methyl 2-(1-carbomethoxy-3-indolyl)-2-ethoxyacetate | 1227640-52-9

• 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: methyl 2-(1-carbomethoxy-3-indolyl)-2-ethoxyacetate
• 英文别名: Methyl 3-(1-ethoxy-2-methoxy-2-oxoethyl)indole-1-carboxylate；methyl 3-(1-ethoxy-2-methoxy-2-oxoethyl)indole-1-carboxylate
• CAS: 1227640-52-9
• 化学式: C₁₅H₁₇NO₅
• 分子量: 291.304
• InChiKey: YGJNOUZUQCCXOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-methoxycarbonyl-3-indoleacetic acid methyl ester 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 8.0h， 生成 methyl 2-(1-carbomethoxy-3-indolyl)-2-ethoxyacetate 、 ethyl 2-(1-carbomethoxy-3-indolyl)-2-ethoxyacetate
  参考文献：
  名称：

  Regioselective Synthesis of 3-Indolyl(alkoxy)acetates

  摘要：

  The regioselective synthesis of N-carbomethoxy-2-alkoxyindolenines and alpha-alkoxyindoles is reported. Bromination of indole 5 with NBS/AIBN/CCl(4) gave alpha-bromoindole 6 which after treatment with ROH/3 angstrom molecular Sieves afforded (Z-) and (E)-2-alkoxyindolenines 8a-d as the main products, together with minor amounts of alpha-alkoxyindoles 9a-d. The reversed regioselectivity was achieved in the absence of molecular Sieves to give alpha-alkoxyindoles 9a-d as the main products, while no traces of Z- or E-8a-d were detected.

  DOI：

  10.3987/com-10-11904

文献信息

• Regioselective Synthesis of 3-Indolyl(alkoxy)acetates
  作者：Oscar R. Suárez-Castillo、Myriam Meléndez-Rodríguez、Indira C. Cano-Escudero、Sandra Luz De Ita-Gutiérrez、Maricruz Sánchez-Zavala、Martha S. Morales-Ríos、Pedro Joseph-Nathan

  DOI：10.3987/com-10-11904

  日期：——

  The regioselective synthesis of N-carbomethoxy-2-alkoxyindolenines and alpha-alkoxyindoles is reported. Bromination of indole 5 with NBS/AIBN/CCl(4) gave alpha-bromoindole 6 which after treatment with ROH/3 angstrom molecular Sieves afforded (Z-) and (E)-2-alkoxyindolenines 8a-d as the main products, together with minor amounts of alpha-alkoxyindoles 9a-d. The reversed regioselectivity was achieved in the absence of molecular Sieves to give alpha-alkoxyindoles 9a-d as the main products, while no traces of Z- or E-8a-d were detected.