(1'S,2'R,3'S,4'R,4a'S,8'S,8a'R)-3-<3',4'-dihydroxy-2'-methyl-8'-<(S)-2-methylbutanoyloxy>decahydronaphthalen-1'-yl>propyl pivalate | 161358-33-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (1'S,2'R,3'S,4'R,4a'S,8'S,8a'R)-3-<3',4'-dihydroxy-2'-methyl-8'-<(S)-2-methylbutanoyloxy>decahydronaphthalen-1'-yl>propyl pivalate
• 英文别名: [(1S,4aS,5R,6S,7R,8S,8aR)-8-[3-(2,2-dimethylpropanoyloxy)propyl]-5,6-dihydroxy-7-methyl-1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-1-yl] (2S)-2-methylbutanoate
• CAS: 161358-33-4
• 化学式: C₂₄H₄₂O₆
• 分子量: 426.594
• InChiKey: FJXZCIAIFKXXJR-JEJVXMLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 (1'S,2'R,3'S,4'R,4a'S,8'S,8a'R)-3-<3',4'-dihydroxy-2'-methyl-8'-<(S)-2-methylbutanoyloxy>decahydronaphthalen-1'-yl>propyl pivalate 在 吡啶 、 4-dimethylpyridine 作用下， 以71%的产率得到(1'S,2'R,3'S,4'R,4a'S,8'S,8a'R)-3-<3',4'-dibenzyloxy-2'-methyl-8'-<(S)-2-methylbutanoyloxy>decahydronaphthalen-1'-yl>propyl pivalate
  参考文献：
  名称：

  Total synthesis of (+)-dihydrocompactin

  摘要：

  The total synthesis of (+)-dihydrocompactin 1 has been achieved by employing double Michael reaction of 3-(tert-butyldimethylsiloxy)-1-acetylcyclohexene 13 with methyl crotonate and the TiCl4-promoted aldol condensation of the bis(trimethylsilyl enol ether) of methyl acetoacetate 7 as key reactions.

  DOI：

  10.1039/p19940002417
• 作为产物：
  描述：

  (1S,4aR,7S,8S,8aS)-8-(3'-hydroxypropyl)-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (S)-2-methylbutanoate 在 吡啶 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 叔丁醇 为溶剂， 反应 0.33h， 生成 (1'S,2'R,3'S,4'R,4a'S,8'S,8a'R)-3-<3',4'-dihydroxy-2'-methyl-8'-<(S)-2-methylbutanoyloxy>decahydronaphthalen-1'-yl>propyl pivalate
  参考文献：
  名称：

  Total synthesis of (+)-dihydrocompactin

  摘要：

  The total synthesis of (+)-dihydrocompactin 1 has been achieved by employing double Michael reaction of 3-(tert-butyldimethylsiloxy)-1-acetylcyclohexene 13 with methyl crotonate and the TiCl4-promoted aldol condensation of the bis(trimethylsilyl enol ether) of methyl acetoacetate 7 as key reactions.

  DOI：

  10.1039/p19940002417