5,6-dimethoxy-3-(p-tosylamino)indole-2-carbonitrile | 1227096-69-6

• 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: 5,6-dimethoxy-3-(p-tosylamino)indole-2-carbonitrile
• 英文别名: N-(2-cyano-5,6-dimethoxy-1H-indol-3-yl)-4-methylbenzenesulfonamide
• CAS: 1227096-69-6
• 化学式: C₁₈H₁₇N₃O₄S
• 分子量: 371.417
• InChiKey: ARVKQHLONNCZAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-amino-5,6-dimethoxy-1-(p-tosyl)indole-2-carbonitrile 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以79%的产率得到5,6-dimethoxy-3-(p-tosylamino)indole-2-carbonitrile
  参考文献：
  名称：

  Detosylation of 3-amino-1-tosylindole-2-carbonitriles using DBU and thiophenol

  摘要：

  Attempted detosylation of the 3-amino-1-(p-tosylamino)indole-2-carbonitriles 4a-c using either K2CO3 in EtOH or DBU in PhH at reflux gives unexpectedly the 3-(N-p-tosylamino)indole-2-carbonitriles 5a-c, respectively in high yields. Nevertheless, treatment of 1-(p-tosylamino)indoles 4a-c with thiophenol and DBU in PhH at reflux gives the detosylated 3-aminoindole-2-carbonitriles 5a-c. Reaction mechanisms supporting the tosyl migration (4 -> 5) and the reductive detosylation (4 -> 2) are proposed. All new compounds are fully characterised. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.02.058

文献信息

• Detosylation of 3-amino-1-tosylindole-2-carbonitriles using DBU and thiophenol
  作者：Sophia S. Michaelidou、Panayiotis A. Koutentis

  DOI：10.1016/j.tet.2010.02.058

  日期：2010.4

  Attempted detosylation of the 3-amino-1-(p-tosylamino)indole-2-carbonitriles 4a-c using either K2CO3 in EtOH or DBU in PhH at reflux gives unexpectedly the 3-(N-p-tosylamino)indole-2-carbonitriles 5a-c, respectively in high yields. Nevertheless, treatment of 1-(p-tosylamino)indoles 4a-c with thiophenol and DBU in PhH at reflux gives the detosylated 3-aminoindole-2-carbonitriles 5a-c. Reaction mechanisms supporting the tosyl migration (4 -> 5) and the reductive detosylation (4 -> 2) are proposed. All new compounds are fully characterised. (C) 2010 Elsevier Ltd. All rights reserved.