7-methyl-3-(trifluoromethyl)benzothiophene | 87924-84-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 7-methyl-3-(trifluoromethyl)benzothiophene
• 英文别名: 7-Methyl-3-trifluoromethylbenzo[b]thiophene；Benzo[b]thiophene, 7-methyl-3-(trifluoromethyl)-；7-methyl-3-(trifluoromethyl)-1-benzothiophene
• CAS: 87924-84-3
• 化学式: C₁₀H₇F₃S
• 分子量: 216.227
• InChiKey: XNJVYPQSTURVBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-methyl-3-(trifluoromethyl)benzothiophene 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and structure-activity relationships of benzo[b]thienylallylamine antimycotics

  摘要：

  Benzo[b]thiophene analouges of the allylamine antimycotic terbinafine (2) bearing the side chain at various positions and optionally substituted by halogen have been prepared and their antifungal activity studied. Derivatives bearing the side chain at positions 3, 4, or 7 are bioequivalents of 2. Compounds containing the allylamine side chain at position 7, with a further substituent at position 3, showed significantly enhanced activity against Candida albicans, an effect which appears to be specifically linked only to this particular substitution pattern. 3-Chloro-7-benzo[b]thienyl derivative 7m was found to be the most potent allylamine antimycotic identified so far. In general, substituted benzo[b]thiophenes can be used not only as potential equivalents of naphthalene in bioactive compounds but also as a tool to selectively modify biological activities.

  DOI：

  10.1021/jm00105a011
• 作为产物：
  描述：

  3-bromo-7-methylbenzo(b)thiophene 、 sodium 2,2,2-trifluoroacetate 在 N-甲基吡咯烷酮 、 copper(l) iodide 作用下， 反应 2.0h， 以54%的产率得到7-methyl-3-(trifluoromethyl)benzothiophene
  参考文献：
  名称：

  Synthesis and structure-activity relationships of benzo[b]thienylallylamine antimycotics

  摘要：

  Benzo[b]thiophene analouges of the allylamine antimycotic terbinafine (2) bearing the side chain at various positions and optionally substituted by halogen have been prepared and their antifungal activity studied. Derivatives bearing the side chain at positions 3, 4, or 7 are bioequivalents of 2. Compounds containing the allylamine side chain at position 7, with a further substituent at position 3, showed significantly enhanced activity against Candida albicans, an effect which appears to be specifically linked only to this particular substitution pattern. 3-Chloro-7-benzo[b]thienyl derivative 7m was found to be the most potent allylamine antimycotic identified so far. In general, substituted benzo[b]thiophenes can be used not only as potential equivalents of naphthalene in bioactive compounds but also as a tool to selectively modify biological activities.

  DOI：

  10.1021/jm00105a011

文献信息

• Benzothienylallylamines processes for their production and their use as
  申请人：Sandoz Ltd.

  公开号：US04737516A1

  公开（公告）日：1988-04-12

  Benzothienyldialkylallylamines wherein the amine side chain is attached to the ring via an alkyl radical and is either in 4-, 5-, 6- or 7-position or if not bears tertiary alkylethynyl or alkenylethynyl as its terminal group, which are useful, in particular, as anti-mycotic agents.

  苯并噻吩基二烷基烯丙胺，其中胺侧链通过烷基基团连接到环上，位于4-、5-、6-或7-位置，或者如果不是，则具有三级烷基乙炔基或烯丙基乙炔基作为其末端基团，特别适用于作为抗真菌剂。
• NUSSBAUMER, PETER;PETRANYI, GABOR;STUTZ, ANTON, J. MED. CHEM., 34,(1991) N, C. 65-73
  作者：NUSSBAUMER, PETER、PETRANYI, GABOR、STUTZ, ANTON

  DOI：——

  日期：——
• US4737516A
  申请人：——

  公开号：US4737516A

  公开（公告）日：1988-04-12