5-Bromo-1-(4-methylphenyl)sulfonylindole-2-carbaldehyde | 1191382-31-6

• 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: 5-Bromo-1-(4-methylphenyl)sulfonylindole-2-carbaldehyde
• 英文别名: 5-bromo-1-(4-methylphenyl)sulfonylindole-2-carbaldehyde
• CAS: 1191382-31-6
• 化学式: C₁₆H₁₂BrNO₃S
• 分子量: 378.246
• InChiKey: BIMSCRZWLKSUQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  64.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-tosyl-5-bromoindole 、 N,N-二甲基甲酰胺 在 双二甲胺基乙基醚 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 、 甲苯 为溶剂， 以97%的产率得到5-Bromo-1-(4-methylphenyl)sulfonylindole-2-carbaldehyde
  参考文献：
  名称：

  Stabilizing N-tosyl-2-lithioindoles with bis(N,N′-dimethylaminoethyl) ether—a non-cryogenic procedure for lithiation of N-tosylindoles and subsequent addition to ketones

  摘要：

  A practical procedure suitable for large scale lithiation of N-tosylindoles and subsequent addition to ketones is described. Bis(N,N'-dimethylaminoethyl) ether was found to stabilize 2-lithio-N-tosylindole 1A at -25 degrees C [The temperatures cited are internal temperatures unless otherwise stated]. Addition of this reagent allows the lithiation of N-tosyl indoles and subsequent addition to ketones to operate at -25 degrees C, a temperature suitable for large scale reactions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.120

文献信息

• Stabilizing N-tosyl-2-lithioindoles with bis(N,N′-dimethylaminoethyl) ether—a non-cryogenic procedure for lithiation of N-tosylindoles and subsequent addition to ketones
  作者：Jiang-Ping Wu、Sanjit Sanyal、Zhi-Hui Lu、Chris H. Senanayake

  DOI：10.1016/j.tetlet.2009.07.120

  日期：2009.10

  A practical procedure suitable for large scale lithiation of N-tosylindoles and subsequent addition to ketones is described. Bis(N,N'-dimethylaminoethyl) ether was found to stabilize 2-lithio-N-tosylindole 1A at -25 degrees C [The temperatures cited are internal temperatures unless otherwise stated]. Addition of this reagent allows the lithiation of N-tosyl indoles and subsequent addition to ketones to operate at -25 degrees C, a temperature suitable for large scale reactions. (C) 2009 Elsevier Ltd. All rights reserved.