ethyl 3,3-diethoxy-2<(1H-indol-2-yl)methyl>aminopropionate | 156571-66-3

• 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: ethyl 3,3-diethoxy-2<(1H-indol-2-yl)methyl>aminopropionate
• 英文别名: ethyl 3,3-diethoxy-2-(1H-indol-2-ylmethylamino)propanoate
• CAS: 156571-66-3
• 化学式: C₁₈H₂₆N₂O₄
• 分子量: 334.415
• InChiKey: UFPXGQWBCJEVOU-UHFFFAOYSA-N

物化性质

• 沸点：
  488.7±45.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3,3-diethoxy-2<(1H-indol-2-yl)methyl>aminopropionate 在 四氯化钛 作用下， 以 苯 为溶剂， 反应 0.17h， 以57%的产率得到β-咔啉-3-羧酸乙酯
  参考文献：
  名称：

  A new efficient synthesis of ethyl β-carboline-3-carboxylate (β-CCE) and methyl 4-methyl-β-carboline-3-carboxylate (4-methyl-β-CCM) starting fr

  摘要：

  Ethyl beta-carboline-3-carboxylate (9) and methyl 4-methyl-beta-carboline-3-carboxylate (15) were prepared in high yields hy condensing indole-2-carboxaldehyde (5) (itself prepared by lithium aluminum hydride reduction of the Weinreb amide derived from indole-2-carboxylic acid) with ethyl 2-amino-3,3-diethoxypropionate (6) and methyl 2-amino-3,3-diethoxybutyrate (12), respectively, followed by reduction of the imine bonds formed with sodium cyanoborohydride and cyclization of the resulting amines (8 and 14, respectively) using titanium (IV) chloride.

  DOI：

  10.1016/s0040-4020(01)80649-9
• 作为产物：
  描述：

  N-甲氧基-N-甲基-1H-吲哚-2-甲酰胺 在 lithium aluminium tetrahydride 、 molecular sieve 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 13.5h， 生成 ethyl 3,3-diethoxy-2<(1H-indol-2-yl)methyl>aminopropionate
  参考文献：
  名称：

  A new efficient synthesis of ethyl β-carboline-3-carboxylate (β-CCE) and methyl 4-methyl-β-carboline-3-carboxylate (4-methyl-β-CCM) starting fr

  摘要：

  Ethyl beta-carboline-3-carboxylate (9) and methyl 4-methyl-beta-carboline-3-carboxylate (15) were prepared in high yields hy condensing indole-2-carboxaldehyde (5) (itself prepared by lithium aluminum hydride reduction of the Weinreb amide derived from indole-2-carboxylic acid) with ethyl 2-amino-3,3-diethoxypropionate (6) and methyl 2-amino-3,3-diethoxybutyrate (12), respectively, followed by reduction of the imine bonds formed with sodium cyanoborohydride and cyclization of the resulting amines (8 and 14, respectively) using titanium (IV) chloride.

  DOI：

  10.1016/s0040-4020(01)80649-9

文献信息

• A new efficient synthesis of ethyl β-carboline-3-carboxylate (β-CCE) and methyl 4-methyl-β-carboline-3-carboxylate (4-methyl-β-CCM) starting fr
  作者：Mouloud Dekhane、Robert H. Dodd

  DOI：10.1016/s0040-4020(01)80649-9

  日期：1994.1

  Ethyl beta-carboline-3-carboxylate (9) and methyl 4-methyl-beta-carboline-3-carboxylate (15) were prepared in high yields hy condensing indole-2-carboxaldehyde (5) (itself prepared by lithium aluminum hydride reduction of the Weinreb amide derived from indole-2-carboxylic acid) with ethyl 2-amino-3,3-diethoxypropionate (6) and methyl 2-amino-3,3-diethoxybutyrate (12), respectively, followed by reduction of the imine bonds formed with sodium cyanoborohydride and cyclization of the resulting amines (8 and 14, respectively) using titanium (IV) chloride.