(1R,2R,3S)-2-methyl-1-[(1S,4R)-2-oxobornane-10-sulfanyl]-1-phenyl-3-heptanol | 853760-00-6

• 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: (1R,2R,3S)-2-methyl-1-[(1S,4R)-2-oxobornane-10-sulfanyl]-1-phenyl-3-heptanol
• 英文别名: (1S,4R)-1-[[(1R,2R,3S)-3-hydroxy-2-methyl-1-phenylheptyl]sulfanylmethyl]-7,7-dimethylbicyclo[2.2.1]heptan-2-one
• CAS: 853760-00-6
• 化学式: C₂₄H₃₆O₂S
• 分子量: 388.615
• InChiKey: MOORPUDFOGRRDH-LKRBNKJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S)-2-methyl-1-[(1S,4R)-2-oxobornane-10-sulfanyl]-1-phenyl-3-heptanol 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 25.5h， 生成 (4R,5R)-5-丁基-4-甲基二氢呋喃-2(3H)-酮
  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：

  (1S,2R,4R)-(-)-10-mercaptoisoboneol 、 (E)-2-Methyl-1-phenyl-hept-1-en-3-one 在 Me₂AlCl₃ 作用下， 以 二氯甲烷 为溶剂， 生成 (1R,2R,3S)-2-methyl-1-[(1S,4R)-2-oxobornane-10-sulfanyl]-1-phenyl-3-heptanol 、 (1R,2S,3S)-2-methyl-1-[(1S,4R)-2-oxobornane-10-sulfanyl]-1-phenyl-3-heptanol
  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.