(2S)-2-[(3-benzo[1,3]dioxol-5-yl-2-oxo-propionyl)-methyl-amino]-N-[2-(1H-indol-3-yl)-ethyl]-3-methyl-butyramide | 850543-65-6

• 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)-2-[(3-benzo[1,3]dioxol-5-yl-2-oxo-propionyl)-methyl-amino]-N-[2-(1H-indol-3-yl)-ethyl]-3-methyl-butyramide
• CAS: 850543-65-6
• 化学式: C₂₆H₂₉N₃O₅
• 分子量: 463.533
• InChiKey: YPYRGZDNYMOQOO-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  100.73
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(3-benzo[1,3]dioxol-5-yl-2-oxo-propionyl)-methyl-amino]-N-[2-(1H-indol-3-yl)-ethyl]-3-methyl-butyramide 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 生成 (3S,12bR)-12b-benzo[1,3]dioxol-5-ylmethyl-3-isopropyl-2-methyl-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：

  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：

  色胺 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， 反应 2.0h， 生成 (2S)-2-[(3-benzo[1,3]dioxol-5-yl-2-oxo-propionyl)-methyl-amino]-N-[2-(1H-indol-3-yl)-ethyl]-3-methyl-butyramide
  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