1-(phenylsulfonyl)-2,3,5,6-tetrabromoindole | 1203551-05-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(phenylsulfonyl)-2,3,5,6-tetrabromoindole
• 英文别名: 1-benzenesulfonyl-2,3,5,6-tetrabromoindole
• CAS: 1203551-05-6
• 化学式: C₁₄H₇Br₄NO₂S
• 分子量: 572.897
• InChiKey: PXYCDSIFLUUOMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.93
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.07
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(phenylsulfonyl)-2,3,5,6-tetrabromoindole 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到2,3,5,6-四溴-1H-吲哚
  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：

  5,6-dibromo-1-(phenylsulfonyl)indole-2,3-dicarboxylic acid 在 碘苯二乙酸 、 potassium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以83%的产率得到1-(phenylsulfonyl)-2,3,5,6-tetrabromoindole
  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

• 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.