methyl 3-(1-bromo-2-methoxy-2-oxoethyl)-1H-indole-1-carboxylate | 1227640-42-7

• 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 3-(1-bromo-2-methoxy-2-oxoethyl)-1H-indole-1-carboxylate
• CAS: 1227640-42-7
• 化学式: C₁₃H₁₂BrNO₄
• 分子量: 326.147
• InChiKey: WINBXWZMSWWTDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  57.53
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 methyl 3-(1-bromo-2-methoxy-2-oxoethyl)-1H-indole-1-carboxylate 反应 4.0h， 以85%的产率得到methyl 2-(1-carbomethoxy-3-indolyl)-2-methoxyacetate
  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
• 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 2.0h， 以87%的产率得到methyl 3-(1-bromo-2-methoxy-2-oxoethyl)-1H-indole-1-carboxylate
  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