(2S)-{1-[2-(1H-indol-3-yl)-ethyl-carbamoyl]-ethyl}-methyl-carbamic acid benzyl ester | 850543-60-1

• 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: (2S)-{1-[2-(1H-indol-3-yl)-ethyl-carbamoyl]-ethyl}-methyl-carbamic acid benzyl ester
• CAS: 850543-60-1
• 化学式: C₂₂H₂₅N₃O₃
• 分子量: 379.459
• InChiKey: DTJDUADWIUXBCN-INIZCTEOSA-N

物化性质

• 沸点：
  635.5±55.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  74.43
• 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-[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 作用下， 以 乙酸乙酯 为溶剂， 生成 (3S,12bR)-12b-benzyl-2,3-dimethyl-2,3,6,7,12,12b-hexahydro-pyrazino[1',2':1,2]pyrido[3,4-b]indole-1,4-dione
  参考文献：
  名称：

  Diastereoselective synthesis of some β-carboline derivatives from l-amino acids

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(02)00644-4
• 作为产物：
  描述：

  色胺 、 (2S)-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)propanoic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 生成 (2S)-{1-[2-(1H-indol-3-yl)-ethyl-carbamoyl]-ethyl}-methyl-carbamic acid benzyl ester
  参考文献：
  名称：

  Diastereoselective synthesis of some β-carboline derivatives from l-amino acids

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(02)00644-4

文献信息

• Diastereodivergent synthesis of 2,5-diketopiperazine derivatives of β-carboline and isoquinoline from l-amino acids
  作者：Aleksandra Siwicka、Krystyna Wojtasiewicz、Beata Rosiek、Andrzej Leniewski、Jan K. Maurin、Zbigniew Czarnocki

  DOI：10.1016/j.tetasy.2005.01.009

  日期：2005.3

  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.