1-benzenesulfonyl-2-(4-methoxybenzoyl)indole-3-carboxylic acid | 496869-52-4

• 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: 1-benzenesulfonyl-2-(4-methoxybenzoyl)indole-3-carboxylic acid
• 英文别名: 1-(benzenesulfonyl)-2-(4-methoxybenzoyl)indole-3-carboxylic acid
• CAS: 496869-52-4
• 化学式: C₂₃H₁₇NO₆S
• 分子量: 435.457
• InChiKey: IPSDLNODXPVIPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  102.67
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-benzenesulfonyl-2-(4-methoxybenzoyl)indole-3-carboxylic acid 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以84%的产率得到(1H-吲哚-2-基)(4-甲氧基苯基)甲酮
  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：

  苯甲醚 、 1-benzenesulfonylindole-2,3-dicarboxylic anhydride 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到1-benzenesulfonyl-2-(4-methoxybenzoyl)indole-3-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 5H-Benzo[b]carbazole- 6,11-diones from Benzoylindolecarboxylic Acids
  作者：Yasuyoshi Miki、Yasuhiko Tsuzaki、Hana Matsukida

  DOI：10.3987/com-02-9538

  日期：——

  Treatment of 1-benzyl-3-(4-methoxybenzoyl)indole-2-carboxylic acid with phosphorus pentachloride gave the corresponding acid chloride, which was treated with titanium(IV) chloride to afford 9-methoxy-5H-benzo[b]carbazole-6, 11-dione. In a similar manner, 1-benzenesulfonyl-2-(4-methoxybenzoyl)indole-3-carboxylic acid provided 9-methoxy-5H-benzo[b]carbazole-6,11-dione. However, 1-benzyl-3-(4-methoxybenzyl)indole-2-carboxylic acid could be converted to 8-methoxy-5H-benzo[b]carbazole-6,11-dione.