1-benzenesulfonylindole-2,3-dicarboxylic anhydride | 192991-42-7

• 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: 1-benzenesulfonylindole-2,3-dicarboxylic anhydride
• 英文别名: 4-(Benzenesulfonyl)furo[3,4-b]indole-1,3-dione
• CAS: 192991-42-7
• 化学式: C₁₆H₉NO₅S
• 分子量: 327.317
• InChiKey: BECDVDSTGCCCBN-UHFFFAOYSA-N

物化性质

• 沸点：
  593.4±42.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-benzenesulfonylindole-2,3-dicarboxylic anhydride 在 硫酸 、 碳酸氢钠 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 16.5h， 生成 (E)-1-(3-methoxycarbonylindol-2-yl)-2-propen-1-one
  参考文献：
  名称：

  Reaction of 1-Benzenesulfonylindole-2,3-dicarboxylic Anhydride with Wittig Reagents: Synthesis of Pyrrolo[1,2-a]indoles and Cyclopent[b]indole

  摘要：

  Treatment of 1-benzenesulfonylindole-2,3-dicarboxylic anhydride with methylenetriphenylphosphorane gave the corresponding ylide. After esterification of the carboxyl group and removal of the benzenesulfonyl group of the ylide, the obtained ylide was reacted with aldehydes to yield alpha,beta -unsaturated ketones, which were converted to pyrrolo[1,2-a]indoles. We also examined the reactivity of the anhydride with (carbethoxymethylene)triphenylphosphorane and (carbethoxyethylidene)triphenylphosphorane.

  DOI：

  10.3987/com-01-9230
• 作为产物：
  描述：

  1-(phenylsulfonyl)indole-2,3-dicarboxylic acid 在 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以77%的产率得到1-benzenesulfonylindole-2,3-dicarboxylic anhydride
  参考文献：
  名称：

  Reaction of Indole-2,3-dicarboxylic Anhydride with Grignard Reagents: Synthesis of 2-Acylindoles

  摘要：

  Reaction of indole-2,3-dicarboxylic anhydride with methylmagnesium bromide and phenylmagnesium bromide gave 2-acetyl- and 2-benzoyl-indole-3-carboxylic acids, but with tert-butylmagnesium chloride, 3-pivaloylindole-2-carboxylic acids were obtained as the main products. Treatment of 2-acylindole-3-carboxylic acids with copper chromite in quinoline or potassium hydroxide gave the corresponding 2-acylindoles.

  DOI：

  10.3987/com-97-7806

文献信息

• Synthesis of caulersin and its isomers by reaction of indole-2,3-dicarboxylic anhydrides with methyl indoleacetates
  作者：Yasuyoshi Miki、Yosiyuki Aoki、Hideaki Miyatake、Toshie Minematsu、Hajime Hibino

  DOI：10.1016/j.tetlet.2006.04.157

  日期：2006.7

  1-Benzenesulfonylindole-2,3-dicarboxylic anhydride was reacted with methyl 1-benzenesulfonylindole-2-acetate to give the corresponding 2-acylindole-3-carboxylic acid as the sole product in high yield, which could be converted to caulersin in four steps. In a similar manner, three isomers A, B, and C were synthesized by reaction of indole-2,3-dicarboxylic anhydrides with methyl indoleacetates.

  使1-苯磺酰基吲哚-2，3-二羧酸酐与1-苯磺酰基吲哚-2-乙酸甲酯反应，以高收率得到相应的2-酰基吲哚-3-羧酸为唯一产物，该产物可通过四步转化为花椰菜素。以类似的方式，通过吲哚-2，3-二羧酸酐与吲哚乙酸甲酯的反应合成了三种异构体A，B和C。
• Synthesis of benzo-γ-carboline alkaloid cryptosanginolentine by reaction of indole-2,3-dicarboxylic anhydrides with anilines
  作者：Yasuyoshi Miki、Makoto Kuromatsu、Hideaki Miyatake、Hiromi Hamamoto

  DOI：10.1016/j.tetlet.2007.10.130

  日期：2007.12

  1-Benzenesulfonylindole-2,3-dicarboxylic anhydride was reacted with aniline to give the 2-carbamoylindole-3-carboxylic acid as the sole product, but with N-methylaniline, the 3-carbamoylindole-2-carboxylic acid was the major product, which could be transformed into the 1-benzenesulfonylbenzo-γ-carbolinone in the presence of Pd(OCOCF3)2. The reduction of the benzo-γ-carbolinone with LiAlH4 gave the

  使1-苯磺酰亚吲哚-2,3-二羧酸酐与苯胺反应，以生成2-氨基甲酰基吲哚-3-羧酸为唯一产物，但与N-甲基苯胺一起，以3-氨基甲酰基吲哚-2-羧酸为主要产物，在Pd（OCOCF 3）2存在下，可将其转化为1-苯磺酰基苯并-γ-咔啉酮。用LiAlH 4还原苯并-γ-咔啉酮可得到高产率的隐山茱lent素。
• 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.
• Reaction of 1-Benzenesulfonylindole-2,3-dicarboxylic Anhydride with Wittig Reagents: Synthesis of Pyrrolo[1,2-a]indoles and Cyclopent[b]indole
  作者：Yasuyoshi Miki、Hiroko Hachiken、Atsuko Kawazoe、Yasuhiko Tsuzaki、Norihide Yanase

  DOI：10.3987/com-01-9230

  日期：——

  Treatment of 1-benzenesulfonylindole-2,3-dicarboxylic anhydride with methylenetriphenylphosphorane gave the corresponding ylide. After esterification of the carboxyl group and removal of the benzenesulfonyl group of the ylide, the obtained ylide was reacted with aldehydes to yield alpha,beta -unsaturated ketones, which were converted to pyrrolo[1,2-a]indoles. We also examined the reactivity of the anhydride with (carbethoxymethylene)triphenylphosphorane and (carbethoxyethylidene)triphenylphosphorane.
• Reaction of Indole-2,3-dicarboxylic Anhydride with Grignard Reagents: Synthesis of 2-Acylindoles
  作者：Yasuyoshi Miki、Hiroko Hachiken、Ichigo Yoshikawa

  DOI：10.3987/com-97-7806

  日期：——

  Reaction of indole-2,3-dicarboxylic anhydride with methylmagnesium bromide and phenylmagnesium bromide gave 2-acetyl- and 2-benzoyl-indole-3-carboxylic acids, but with tert-butylmagnesium chloride, 3-pivaloylindole-2-carboxylic acids were obtained as the main products. Treatment of 2-acylindole-3-carboxylic acids with copper chromite in quinoline or potassium hydroxide gave the corresponding 2-acylindoles.