(3aS,8ar)-8-benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole | 799561-42-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (3aS,8ar)-8-benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole
• 英文别名: (3aR,8bS)-4-benzyl-3,8b-dimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indole
• CAS: 799561-42-5
• 化学式: C₁₉H₂₂N₂
• 分子量: 278.397
• InChiKey: VVOLDSIKYBYERY-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-methyl 2-(1-benzyl-3-methyl-2-oxoindolin-3-yl)ethylcarbamate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以43%的产率得到(3aS,8ar)-8-benzyl-1,3a-dimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole
  参考文献：
  名称：

  Synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed intramolecular cyanoamidation

  摘要：

  The cyanoamidation of olefins was achieved. When N-(2-vinylphenyl)cyanoformamides were treated with palladium catalyst, intramolecular cyanoamidation took place to give corresponding 3,3-disubstituted oxindoles. P(t-Bu)(3) showed a remarkable effect on this reaction. When it was used with Pd(dba)(2), the reaction was completed in 15 min at 100 degrees C for many substrates. Furthermore, the enantioselective cyanoamidation was accomplished with Pd(dba)(2) and an optically active phosphoramidite to provide optically active 3,3-disubstituted oxindoles. Manipulation of the resulting oxindoles has been studied. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.01.073

文献信息

• Enantioselective Synthesis of 3,3-Disubstituted Oxindoles through Pd-Catalyzed Cyanoamidation
  作者：Yoshizumi Yasui、Haruhi Kamisaki、Yoshiji Takemoto

  DOI：10.1021/ol801168j

  日期：2008.8.7

  The first enantioselective cyanoamidation of olefins provides quick access to a variety of 3,3-disubstituted oxindoles. The combination of Pd(dba)(2), an optically active phosphoramidite, and N,N-dimethylpropylene urea (DMPU) in decalin were found to be the best conditions.
• Synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed intramolecular cyanoamidation
  作者：Yoshizumi Yasui、Haruhi Kamisaki、Takayuki Ishida、Yoshiji Takemoto

  DOI：10.1016/j.tet.2010.01.073

  日期：2010.3

  The cyanoamidation of olefins was achieved. When N-(2-vinylphenyl)cyanoformamides were treated with palladium catalyst, intramolecular cyanoamidation took place to give corresponding 3,3-disubstituted oxindoles. P(t-Bu)(3) showed a remarkable effect on this reaction. When it was used with Pd(dba)(2), the reaction was completed in 15 min at 100 degrees C for many substrates. Furthermore, the enantioselective cyanoamidation was accomplished with Pd(dba)(2) and an optically active phosphoramidite to provide optically active 3,3-disubstituted oxindoles. Manipulation of the resulting oxindoles has been studied. (C) 2010 Elsevier Ltd. All rights reserved.