3-(2,4-dimethoxybenzoyl)-1-benzylindole-2-carboxylic acid | 497075-61-3

• 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: 3-(2,4-dimethoxybenzoyl)-1-benzylindole-2-carboxylic acid
• 英文别名: 1-benzyl-3-(2,4-dimethoxybenzoyl)indole-2-carboxylic acid
• CAS: 497075-61-3
• 化学式: C₂₅H₂₁NO₅
• 分子量: 415.445
• InChiKey: FZTDJIMDMWBQAC-UHFFFAOYSA-N

物化性质

• 沸点：
  693.9±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(2,4-dimethoxybenzoyl)-1-benzylindole-2-carboxylic acid 在 chromium(III) oxide 、 copper(II) oxide 作用下， 以 喹啉 为溶剂， 反应 3.0h， 以97%的产率得到1-benzyl-3-(2,4-dimethoxybenzoyl)indole
  参考文献：
  名称：

  Synthesis of 2- and 3-Benzoylindoles by Friedel-Crafts Reaction of Indole-2,3- dicarboxylic Anhydrides with Anisoles

  摘要：

  Reaction of 1-benzylindole-2,3-dicarboxylic anhydride with anisole in the presence of titanium(IV) chloride gave 2-(4-methoxybenzoyl)indole-3-carboxylic acid as the sole product. However, 1-benzenesulfonylindole-2,3-dicarboxylic anhydride with anisole afforded 3-(4-methoxybenzoyl)indole-2-carboxylic acid. These carboxylic acids could be converted to the corresponding benzoylindoles.

  DOI：

  10.3987/com-02-9537
• 作为产物：
  描述：

  1H-呋喃并[3,4-b]吲哚-1,3(4H)-二酮,4-(苯基甲基)- 、 间苯二甲醚 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到3-(2,4-dimethoxybenzoyl)-1-benzylindole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of 2- and 3-Benzoylindoles by Friedel-Crafts Reaction of Indole-2,3- dicarboxylic Anhydrides with Anisoles

  摘要：

  Reaction of 1-benzylindole-2,3-dicarboxylic anhydride with anisole in the presence of titanium(IV) chloride gave 2-(4-methoxybenzoyl)indole-3-carboxylic acid as the sole product. However, 1-benzenesulfonylindole-2,3-dicarboxylic anhydride with anisole afforded 3-(4-methoxybenzoyl)indole-2-carboxylic acid. These carboxylic acids could be converted to the corresponding benzoylindoles.

  DOI：

  10.3987/com-02-9537

文献信息

• Synthesis of Naphth[3,2,1-cd]indole by Heck Cyclization of 2-Methoxycarbonyl- 3-benzoylindoles
  作者：Yasuyoshi Miki、Hideaki Shirokoshi、Mikito Asai、Yoshiyuki Aoki、Hana Matsukida

  DOI：10.3987/com-03-9832

  日期：——

  3-dimethoxybenzene in the presence of titanium(IV) chloride gave the corresponding 3-(2,4-dimethoxybenzoyl)indole-2-carboxylic acid as the sole product. This carboxylic acid could be converted to naphth[3,2,1-cd]indole.

  1-苄基吲哚-2,3-二羧酸酐与1,3-二甲氧基苯在氯化钛(IV)存在下反应得到相应的3-(2,4-二甲氧基苯甲酰基)吲哚-2-羧酸作为唯一产物。这种羧酸可以转化为萘[3,2,1-cd]吲哚。
• Synthesis of 2- and 3-Benzoylindoles by Friedel-Crafts Reaction of Indole-2,3- dicarboxylic Anhydrides with Anisoles
  作者：Yasuyoshi Miki、Yasuhiko Tsuzaki、Chika Kai、Hiroko Hachiken

  DOI：10.3987/com-02-9537

  日期：——

  Reaction of 1-benzylindole-2,3-dicarboxylic anhydride with anisole in the presence of titanium(IV) chloride gave 2-(4-methoxybenzoyl)indole-3-carboxylic acid as the sole product. However, 1-benzenesulfonylindole-2,3-dicarboxylic anhydride with anisole afforded 3-(4-methoxybenzoyl)indole-2-carboxylic acid. These carboxylic acids could be converted to the corresponding benzoylindoles.