ethyl 5-(indol-3'-yl)-3,3-dimethylpentanoate | 141972-38-5

• 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: ethyl 5-(indol-3'-yl)-3,3-dimethylpentanoate
• 英文别名: ethyl 5-(1H-indol-3-yl)-3,3-dimethylpentanoate
• CAS: 141972-38-5
• 化学式: C₁₇H₂₃NO₂
• 分子量: 273.375
• InChiKey: YFYMCOFAFZMMFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  42.09
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ethyl 5-(indol-3'-yl)-3,3-dimethylpentanoate 在 四氯化碳 、 4-二甲氨基吡啶 、 lithium cyclohexylisopropylamide 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 17.83h， 生成 ethyl 3,4,5,6-tetrahydro-5,5-dimethyl-1H-cycloheptindole-6-carboxylate
  参考文献：
  名称：

  Synthesis of 3,4-bridged indoles by photocyclisation reactions. Part 2. Photocyclisation of halogenoacetyl tryptophol derivatives and α-chloro indol-3-ylalkanoate esters

  摘要：

  Irradiation of the trichloroacetates 2, 4 and 5, derived from the corresponding tryptophols, in methanolic acetonitrile results in photocyclisation to the indole 4-position, and the formation of the pyrrolobenzoxocines 9-11. Attempted photocyclisation of the 'reversed' alpha-chloro esters 15a, 15b and 18 was thwarted by readily occurring elimination of HCl, although the dimethyl compound 15c did cyclise to give the cycloheptaindole 20 upon irradiation in acetonitrile.

  DOI：

  10.1039/p19920000813
• 作为产物：
  描述：

  吲哚 、 4,4-dimethyl-tetrahydro-pyran-2-one 生成 ethyl 5-(indol-3'-yl)-3,3-dimethylpentanoate
  参考文献：
  名称：

  Synthesis of 3,4-bridged indoles by photocyclisation reactions. Part 2. Photocyclisation of halogenoacetyl tryptophol derivatives and α-chloro indol-3-ylalkanoate esters

  摘要：

  Irradiation of the trichloroacetates 2, 4 and 5, derived from the corresponding tryptophols, in methanolic acetonitrile results in photocyclisation to the indole 4-position, and the formation of the pyrrolobenzoxocines 9-11. Attempted photocyclisation of the 'reversed' alpha-chloro esters 15a, 15b and 18 was thwarted by readily occurring elimination of HCl, although the dimethyl compound 15c did cyclise to give the cycloheptaindole 20 upon irradiation in acetonitrile.

  DOI：

  10.1039/p19920000813