. Ring opening of cyclohexene oxide with (-)-4-methoxybenzylnopan-3(R)-thiol 1a followed by oxidation gives two readily separable diastereomeric sulfoxides. These sulfoxides display very different thermal stability but both undergo regio-specific syn-elimination to give cyclohexan-1-ol-2-sulfenic acid that can be reacted in situ with 3,5-dimethylthiophenol to give a mixed disulfide. Reduction of these disulfides with lithium aluminium hydride gives the title compounds in enantiomerically pure form. (C) 1999 Elsevier Science Ltd. All rights reserved.