N-methanesulfonyl-2-(2-bromocyclohex-1-en-1-yl)aniline | 686348-39-0

• 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: N-methanesulfonyl-2-(2-bromocyclohex-1-en-1-yl)aniline
• 英文别名: N-[2-(2-bromocyclohexen-1-yl)phenyl]methanesulfonamide
• CAS: 686348-39-0
• 化学式: C₁₃H₁₆BrNO₂S
• 分子量: 330.246
• InChiKey: UQSKIVJBNYQVTO-UHFFFAOYSA-N

物化性质

• 沸点：
  439.7±55.0 °C(Predicted)
• 密度：
  1.537±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2',3',4',5'-tetrahydro-[1,1'-biphenyl]-2-amine 在 N-溴代丁二酰亚胺(NBS) 、 碳酸氢钠 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 N-methanesulfonyl-2-(2-bromocyclohex-1-en-1-yl)aniline
  参考文献：
  名称：

  New synthesis of 9-methanesulfonyl-1,2,3,9a-tetrahydro- and 1,2,3,4-tetrahydrocarbazoles from N-methanesulfonyl-2-(cyclohex-1-enyl)aniline

  摘要：

  The reaction of N-methanesulfonyl-2-(cyclohex-1-en-1-yl)aniline with Br-2 in the presence of NaHCO3 in MeCN results in N-methanesulfonyl-2-(6-bromocyclohex-1-en-1-yl)aniline, which was cyclised to 9-methanesulfonyl-1,2,3,4-tetrahydrocarbazole, and the effect of NH3 leads to 9-methanesulfonyl-1,2,3,9a-tetrahydrocarbazole. The reaction of the latter with molecular bromine in the presence of pyridine results in 1-(9-methanesulfonyl-1,2,3,4-tetrahydro-4-carbazolyl)pyridinium bromide in a good yield.

  DOI：

  10.1070/mc2003v013n05abeh001699

文献信息

• New synthesis of 9-methanesulfonyl-1,2,3,9a-tetrahydro- and 1,2,3,4-tetrahydrocarbazoles from N-methanesulfonyl-2-(cyclohex-1-enyl)aniline
  作者：Rail R. Gataullin、Alexander M. Sotnikov、Ildus B. Abdrakhmanov、Genrikh A. Tolstikov

  DOI：10.1070/mc2003v013n05abeh001699

  日期：2003.1

  The reaction of N-methanesulfonyl-2-(cyclohex-1-en-1-yl)aniline with Br-2 in the presence of NaHCO3 in MeCN results in N-methanesulfonyl-2-(6-bromocyclohex-1-en-1-yl)aniline, which was cyclised to 9-methanesulfonyl-1,2,3,4-tetrahydrocarbazole, and the effect of NH3 leads to 9-methanesulfonyl-1,2,3,9a-tetrahydrocarbazole. The reaction of the latter with molecular bromine in the presence of pyridine results in 1-(9-methanesulfonyl-1,2,3,4-tetrahydro-4-carbazolyl)pyridinium bromide in a good yield.