(1S,4R)-1-[(1R,2R)-2-((R)-Hydroxy-phenyl-methyl)-1-(4-methoxy-phenyl)-butylsulfanylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one | 627875-80-3

• 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)-2-((R)-Hydroxy-phenyl-methyl)-1-(4-methoxy-phenyl)-butylsulfanylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one
• 英文别名: (1S,4R)-1-[[(1R,2R)-2-[(R)-hydroxy(phenyl)methyl]-1-(4-methoxyphenyl)butyl]sulfanylmethyl]-7,7-dimethylbicyclo[2.2.1]heptan-2-one
• CAS: 627875-80-3
• 化学式: C₂₈H₃₆O₃S
• 分子量: 452.658
• InChiKey: TXIQFHMYPXSWQQ-MPPIKMIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,4R)-1-[(1R,2R)-2-((R)-Hydroxy-phenyl-methyl)-1-(4-methoxy-phenyl)-butylsulfanylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one 在 sodium hypophosphite 、 Raney Ni W-2 作用下， 以 乙醇 、 acetate buffer 为溶剂， 反应 0.5h， 生成 (1R,2S)-2-(4-Methoxy-benzyl)-1-phenyl-butan-1-ol
  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：

  2-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-1-phenyl-butan-1-one 、 (1S,2R,4R)-(-)-10-mercaptoisoboneol 在 Me₂AlCl₃ 作用下， 以 二氯甲烷 为溶剂， 生成 (1S,4R)-1-[(1R,2R)-2-((R)-Hydroxy-phenyl-methyl)-1-(4-methoxy-phenyl)-butylsulfanylmethyl]-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one 、 (1S,4R)-1-[(1R,2S)-2-((R)-Hydroxy-phenyl-methyl)-1-(4-methoxy-phenyl)-butylsulfanylmethyl]-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