(1S,4R)-1-((1R,2R,3S)-3-Cyclohexyl-3-hydroxy-2-methyl-1-phenyl-propylsulfanylmethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one | 627875-88-1

• 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: (1S,4R)-1-((1R,2R,3S)-3-Cyclohexyl-3-hydroxy-2-methyl-1-phenyl-propylsulfanylmethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one
• CAS: 627875-88-1
• 化学式: C₂₆H₃₈O₂S
• 分子量: 414.653
• InChiKey: OHUFOMGPPYBKQV-GYKZEHCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.43
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,4R)-1-((1R,2R,3S)-3-Cyclohexyl-3-hydroxy-2-methyl-1-phenyl-propylsulfanylmethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one 在 4-二甲氨基吡啶 、 ruthenium trichloride 、 sodium hydroxide 、 高碘酸 作用下， 以 吡啶 、 四氯化碳 、 水 、 乙腈 为溶剂， 反应 24.5h， 生成 (4S,5R)-5-cyclohexyl-4-methyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  A concise synthetic route to optically active cis-β,γ-disubstituted-γ-butyrolactones via tandem Michael–MPV reaction: new total synthesis of (−)-cis-whisky lactone and (−)-cis-cognac lactone

  摘要：

  Optically active cis-beta,gamma-disubstituted-gamma-butyrolactones, for example, cis-whisky lactone and cis-cognac lactone, were readily synthesized by using tandem Michael-Meerwein-Ponndorf-Verley reactions that employed (-)-10-mercapto-isoborneol as a chiral template in the key step. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.017
• 作为产物：
  描述：

  (E)-1-Cyclohexyl-2-methyl-3-phenyl-propenone 、 (1S,2R,4R)-(-)-10-mercaptoisoboneol 在 Me₂AlCl₃ 、 2,3,4,5,6-五氟苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以50%的产率得到(1S,4R)-1-((1R,2R,3S)-3-Cyclohexyl-3-hydroxy-2-methyl-1-phenyl-propylsulfanylmethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one
  参考文献：
  名称：

  A concise synthetic route to optically active cis-β,γ-disubstituted-γ-butyrolactones via tandem Michael–MPV reaction: new total synthesis of (−)-cis-whisky lactone and (−)-cis-cognac lactone

  摘要：

  Optically active cis-beta,gamma-disubstituted-gamma-butyrolactones, for example, cis-whisky lactone and cis-cognac lactone, were readily synthesized by using tandem Michael-Meerwein-Ponndorf-Verley reactions that employed (-)-10-mercapto-isoborneol as a chiral template in the key step. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.017

文献信息

• One-Step Stereocontrol of Three Contiguous Stereogenic Centers in Acyclic Systems: The Tuning Effect of an Additive in a Tandem Asymmetric Michael Addition and Meerwein–Ponndorf–Verley Reduction
  作者：Kiyoharu Nishide、Minoru Ozeki、Hideaki Kunishige、Yukihiro Shigeta、Pranab K. Patra、Yuri Hagimoto、Manabu Node

  DOI：10.1002/anie.200351915

  日期：2003.9.29