(8aS,13aR)-13a-methyl-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 | 850543-99-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (8aS,13aR)-13a-methyl-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
• CAS: 850543-99-6
• 化学式: C₁₈H₂₂N₂O₄
• 分子量: 330.384
• InChiKey: GPXBNVDJNVGRIE-SCLBCKFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  59.08
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (8aS,13aR)-13a-methyl-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 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 (7aR,11aR)-2,3-Dimethoxy-11a-methyl-5,7a,8,9,10,11a-hexahydro-6H-6a,10a-diaza-cyclopenta[b]phenanthrene-7,11-dione
  参考文献：
  名称：

  The structure of some trans-diketopiperazine derivatives of isoquinoline and β-carboline

  摘要：

  The study on the absolute stereochemistry of trans-diketopiperazine 3a was performed by a crystallographic method. This result supports our previous assignments concerning the diverse chiral induction in the Pictet-Spengler condensation from L-amino acids. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.015
• 作为产物：
  描述：

  (2S)-N-[2-(3,4-dimethoxyphenyl)ethyl]pyrrolidine-2-carboxamide 在 盐酸 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (8aS,13aR)-13a-methyl-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