(2S)-1-[3-(3-chloro-phenyl)-2-oxo-propionyl]-pyrrolidine-2-carboxylic acid [2-(1H-indol-3-yl)-ethyl]-amide | 850543-71-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2S)-1-[3-(3-chloro-phenyl)-2-oxo-propionyl]-pyrrolidine-2-carboxylic acid [2-(1H-indol-3-yl)-ethyl]-amide
• CAS: 850543-71-4
• 化学式: C₂₄H₂₄ClN₃O₃
• 分子量: 437.926
• InChiKey: LQPQGLZKCUYIPR-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  82.27
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S)-1-[3-(3-chloro-phenyl)-2-oxo-propionyl]-pyrrolidine-2-carboxylic acid [2-(1H-indol-3-yl)-ethyl]-amide 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 以41%的产率得到(3S,12bS)-12b-(3-chloro-benzyl)-2,3,6,7,12,12b-hexahydropyrrolo-pyrazino[1',2':1,2]pyrido[3,4-b]indole-1,4-dione
  参考文献：
  名称：

  Diastereodivergent synthesis of 2,5-diketopiperazine derivatives of β-carboline and isoquinoline from l-amino acids

  摘要：

  Mild Pictet-Spengler-type condensation was applied to the synthesis of several tetrahydro-beta-carboline and tetrahydroisoquinoline derivatives. L-Amino acids were promoters of 1,4-chirality transfer with up to 100% de. The stereochemistry of the final diketopiperazines strongly depended on the structure of the L-amino acids used: acyclic amino acids gave predominantly the (R)configuration at the newly created stereogenic centre, whereas L-proline afforded the opposite configuration, as established by Xray crystallography. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.009
• 作为产物：
  描述：

  (2S)-{1-[2-(1H-indol-3-yl)-ethyl-carbamoyl]-ethyl}-methyl-carbamic acid benzyl ester 在 palladium on activated charcoal 盐酸 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (2S)-1-[3-(3-chloro-phenyl)-2-oxo-propionyl]-pyrrolidine-2-carboxylic acid [2-(1H-indol-3-yl)-ethyl]-amide
  参考文献：
  名称：

  Diastereodivergent synthesis of 2,5-diketopiperazine derivatives of β-carboline and isoquinoline from l-amino acids

  摘要：

  Mild Pictet-Spengler-type condensation was applied to the synthesis of several tetrahydro-beta-carboline and tetrahydroisoquinoline derivatives. L-Amino acids were promoters of 1,4-chirality transfer with up to 100% de. The stereochemistry of the final diketopiperazines strongly depended on the structure of the L-amino acids used: acyclic amino acids gave predominantly the (R)configuration at the newly created stereogenic centre, whereas L-proline afforded the opposite configuration, as established by Xray crystallography. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.009

文献信息

• Diastereoselective synthesis of some β-carboline derivatives from l-amino acids
  作者：Aleksandra Siwicka、Krystyna Wojtasiewicz、Andrzej Leniewski、Jan K. Maurin、Zbigniew Czarnocki

  DOI：10.1016/s0957-4166(02)00644-4

  日期：2002.10

  L-Ala and L-Val were used as chiral inductors in a series of reactions in which a Pictet-Spengler cyclization, completed under mild conditions was the key step. Diketopiperazine 7a and 8a having R configuration at the newly created stereogenic center were obtained with good diastereoselectivity due to 1,4-chirality transfer. Surprisingly, L-Pro promoted the formation of the product with S configuration in the predominant diastereomers 9a and 10a. (C) 2002 Published by Elsevier Science Ltd.