(1R,2R,3R)-1-(4-chlorophenyl)-3-(4-methoxyphenyl)-2-methyl-3-[(1S,4R)-2-oxobornane-10-sulfanyl]-1-propanol | 853759-99-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (1R,2R,3R)-1-(4-chlorophenyl)-3-(4-methoxyphenyl)-2-methyl-3-[(1S,4R)-2-oxobornane-10-sulfanyl]-1-propanol
• CAS: 853759-99-6
• 化学式: C₂₇H₃₃ClO₃S
• 分子量: 473.076
• InChiKey: IDBQLFNKNCTOBZ-UYQBGJIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.89
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R)-1-(4-chlorophenyl)-3-(4-methoxyphenyl)-2-methyl-3-[(1S,4R)-2-oxobornane-10-sulfanyl]-1-propanol 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)-1-(4-Chloro-phenyl)-3-(4-methoxy-phenyl)-2-methyl-propan-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：

  (E)-1-(4-Chloro-phenyl)-3-(4-methoxy-phenyl)-2-methyl-propenone 、 (1S,2R,4R)-(-)-10-mercaptoisoboneol 在 Me₂AlCl₃ 作用下， 以 二氯甲烷 为溶剂， 生成 (1R,2R,3R)-1-(4-chlorophenyl)-3-(4-methoxyphenyl)-2-methyl-3-[(1S,4R)-2-oxobornane-10-sulfanyl]-1-propanol 、 (1R,2S,3R)-1-(4-chlorophenyl)-3-(4-methoxyphenyl)-2-methyl-3-[(1S,4R)-2-oxobornane-10-sulfanyl]-1-propanol
  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

• 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
  作者：Minoru Ozeki、Daisuke Hashimoto、Kiyoharu Nishide、Tetsuya Kajimoto、Manabu Node

  DOI：10.1016/j.tetasy.2005.03.017

  日期：2005.5

  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.