[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (3R,3'S)-5-methoxy-1'-methyl-2-oxospiro[1H-indole-3,4'-pyrrolidine]-3'-carboxylate | 174692-90-1

• 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,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (3R,3'S)-5-methoxy-1'-methyl-2-oxospiro[1H-indole-3,4'-pyrrolidine]-3'-carboxylate
• CAS: 174692-90-1
• 化学式: C₂₄H₃₄N₂O₄
• 分子量: 414.545
• InChiKey: YNYAOAJKXIHURO-OMZMLLDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (3R,3'S)-5-methoxy-1'-methyl-2-oxospiro[1H-indole-3,4'-pyrrolidine]-3'-carboxylate 在 氢氧化钾 、 3-羟基-4-甲基-2(3H)-噻唑硫酮 、 18-冠醚-6 、 偶氮二异丁腈 、 三正丁基氢锡 、 4-吡咯烷基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 (-)-horsfiline
  参考文献：
  名称：

  Oxindole alkaloids. A novel non-biomimetic entry to (−)-Horsfiline.

  摘要：

  A novel non-biomimetic synthesis of horsfiline has been developed. The key pyrrolidine forming reaction is the 1,3-dipolar cycloaddition of the thermally generated N-methylazomethine ylide to a suitable 3-alkylidene-indolin-2(3H)one. The same strategy was also applied to the synthesis of pure (R)-(-)-enantiomer.

  DOI：

  10.1016/0957-4166(95)00406-8
• 作为产物：
  描述：

  5-甲氧基靛红 在 3 A molecular sieve 作用下， 以 二乙二醇二甲醚 、 甲苯 为溶剂， 反应 2.0h， 生成 [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (3R,3'S)-5-methoxy-1'-methyl-2-oxospiro[1H-indole-3,4'-pyrrolidine]-3'-carboxylate
  参考文献：
  名称：

  Oxindole alkaloids. A novel non-biomimetic entry to (−)-Horsfiline.

  摘要：

  A novel non-biomimetic synthesis of horsfiline has been developed. The key pyrrolidine forming reaction is the 1,3-dipolar cycloaddition of the thermally generated N-methylazomethine ylide to a suitable 3-alkylidene-indolin-2(3H)one. The same strategy was also applied to the synthesis of pure (R)-(-)-enantiomer.

  DOI：

  10.1016/0957-4166(95)00406-8

文献信息

• Oxindole alkaloids. A novel non-biomimetic entry to (−)-Horsfiline.
  作者：Giovanni Palmisano、Rita Annunziata、Gianluca Papeo、Massimo Sisti

  DOI：10.1016/0957-4166(95)00406-8

  日期：1996.1

  A novel non-biomimetic synthesis of horsfiline has been developed. The key pyrrolidine forming reaction is the 1,3-dipolar cycloaddition of the thermally generated N-methylazomethine ylide to a suitable 3-alkylidene-indolin-2(3H)one. The same strategy was also applied to the synthesis of pure (R)-(-)-enantiomer.