trimethyl (2S,3aR,8bR)-8b-phenylselanyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-2,3,4-tricarboxylate | 245755-95-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trimethyl (2S,3aR,8bR)-8b-phenylselanyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-2,3,4-tricarboxylate
• CAS: 245755-95-7
• 化学式: C₂₂H₂₂N₂O₆Se
• 分子量: 489.386
• InChiKey: BLHRIRVCNWQWAX-LQBOVUBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  trimethyl (2S,3aR,8bR)-8b-phenylselanyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-2,3,4-tricarboxylate 在 偶氮二异丁腈 、 二苯基二硒醚 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以90%的产率得到(2S,3aS,8aR)-2,3,3a,8a-Tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid trimethyl ester
  参考文献：
  名称：

  On the Reaction of Tryptophan Derivatives with N-Phenylselenyl Phthalimide:  The Nature of the Kinetic and Thermodynamic Hexahydropyrrolo[2,3-b]indole Products. Alkylation of Tryptophan with Inversion of Configuration

  摘要：

  The cyclization of a range of tryptophan derivatives with N-phenylselenyl phthalimide leading to 3a-phenylselenyl-1,2,3,3a,8,8a-hexahydro[2,3b]pyrroloindoles has been studied. It is established that in each case the kinetic diastereomer has the C-2 substituent on the exo face of the diazabicyclo[3.3.0]octane skeleton, whereas the thermodynamic isomers have the C-2 substituent endo. A simple protocol for the alkylation of tryptophan, leading to alpha-substituted tryptophans with clean inversion of configuration, is presented.

  DOI：

  10.1021/jo991093+
• 作为产物：
  描述：

  N-(苯硒基)邻苯二甲酰亚胺 、 methyl 3-[(2S)-3-methoxy-2-(methoxycarbonylamino)-3-oxopropyl]indole-1-carboxylate 在 对甲苯磺酸 、 sodium sulfate 作用下， 以 二氯甲烷 为溶剂， 生成 trimethyl (2S,3aS,8bS)-8b-phenylselanyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-2,3,4-tricarboxylate 、 trimethyl (2S,3aR,8bR)-8b-phenylselanyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-2,3,4-tricarboxylate
  参考文献：
  名称：

  On the Reaction of Tryptophan Derivatives with N-Phenylselenyl Phthalimide:  The Nature of the Kinetic and Thermodynamic Hexahydropyrrolo[2,3-b]indole Products. Alkylation of Tryptophan with Inversion of Configuration

  摘要：

  The cyclization of a range of tryptophan derivatives with N-phenylselenyl phthalimide leading to 3a-phenylselenyl-1,2,3,3a,8,8a-hexahydro[2,3b]pyrroloindoles has been studied. It is established that in each case the kinetic diastereomer has the C-2 substituent on the exo face of the diazabicyclo[3.3.0]octane skeleton, whereas the thermodynamic isomers have the C-2 substituent endo. A simple protocol for the alkylation of tryptophan, leading to alpha-substituted tryptophans with clean inversion of configuration, is presented.

  DOI：

  10.1021/jo991093+

文献信息

• On the Reaction of Tryptophan Derivatives with <i>N</i>-Phenylselenyl Phthalimide:  The Nature of the Kinetic and Thermodynamic Hexahydropyrrolo[2,3-<i>b</i>]indole Products. Alkylation of Tryptophan with Inversion of Configuration
  作者：David Crich、Xianhai Huang

  DOI：10.1021/jo991093+

  日期：1999.9.1

  The cyclization of a range of tryptophan derivatives with N-phenylselenyl phthalimide leading to 3a-phenylselenyl-1,2,3,3a,8,8a-hexahydro[2,3b]pyrroloindoles has been studied. It is established that in each case the kinetic diastereomer has the C-2 substituent on the exo face of the diazabicyclo[3.3.0]octane skeleton, whereas the thermodynamic isomers have the C-2 substituent endo. A simple protocol for the alkylation of tryptophan, leading to alpha-substituted tryptophans with clean inversion of configuration, is presented.