(3R)-(4-methoxybenzyl)-nopan-3-thiol | 257950-73-5

• 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: (3R)-(4-methoxybenzyl)-nopan-3-thiol
• 英文别名: (1S,2S,3R,5R)-2-[2-[(4-methoxyphenyl)methoxy]ethyl]-6,6-dimethylbicyclo[3.1.1]heptane-3-thiol
• CAS: 257950-73-5
• 化学式: C₁₉H₂₈O₂S
• 分子量: 320.496
• InChiKey: OJXWAGZEZNEKRS-LAVFITLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  19.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R)-(4-methoxybenzyl)-nopan-3-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 3.66h， 生成 (-)-(1R,2R,S_S,1'R,2'S,3'R)-trans-2-(4-methoxybenzyl)-nopylsulfonylcyclohexanol
  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：

  (3R)-(4-methoxybenzyl)-nopan-3-N,N-dimethyldithiocarbamate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以85%的产率得到(3R)-(4-methoxybenzyl)-nopan-3-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

• 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.