Dimethyl 2-<3-<2-b,N^b-bis(phenylmethyl)amino>ethyl>indolyl>propanedioate | 153275-89-9

• 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: Dimethyl 2-<3-<2-b,N^b-bis(phenylmethyl)amino>ethyl>indolyl>propanedioate
• 英文别名: dimethyl 2-[3-[2-(dibenzylamino)ethyl]-1H-indol-2-yl]propanedioate
• CAS: 153275-89-9
• 化学式: C₂₉H₃₀N₂O₄
• 分子量: 470.568
• InChiKey: NWMMBZGYQOUCLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Dimethyl 2-<3-<2-b,N^b-bis(phenylmethyl)amino>ethyl>indolyl>propanedioate 在 三乙胺盐酸盐 、 lithium chloride 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 2.5h， 以84%的产率得到Methyl 3-<2-b,N^b-bis(phenylmethyl)amino>ethyl>indole-2-ethanoate
  参考文献：
  名称：

  Total synthesis of strychnan- and aspidospermatan-type alkaloids. 2. Generation of 15-(3-furanyl) ABCE tetracyclic intermediates

  摘要：

  The synthesis of N(b)-benzyl-2-(dimethyl 2-malonyl)- and 2-(methyl 2-acetyl)tryptamines (21, 25) provides access to methyl 4-(3-furanyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate (12) and methyl 3-benzyl-5-(3-furanyl)-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylate (9), potential intermediates for the syntheses of strychnos alkaloids. A new condensation-sigmatropic rearrangement reaction gives the tetracyclic product 9 directly from the tryptamine 25.

  DOI：

  10.1021/jo00078a029
• 作为产物：
  描述：

  Thallium dimethyl malonate 、 N,N-dibenzyl-2-(3-chloroindol-3-yl)ethanamine 以 四氢呋喃 为溶剂， 生成 Dimethyl 2-<3-<2-b,N^b-bis(phenylmethyl)amino>ethyl>indolyl>propanedioate
  参考文献：
  名称：

  Total synthesis of strychnan- and aspidospermatan-type alkaloids. 2. Generation of 15-(3-furanyl) ABCE tetracyclic intermediates

  摘要：

  The synthesis of N(b)-benzyl-2-(dimethyl 2-malonyl)- and 2-(methyl 2-acetyl)tryptamines (21, 25) provides access to methyl 4-(3-furanyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate (12) and methyl 3-benzyl-5-(3-furanyl)-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylate (9), potential intermediates for the syntheses of strychnos alkaloids. A new condensation-sigmatropic rearrangement reaction gives the tetracyclic product 9 directly from the tryptamine 25.

  DOI：

  10.1021/jo00078a029

文献信息

• Total synthesis of strychnan- and aspidospermatan-type alkaloids. 2. Generation of 15-(3-furanyl) ABCE tetracyclic intermediates
  作者：Rodney L. Parsons、Jeffrey D. Berk、Martin E. Kuehne

  DOI：10.1021/jo00078a029

  日期：1993.12

  The synthesis of N(b)-benzyl-2-(dimethyl 2-malonyl)- and 2-(methyl 2-acetyl)tryptamines (21, 25) provides access to methyl 4-(3-furanyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate (12) and methyl 3-benzyl-5-(3-furanyl)-2,3,3a,4,5,7-hexahydro-1H-pyrrolo[2,3-d]carbazole-6-carboxylate (9), potential intermediates for the syntheses of strychnos alkaloids. A new condensation-sigmatropic rearrangement reaction gives the tetracyclic product 9 directly from the tryptamine 25.