N-methylsulfonyl-2-(cyclopent-1-en-1-yl)-6-methylaniline | 538367-63-4

• 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-methylsulfonyl-2-(cyclopent-1-en-1-yl)-6-methylaniline
• 英文别名: N-mesyl-6-methyl-2-(1-cyclopenten-1-yl)aniline；N-[2-(cyclopenten-1-yl)-6-methylphenyl]methanesulfonamide
• CAS: 538367-63-4
• 化学式: C₁₃H₁₇NO₂S
• 分子量: 251.349
• InChiKey: TWUSBTFTKQXBGR-UHFFFAOYSA-N

物化性质

• 沸点：
  382.4±52.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 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

• 作为反应物：
  描述：

  N-methylsulfonyl-2-(cyclopent-1-en-1-yl)-6-methylaniline 在 氢氧化钾 、 双氧水 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 5.0h， 以62%的产率得到N-methanesulfonyl-2-methyl-6-(2-oxocyclopent-1-yl)aniline
  参考文献：
  名称：

  Synthesis of derivatives of o-aminoacetophenone and o-aminobenzyl alcohol

  摘要：

  Oxidation of 2'-hydroxy-8-methylspiro[4H-benz-1,3-oxazin-2-one-6,1'-cyclopentane] or N-mesyl-2-(cyclopent-1-en-1-yl)-6-methylaniline provided the corresponding ketones. The rearrangement of these ketones oximes under treatment with thionyl chloride gave rise to nitriles of 5-(2-amino-3-methylphenyl)-5-oxopentanoic or 5-(2-methanesulfamido-3-methylphenyl)-5-hydroxypentanoic acids. By heating 5-(2-acetylamido-3-methylphenyl)-5-oxopentanoic acid with LiH in THF3-(2,8-dimethylquinol-4-on-3-yl)propanoic acid was obtained.

  DOI：

  10.1134/s1070428007050132
• 作为产物：
  描述：

  2-(cyclopent-1-enyl)-6-methylaniline 、 甲基磺酰氯 生成 N-methylsulfonyl-2-(cyclopent-1-en-1-yl)-6-methylaniline
  参考文献：
  名称：

  摘要：

  The formation and fragmentation of negative ions of some N-(methylsulfonyl)anilines upon resonance electron capture have been studied. The formation of long-living molecular ions is due to the presence of the mesyl groups in the molecules. The difference in negative-ion mass spectra of isomeric N-(methylsulfonyl)anilines has been revealed.

  DOI：

  10.1023/a:1022108023832

文献信息

• Reaction of N-methylsulfonyl-and N-(p-tolylsulfonyl)-2-(cyclopent-1-en-1-yl)anilines with bromine in the presence of potassium thiocyanate and in methanol
  作者：R. R. Gataullin、A. A. Fatykhov

  DOI：10.1134/s1070363208030183

  日期：2008.3

  The reactions of N-methylsulfonyl- and N-(p-tolylsulfonyl)-2-(cyclopent-1-en-1-yl)-6-methylaniline with molecular bromine in the presence of potassium thiocyanate gave N-methylsulfonyl- and N-(p-tolylsulfonyl)-2-(5-isothiocyanatocyclopent-1-en-1-yl)-6-methylanilines. N-Methylsulfonyl-2-(cyclopent-1-en-1-yl)-6-methylanihne reacted with bromine in methanol in the presence of NaHCO3 or with CuBr2 in MeOH to afford N-methylsulfonyl-2-(5-methoxycyclopent-1-en-1-yl)-6-methylanihne. The reaction of N-methylsulfonyl-2-(5-isothiocyanatocyclopent-1-en-1-yl)-6-methylaniline with diethylamine led to the formation of N-methylsulfonyl-2-5-[diethylamino(thioxo)methyl]aminocyclopent-1-en-1-yl}-6-methylanihne which was converted into 5-methyl-4-methylsulfonyl-2,3,3a,4-tetrahydrocyclopenta[b]indole by heating with potassium hydroxide.