N-(2-chloro-3-methylbutanoyl)tryptophan methyl ester | 141734-85-2

• 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: N-(2-chloro-3-methylbutanoyl)tryptophan methyl ester
• 英文别名: methyl (2S)-2-[(2-chloro-3-methylbutanoyl)amino]-3-(1H-indol-3-yl)propanoate
• CAS: 141734-85-2；141734-93-2
• 化学式: C₁₇H₂₁ClN₂O₃
• 分子量: 336.818
• InChiKey: AOJXYEYCIVNEHL-MLCCFXAWSA-N

物化性质

• 沸点：
  543.7±50.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  71.19
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(2-chloro-3-methylbutanoyl)tryptophan methyl ester 在 乙腈 作用下， 反应 1.0h， 以17%的产率得到methyl 1,2,3,4,5,6-hexahydro-5-isopropyl-4-oxoazepino<4,5-b>indole-2-carboxylate
  参考文献：
  名称：

  Synthesis of (–)-indolactam V

  摘要：

  A stereospecific 7-step synthesis of (-)-indolactam V1 from tryptophan methyl ester is described. The key steps are the photocyclisation of the dichloroamide 6 to give the isomeric 7-hydroxy-7-isopropyl-pyrrolo[4,3,2-fg][3]benzazocines 16 + 18 and the nitrene-mediated ring expansion of the derived azide 5 to give the 9-membered imine 4. The synthesis is completed by stereoselective reduction of the imine bond and N-methylation.

  DOI：

  10.1039/p19920000823
• 作为产物：
  描述：

  2-氯-3-甲基丁酰氯 在 sodium hydroxide 、 乙醚 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 N-(2-chloro-3-methylbutanoyl)tryptophan methyl ester
  参考文献：
  名称：

  Synthesis of (–)-indolactam V

  摘要：

  A stereospecific 7-step synthesis of (-)-indolactam V1 from tryptophan methyl ester is described. The key steps are the photocyclisation of the dichloroamide 6 to give the isomeric 7-hydroxy-7-isopropyl-pyrrolo[4,3,2-fg][3]benzazocines 16 + 18 and the nitrene-mediated ring expansion of the derived azide 5 to give the 9-membered imine 4. The synthesis is completed by stereoselective reduction of the imine bond and N-methylation.

  DOI：

  10.1039/p19920000823

文献信息

• Synthesis of (–)-indolactam V
  作者：Mark Mascal、Christopher J. Moody、Alexandra M. Z. Slawin、David J. Williams

  DOI：10.1039/p19920000823

  日期：——

  A stereospecific 7-step synthesis of (-)-indolactam V1 from tryptophan methyl ester is described. The key steps are the photocyclisation of the dichloroamide 6 to give the isomeric 7-hydroxy-7-isopropyl-pyrrolo[4,3,2-fg][3]benzazocines 16 + 18 and the nitrene-mediated ring expansion of the derived azide 5 to give the 9-membered imine 4. The synthesis is completed by stereoselective reduction of the imine bond and N-methylation.