(8aS)-3-benzo[1,3]dioxol-5-ylmethyl-2-[2-(3,4-dimethoxy-phenyl)-ethyl]-3-hydroxy-hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione | 850543-88-3

• 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: (8aS)-3-benzo[1,3]dioxol-5-ylmethyl-2-[2-(3,4-dimethoxy-phenyl)-ethyl]-3-hydroxy-hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione
• 英文别名: (8aS)-3-(1,3-benzodioxol-5-ylmethyl)-2-[2-(3,4-dimethoxyphenyl)ethyl]-3-hydroxy-6,7,8,8a-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione
• CAS: 850543-88-3
• 化学式: C₂₅H₂₈N₂O₇
• 分子量: 468.507
• InChiKey: PALHNQGINYNMCD-CPFIQGLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  97.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (8aS)-3-benzo[1,3]dioxol-5-ylmethyl-2-[2-(3,4-dimethoxy-phenyl)-ethyl]-3-hydroxy-hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione 在 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 以40%的产率得到(8aS,13aS)-13a-([1,3]dioxol-benzyl)-2,3-dimethoxy-5,8a,9,10,11,13a-hexahydro-8H-pyrrolo[1',2':4,5]pyrazino[2,1-a]isoquinoline-8,13(6H)-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：

  β-(benzo[1,3]dioxol-5-yl)pyruvic acid 、 (2S)-N-[2-(3,4-dimethoxyphenyl)ethyl]pyrrolidine-2-carboxamide 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (8aS)-3-benzo[1,3]dioxol-5-ylmethyl-2-[2-(3,4-dimethoxy-phenyl)-ethyl]-3-hydroxy-hexahydro-pyrrolo[1,2-a]pyrazine-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