trifluoro-N-(2-phenylacetyl)methanesulfonamide | 174282-49-6

• 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: trifluoro-N-(2-phenylacetyl)methanesulfonamide
• 英文别名: trifluoro-N-(phenylacetyl)methanesulfonamide；2-phenyl-N-(trifluoromethylsulfonyl)acetamide
• CAS: 174282-49-6
• 化学式: C₉H₈F₃NO₃S
• 分子量: 267.229
• InChiKey: ILFOIDHBFPFZMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  trifluoro-N-(2-phenylacetyl)methanesulfonamide 、 苯肼 以 二氯甲烷 为溶剂， 以0.20 g的产率得到苯乙酸苯酰肼
  参考文献：
  名称：

  Reactions of N-sulfinyltrifluoromethanesulfonamide with carboxylic acids

  摘要：

  Phenylacetic, diphenylacetic, salicylic, and cinnamic acids reacted with N-sulfinyltrifluoromethanesulfonamide (CF3SO2NSO) to give the corresponding N-acyltrifluoromethanesulfonamides CF3SO2NHCOR (R = PhCH2, Ph2CH, o-HOC6H4, PhCH=CH). The reaction of N-sulfinyl-trifluoromethanesulfonamide with 3-hydrazinobenzoic acid Occurred at the hydrazino group of the latter with conservation of the carboxy group and without elimination of SO2, and the product was 3-(2-sulfinylhydrazino)benzoic acid OSNNHC6H4CO2H.

  DOI：

  10.1134/s1070428008080022
• 作为产物：
  描述：

  苯乙酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 氯化亚砜 、 三乙胺 作用下， 以 丙酮 为溶剂， 反应 1.25h， 生成 trifluoro-N-(2-phenylacetyl)methanesulfonamide
  参考文献：
  名称：

  Synthesis and Evaluation of N-(Phenylacetyl)trifluoromethanesulfonamides as Anticonvulsant Agents

  摘要：

  A series of N-(phenylacetyl)trifluoromethanesulfonamides (3a-g) was prepared according to the Topliss scheme in order to determine if aryl substitutents would influence anticonvulsant activity. In initial (phase I) screening and quantitative (phase II) evaluation, all seven compounds exhibited significant activity against MES- and scMet-induced seizures. N-(Phenylacetyl)trifluoromethanesulfonamide (3a) was then advanced through five additional testing phases (phases III-VII). Compound 3a displayed good oral bioavailability, low toxicity, and a larger protective index in mice than the prototype drugs, phenytoin, phenobarbital, valproate, and ethosuximide. Additionally, 3a exhibited a longer time to peak effect in all tests and a greater 24-h margin of safety (HD50/ED(50)) than the prototypes. Compound 3a blocked picrotoxin-induced seizures but was ineffective. against seizures induced by bicuculline or strychnine. In vitro receptor binding studies revealed that 3a did not displace [H-3]-labeled gamma-aminobutyric acid or [H-3]-labeled flunitrazepam, and tolerance did not develop during 5-day chronic administration.

  DOI：

  10.1021/jm950761q

文献信息

• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.2, 1.3.3, page 120 - 137
  作者：

  DOI：——

  日期：——
• US3637845
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and Evaluation of <i>N</i>-(Phenylacetyl)trifluoromethanesulfonamides as Anticonvulsant Agents
  作者：Patrick T. Flaherty、Thomas D. Greenwood、Amy L. Manheim、James F. Wolfe

  DOI：10.1021/jm950761q

  日期：1996.1.1

  A series of N-(phenylacetyl)trifluoromethanesulfonamides (3a-g) was prepared according to the Topliss scheme in order to determine if aryl substitutents would influence anticonvulsant activity. In initial (phase I) screening and quantitative (phase II) evaluation, all seven compounds exhibited significant activity against MES- and scMet-induced seizures. N-(Phenylacetyl)trifluoromethanesulfonamide (3a) was then advanced through five additional testing phases (phases III-VII). Compound 3a displayed good oral bioavailability, low toxicity, and a larger protective index in mice than the prototype drugs, phenytoin, phenobarbital, valproate, and ethosuximide. Additionally, 3a exhibited a longer time to peak effect in all tests and a greater 24-h margin of safety (HD50/ED(50)) than the prototypes. Compound 3a blocked picrotoxin-induced seizures but was ineffective. against seizures induced by bicuculline or strychnine. In vitro receptor binding studies revealed that 3a did not displace [H-3]-labeled gamma-aminobutyric acid or [H-3]-labeled flunitrazepam, and tolerance did not develop during 5-day chronic administration.
• Reactions of N-sulfinyltrifluoromethanesulfonamide with carboxylic acids
  作者：B. A. Shainyan、L. L. Tolstikova、A. V. Bel’skikh

  DOI：10.1134/s1070428008080022

  日期：2008.8

  Phenylacetic, diphenylacetic, salicylic, and cinnamic acids reacted with N-sulfinyltrifluoromethanesulfonamide (CF3SO2NSO) to give the corresponding N-acyltrifluoromethanesulfonamides CF3SO2NHCOR (R = PhCH2, Ph2CH, o-HOC6H4, PhCH=CH). The reaction of N-sulfinyl-trifluoromethanesulfonamide with 3-hydrazinobenzoic acid Occurred at the hydrazino group of the latter with conservation of the carboxy group and without elimination of SO2, and the product was 3-(2-sulfinylhydrazino)benzoic acid OSNNHC6H4CO2H.