Ethyl 1-(2,6-dimethoxyphenyl)-3-(4'-anilino-3',5'-dimethoxyphenyl)indole-2-carboxylate | 131157-34-1

• 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: Ethyl 1-(2,6-dimethoxyphenyl)-3-(4'-anilino-3',5'-dimethoxyphenyl)indole-2-carboxylate
• 英文别名: ethyl 3-(4-anilino-3,5-dimethoxyphenyl)-1-(2,6-dimethoxyphenyl)indole-2-carboxylate
• CAS: 131157-34-1
• 化学式: C₃₃H₃₂N₂O₆
• 分子量: 552.627
• InChiKey: VBYNMNGUQVJZMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.25
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  80.18
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  ethyl (2E)-2-[(2,6-dimethoxyphenyl)-phenylhydrazinylidene]propanoate 、 氯化锌 、 溶剂黄146 生成 Ethyl 1-(2,6-dimethoxyphenyl)-3-(4'-anilino-3',5'-dimethoxyphenyl)indole-2-carboxylate
  参考文献：
  名称：

  ISHII, HISASHI;SUGIURA, TAKAO;AKIYAMA, YOHKO;ICHIKAWA, YOSHIE;WATANABE, T+, CHEM. AND PHARM. BULL., 38,(1990) N, C. 2118-2126

  摘要：

  DOI：

文献信息

• Fischer indolization and its related compounds. XXIII. Fischer indolization of ethyl pyruvate 2-(2,6-dimethoxyphenyl)phenylhydrazone.
  作者：Hisashi ISHII、Takao SUGIURA(nee HAGIWARA)、Yohko AKIYAMA(nee KONDO)、Yoshie ICHIKAWA、Toshiko WATANABE、Yasuoki MURAKAMI

  DOI：10.1248/cpb.38.2118

  日期：——

  In order to clarify the mechanism of the abnormal Fischer indolization of 2-methoxyphenylhydrazones the Fischer indolization of ethly pyruvate 2-(2, 6-dimethoxyphenyl)phenylhydrazone (6) was undertaken using ethanolic hydrogen chloride and zinc chloride as an acid catalyst. The cyclization was found to take place predominantly on the 2, 6-dimethoxyphenyl nucleus to give the corresponding indoles, although the yields of indoles formed were low. Some non-indolic by-products were also produced which might give information about the mechanism of Fischer indolization. In particular, the formation of 3, 5-dimethoxy-4-anilinobenzaldehyde (15) suggests that the first cyclization step in Fischer indolization could take place at the para position of phenylhydrazone as a side reaction.

  为了澄清2-甲氧基苯腈的异常费希尔吲哚化反应的机制，研究了乙基丙酮2-(2, 6-二甲氧基苯基)苯腈（6）的费希尔吲哚化反应，使用了氯化氢乙醇溶液和氯化锌作为酸催化剂。结果发现，环化主要发生在2, 6-二甲氧基苯核上，生成相应的吲哚，尽管所形成的吲哚产率较低。此外，还产生了一些非吲哚的副产品，这可能提供有关费希尔吲哚化机制的信息。特别是，3, 5-二甲氧基-4-苯胺醛（15）的形成提示，费希尔吲哚化反应的第一个环化步骤可能作为副反应发生在苯腈的对位。