2-dimethylaminoethyl indole-3-acetate | 107518-08-1

• 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: 2-dimethylaminoethyl indole-3-acetate
• 英文别名: Indolessigsaeure-(3)-(2-dimethylamino-ethylester)；2-(dimethylamino)ethyl 2-(1H-indol-3-yl)acetate
• CAS: 107518-08-1
• 化学式: C₁₄H₁₈N₂O₂
• 分子量: 246.309
• InChiKey: PYVZKKKVLJWGJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-dimethylaminoethyl indole-3-acetate 、 碘甲烷 以 乙酸乙酯 为溶剂， 反应 1.5h， 以60%的产率得到indole-3-acetylcholine
  参考文献：
  名称：

  A versatile and efficient methodology for the preparation of choline ester auxin conjugates

  摘要：

  A two-step synthetic strategy affords indole-3-acetylcholine (IAC) from indole-3-acetic acid (IAA) via the intermediacy of 2-dimethylaminoethyl indole-3-acetate. Thus, treatment of indole-3-acetate with 1-dimethylamino-2 chloroethane, followed by methylation with methyl iodide, yields 55-70% recrystallized IAC from IAA. Using the same methodology, six analogues of IAC have been prepared in overall yields ranging from 40 to 60%.

  DOI：

  10.1016/0031-9422(95)00460-o
• 作为产物：
  描述：

  3-吲哚乙酸 、 2-氯-N,N-二甲基乙胺 在 potassium carbonate 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 以53%的产率得到2-dimethylaminoethyl indole-3-acetate
  参考文献：
  名称：

  A versatile and efficient methodology for the preparation of choline ester auxin conjugates

  摘要：

  A two-step synthetic strategy affords indole-3-acetylcholine (IAC) from indole-3-acetic acid (IAA) via the intermediacy of 2-dimethylaminoethyl indole-3-acetate. Thus, treatment of indole-3-acetate with 1-dimethylamino-2 chloroethane, followed by methylation with methyl iodide, yields 55-70% recrystallized IAC from IAA. Using the same methodology, six analogues of IAC have been prepared in overall yields ranging from 40 to 60%.

  DOI：

  10.1016/0031-9422(95)00460-o

文献信息

• A versatile and efficient methodology for the preparation of choline ester auxin conjugates
  作者：Balázs A. Bozsó、Richard A. Fluck、Rachel A. Jameton、Phyllis A. Leber、Jeffrey G. Varnes

  DOI：10.1016/0031-9422(95)00460-o

  日期：1995.11

  A two-step synthetic strategy affords indole-3-acetylcholine (IAC) from indole-3-acetic acid (IAA) via the intermediacy of 2-dimethylaminoethyl indole-3-acetate. Thus, treatment of indole-3-acetate with 1-dimethylamino-2 chloroethane, followed by methylation with methyl iodide, yields 55-70% recrystallized IAC from IAA. Using the same methodology, six analogues of IAC have been prepared in overall yields ranging from 40 to 60%.