methyl (3aS,8bS)-8b-methyl-4-[(1S)-1-naphthalen-1-ylethyl]-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-3-carboxylate | 880647-70-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl (3aS,8bS)-8b-methyl-4-[(1S)-1-naphthalen-1-ylethyl]-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-3-carboxylate
• CAS: 880647-70-1
• 化学式: C₂₅H₂₆N₂O₂
• 分子量: 386.494
• InChiKey: KOHAMRDVSYMAOQ-YRSQORNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (3aS,8bS)-8b-methyl-4-[(1S)-1-naphthalen-1-ylethyl]-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-3-carboxylate 在 palladium dihydroxide 氢气 、 potassium carbonate 、 红铝 作用下， 以 甲苯 为溶剂， 生成 (3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole
  参考文献：
  名称：

  Diastereoselective Fischer-Type Pyrroloindole Synthesis and Its Application to the Synthesis of Chiral Pyrroloindole Alkaloids

  摘要：

  Facile access to optically active pyrroloindoles by Fischer-type pyrroloindole synthesis is investigated. The reaction using chiral hydrazines prepared from commercially available chiral amines proceeded with diastereoselective cyclization (up to 70% de), and a short-step conversion of the cycloadducts to (-)-desoxyeseroline and pyrroloindole alkaloids was achieved.

  DOI：

  10.3987/com-05-s(k)71
• 作为产物：
  描述：

  在 silica gel 、 sodium carbonate 作用下， 生成 methyl (3aS,8bS)-8b-methyl-4-[(1S)-1-naphthalen-1-ylethyl]-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-3-carboxylate
  参考文献：
  名称：

  Diastereoselective Fischer-Type Pyrroloindole Synthesis and Its Application to the Synthesis of Chiral Pyrroloindole Alkaloids

  摘要：

  Facile access to optically active pyrroloindoles by Fischer-type pyrroloindole synthesis is investigated. The reaction using chiral hydrazines prepared from commercially available chiral amines proceeded with diastereoselective cyclization (up to 70% de), and a short-step conversion of the cycloadducts to (-)-desoxyeseroline and pyrroloindole alkaloids was achieved.

  DOI：

  10.3987/com-05-s(k)71

文献信息

• Diastereoselective Fischer-Type Pyrroloindole Synthesis and Its Application to the Synthesis of Chiral Pyrroloindole Alkaloids
  作者：Atsushi Nishida、Satoru Ushigome、Ayako Sugimoto、Shigeru Arai

  DOI：10.3987/com-05-s(k)71

  日期：——

  Facile access to optically active pyrroloindoles by Fischer-type pyrroloindole synthesis is investigated. The reaction using chiral hydrazines prepared from commercially available chiral amines proceeded with diastereoselective cyclization (up to 70% de), and a short-step conversion of the cycloadducts to (-)-desoxyeseroline and pyrroloindole alkaloids was achieved.