1-(phenylsulfonyl)-3-bromoindole-2-carboxylic acid | 1203550-92-8

• 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-(phenylsulfonyl)-3-bromoindole-2-carboxylic acid
• 英文别名: 1-benzenesulfonyl-3-bromoindole-2,carboxylic acid；3-Bromo-1-(phenylsulfonyl)-1H-indole-2-carboxylic acid；1-(benzenesulfonyl)-3-bromoindole-2-carboxylic acid
• CAS: 1203550-92-8
• 化学式: C₁₅H₁₀BrNO₄S
• 分子量: 380.219
• InChiKey: OGXLVLKKRJZFMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(phenylsulfonyl)-3-bromoindole-2-carboxylic acid 在 碘苯二乙酸 、 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以80%的产率得到2,3-Dibromo-1-(phenylsulfonyl)indole
  参考文献：
  名称：

  Decarboxylative Halogenation of Indolecarboxylic Acids Using Hypervalent Iodine(III) Reagent and Its Application to the Synthesis of Polybromoindoles

  摘要：

  Hypervalent iodine mediated decarboxylative halogenation of indoledicarboxylic acid derivatives was studied. The treatment of 1-methylindole-2,3-dicarboxylic acid with phenyliodine diacetate (PIDA) in the presence of lithium bromide gave 1-methyl-3,3-bromooxindole. However, the reaction of 1-(phenylsulfonyl)indole-2,3-dicarboxylic acid with PIDA in the presence of lithium bromide afforded 2,3-dibromo-1-(phenylsulfonyl)indole. In a similar manner, the 2,3-dichloro- and 2,3-diiodoindole derivatives could be obtained by the reaction of the indole-2,3-dicarboxylic acids with PIDA in the presence of lithium chloride and iodide. This method was optimized to the synthesis of polybromoindole alkaloids.

  DOI：

  10.3987/com-14-13162
• 作为产物：
  描述：

  1-(苯磺酰基)-1H-吲哚-2-羧酸 在 碘苯二乙酸 、 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以80%的产率得到1-(phenylsulfonyl)-3-bromoindole-2-carboxylic acid
  参考文献：
  名称：

  Decarboxylative Halogenation of Indolecarboxylic Acids Using Hypervalent Iodine(III) Reagent and Its Application to the Synthesis of Polybromoindoles

  摘要：

  Hypervalent iodine mediated decarboxylative halogenation of indoledicarboxylic acid derivatives was studied. The treatment of 1-methylindole-2,3-dicarboxylic acid with phenyliodine diacetate (PIDA) in the presence of lithium bromide gave 1-methyl-3,3-bromooxindole. However, the reaction of 1-(phenylsulfonyl)indole-2,3-dicarboxylic acid with PIDA in the presence of lithium bromide afforded 2,3-dibromo-1-(phenylsulfonyl)indole. In a similar manner, the 2,3-dichloro- and 2,3-diiodoindole derivatives could be obtained by the reaction of the indole-2,3-dicarboxylic acids with PIDA in the presence of lithium chloride and iodide. This method was optimized to the synthesis of polybromoindole alkaloids.

  DOI：

  10.3987/com-14-13162

文献信息

• Hypervalent Iodine(III) Mediated Decarboxylative Halogenation of Indolecarboxylic Acids for the Synthesis of Haloindole Derivatives
  作者：Yasuyoshi Miki、Hiromi Hamamoto、Hideaki Umemoto、Misako Umemoto、Chiaki Ohta、Masashi Dohshita

  DOI：10.1055/s-0030-1258585

  日期：2010.10

  The treatment of 1-methylindole-2,3-dicarboxylic acid with hypervalent iodine(III) reagent, phenyliodine diacetate (PI-DA), in the presence of lithium bromide gave 1-methyl-3,3-dibromooxindole. However, the reaction of 1-(phenylsulfonyl)indole-2,3-dicarboxylic acid with PIDA in the presence of lithium bromide afforded 2,3-dibromo-1-(phenylsulfonyl)indole. In a similar manner, the 2,3-dichloro- and

  在溴化锂存在下，用高价碘 (III) 试剂、二乙酸苯碘 (PI-DA) 处理 1-甲基吲哚-2,3-二羧酸得到 1-甲基-3,3-二溴吲哚。然而，在溴化锂存在下，1-(苯基磺酰基)吲哚-2,3-二羧酸与PIDA反应得到2,3-二溴-1-(苯基磺酰基)吲哚。以类似的方式，2,3-二氯-和2,3-二碘-吲哚衍生物是通过吲哚-2,3-二羧酸与PIDA在氯化锂和碘化锂存在下的反应获得的。
• [EN] SUBSTITUTED INDOLES WITH SEROTONIN RECEPTOR AFFINITY, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] INDOLES SUBSTITUES DOTES D'UNE AFFINITE POUR LE RECEPTEUR DE LA SEROTONINE, LEUR PROCEDE DE FABRICATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：SUVEN LIFE SCIENCES LTD

  公开号：WO2004108671A1

  公开（公告）日：2004-12-16

  The present invention relates to the compounds represented by general formula (I) as shown below.

  本发明涉及如下所示的一般式(I)所代表的化合物。
• Decarboxylative Bromination of Indole-2,3-dicarboxylic Acids Using Oxone® or CAN in the Presence of Lithium Bromide
  作者：Yasuyoshi Miki、Hideaki Umemoto、Misako Umemoto、Chiaki Ohta、Masashi Dohshita、Hiroki Tanaka、Syo Hattori、Hiromi Hamamoto

  DOI：10.3987/com-09-11802

  日期：——

  The treatment of 1-methylindole-2,3-dicarboxylic acid with Oxone (R) and lithium bromide produced 3,3-dibromo-1-methyloxindole. However, the reaction of 1-benzenesulfonylindole-2,3-dicarboxylic acid with Oxone (R) and lithium bromide afforded 1-benzenesulfonyl-2,3-dibromoindole. In a similar manner, 2,3,5,6-tetrabromoindole was synthesized from 1-benzenesulfonyl-5,6-dibromoindole-2,3-dicarboxylic acid.
• Decarboxylative Halogenation of Indolecarboxylic Acids Using Hypervalent Iodine(III) Reagent and Its Application to the Synthesis of Polybromoindoles
  作者：Hiromi Hamamoto、Yasuyoshi Miki、Hideaki Umemoto、Misako Umemoto、Chiaki Ohta、Emi Fujita、Akira Nakamura、Tomohiro Maegawa

  DOI：10.3987/com-14-13162

  日期：——

  Hypervalent iodine mediated decarboxylative halogenation of indoledicarboxylic acid derivatives was studied. The treatment of 1-methylindole-2,3-dicarboxylic acid with phenyliodine diacetate (PIDA) in the presence of lithium bromide gave 1-methyl-3,3-bromooxindole. However, the reaction of 1-(phenylsulfonyl)indole-2,3-dicarboxylic acid with PIDA in the presence of lithium bromide afforded 2,3-dibromo-1-(phenylsulfonyl)indole. In a similar manner, the 2,3-dichloro- and 2,3-diiodoindole derivatives could be obtained by the reaction of the indole-2,3-dicarboxylic acids with PIDA in the presence of lithium chloride and iodide. This method was optimized to the synthesis of polybromoindole alkaloids.