N-(2-Cyclopent-1-enyl-phenyl)-methanesulfonamide | 524931-13-3

• 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-(2-Cyclopent-1-enyl-phenyl)-methanesulfonamide
• 英文别名: Methanesulfonamide, N-[2-(1-cyclopenten-1-yl)phenyl]-；N-[2-(cyclopenten-1-yl)phenyl]methanesulfonamide
• CAS: 524931-13-3
• 化学式: C₁₂H₁₅NO₂S
• 分子量: 237.323
• InChiKey: CHHOUCLUHPZPKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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-(2-Cyclopent-1-enyl-phenyl)-methanesulfonamide 在 N-溴代丁二酰亚胺(NBS) 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以84%的产率得到N-mesyl-2-(2-bromo-1-cyclopenten-1-yl)aniline
  参考文献：
  名称：

  Reactions of N-and C-Alkenylanilines: VII. Synthesis of Indole Heterocycles from Products of Reaction between N-Mesyl-2-(1-alken-1-yl)anilines and Halogens

  摘要：

  N-美克基-2-(1-甲基-1-丁烯基)-6-甲基苯胺与Br2反应生成N-美克基-2-(3-溴-1-戊烯-2-基)苯胺，随后在氨气或胺的处理下发生环化，生成N-美克基-7-甲基-3-亚甲基-2-乙基吲哚。N-美克基-2-(1-甲基-1-丁烯-1-基)-4-甲基-和2-(1-甲基-1-丁烯-1-基)苯胺与Br2反应生成相应的N-美克基-2-(2-溴-1-甲基-1-丁烯-1-基)苯胺。在相似的条件下，N-托索基-2-(1-环己烯-1-基)苯胺被转化为N-托索基-2-(6-溴-1-环己烯-1-基)苯胺，该化合物在氨的处理下生成N-托索基-1,2,3,9a-四氢吲哚。N-美克基-1,2,3,9a-四氢吲哚与CuBr2在甲醇中反应生成N-美克基-4-甲氧基-1,2,3,4-四氢吲哚。N-美克基-6-甲基-2-(1-环戊烯-1-基)苯胺在NaHCO3存在下与Br2反应被氧化为相应的环戊酮，而与NBS反应则生成N-美克基-2-(2-溴-1-环戊烯-1-基)苯胺。

  DOI：

  10.1007/s11178-005-0231-x

文献信息

• ——
  作者：R. R. Gataullin、M. F. Nasyrov、I. B. Abdrakhmanov、G. A. Tolstikov

  DOI：10.1023/a:1022572909355

  日期：——

  Heterocyclic compounds of the 4H-3,1-benzoxazine and cyclopenta[b]indole series were synthesized by oxydation of N-acyl derivatives of 2-(1-alkenyl)anilines with hydrogen peroxide. The structure of the oxidation products is determined by the reaction conditions, substituent in the ortho-position of the aromatic ring, protecting group, and alkenyl radical structure.
• Reactions of N-and C-Alkenylanilines: VII. Synthesis of Indole Heterocycles from Products of Reaction between N-Mesyl-2-(1-alken-1-yl)anilines and Halogens
  作者：R. R. Gataullin、A. M. Sotnikov、L. V. Spirikhin、I. B. Abdrakhmanov

  DOI：10.1007/s11178-005-0231-x

  日期：2005.5

  N-Mesyl-2-(1-methyl-1-butenyl)-6-methylaniline reacted with Br2 to afford N-mesyl-2-(3-bromo-1-penten-2-yl)aniline that under treatment with NH3 or amines underwent cyclization into N-mesyl-7-methyl-3-methylene-2-ethylindoline. The reaction of N-mesyl-2-(1-methyl-1-buten-1-yl)-4-methyl- and 2-(1-methyl-1-buten-1-yl)aniline with Br2 gave rise to the corresponding N-mesyl-2-(2-bromo-1-methyl-1-buten-1-yl)anilines. Under the similar conditions N-tosyl-2-(1-cyclohexen-1-yl)aniline was converted into N-tosyl-2-(6-bromo-1-cyclohexen-1-yl)aniline that under treatment with NH3 furnished N-tosyl-1,2,3,9a-tetrahydrocarbazole. The reaction of N-mesyl-1,2,3,9a-tetrahydrocarbazole with CuBr2 in MeOH afforded N-mesyl-4-methoxy-1,2,3,4-tetrahydrocarbazole. N-Mesyl-6-methyl-2-(1-cyclopenten-1-yl)aniline in reaction with Br2 in the presence of NaHCO3 was oxidized into the corresponding cyclopentenone, and with NBS it gave N-mesyl-2-(2-bromo-1-cyclopenten-1-yl)aniline.

  N-美克基-2-(1-甲基-1-丁烯基)-6-甲基苯胺与Br2反应生成N-美克基-2-(3-溴-1-戊烯-2-基)苯胺，随后在氨气或胺的处理下发生环化，生成N-美克基-7-甲基-3-亚甲基-2-乙基吲哚。N-美克基-2-(1-甲基-1-丁烯-1-基)-4-甲基-和2-(1-甲基-1-丁烯-1-基)苯胺与Br2反应生成相应的N-美克基-2-(2-溴-1-甲基-1-丁烯-1-基)苯胺。在相似的条件下，N-托索基-2-(1-环己烯-1-基)苯胺被转化为N-托索基-2-(6-溴-1-环己烯-1-基)苯胺，该化合物在氨的处理下生成N-托索基-1,2,3,9a-四氢吲哚。N-美克基-1,2,3,9a-四氢吲哚与CuBr2在甲醇中反应生成N-美克基-4-甲氧基-1,2,3,4-四氢吲哚。N-美克基-6-甲基-2-(1-环戊烯-1-基)苯胺在NaHCO3存在下与Br2反应被氧化为相应的环戊酮，而与NBS反应则生成N-美克基-2-(2-溴-1-环戊烯-1-基)苯胺。