3-[2-[(1R,2S,4aR,8aS)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-2H-furan-5-one

• 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: 3-[2-[(1R,2S,4aR,8aS)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-2H-furan-5-one
• 化学式: C₂₀H₃₀O₂
• 分子量: 302.457
• InChiKey: XFPZMCXVOVGVEC-MFHCWRBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[2-[(1R,2S,4aR,8aS)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-2H-furan-5-one 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以83%的产率得到(+)-(3R,4S,5R,8S,9R,10S)-3,4-epoxyclerod-13-en-15,16-olide
  参考文献：
  名称：

  Total synthesis of cis-clerodane diterpenoids: (–)-agelasine A and (+)-(3R,4S,5R,8S,9R,10S)-3,4-epoxyclerod-13-en-15,16-olide

  摘要：

  The preparation of the enantiomerically homogeneous bicyclic iodide 26 and its use as a key intermediate for the total syntheses of the cis-clerodane diterpenoids (-)-agelasine A 5 and (+)-(3R,4S,5R,8S,9R,10S)-3,4-epoxyclerod-13-en-15,16-olide 6 are described.

  DOI：

  10.1039/p19950000963
• 作为产物：
  描述：

  4-溴-2(5h)-呋喃酮 、 (3S,4R,4aS,8aR)-4-(2-iodoethyl)-3,4,8,8a-tetramethyl-1,2,3,4a,5,6-hexahydronaphthalene 在 tris-(dibenzylideneacetone)dipalladium(0) 三苯胂 、 叔丁基锂 、 zinc dibromide 作用下， 生成 3-[2-[(1R,2S,4aR,8aS)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-2H-furan-5-one
  参考文献：
  名称：

  Total synthesis of cis-clerodane diterpenoids: (–)-agelasine A and (+)-(3R,4S,5R,8S,9R,10S)-3,4-epoxyclerod-13-en-15,16-olide

  摘要：

  The preparation of the enantiomerically homogeneous bicyclic iodide 26 and its use as a key intermediate for the total syntheses of the cis-clerodane diterpenoids (-)-agelasine A 5 and (+)-(3R,4S,5R,8S,9R,10S)-3,4-epoxyclerod-13-en-15,16-olide 6 are described.

  DOI：

  10.1039/p19950000963

文献信息

• Total synthesis of cis-clerodane diterpenoids: (–)-agelasine A and (+)-(3R,4S,5R,8S,9R,10S)-3,4-epoxyclerod-13-en-15,16-olide
  作者：Edward Piers、M. Livain Breau、Yongxin Han、Guy L. Plourde、Wen-Lung Yeh

  DOI：10.1039/p19950000963

  日期：——

  The preparation of the enantiomerically homogeneous bicyclic iodide 26 and its use as a key intermediate for the total syntheses of the cis-clerodane diterpenoids (-)-agelasine A 5 and (+)-(3R,4S,5R,8S,9R,10S)-3,4-epoxyclerod-13-en-15,16-olide 6 are described.