(E)-2-Methyl-3-(3-trifluoromethyl-phenyl)-but-2-enoic acid allylamide | 77302-21-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-2-Methyl-3-(3-trifluoromethyl-phenyl)-but-2-enoic acid allylamide
• 英文别名: trans-N-Allyl-alpha,beta-dimethyl-m-trifluoromethylcinnamamide；(E)-2-methyl-N-prop-2-enyl-3-[3-(trifluoromethyl)phenyl]but-2-enamide
• CAS: 77302-21-7
• 化学式: C₁₅H₁₆F₃NO
• 分子量: 283.293
• InChiKey: MQNUGPTXEQZQSN-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (Z)-2-Methyl-3-(3-trifluoromethyl-phenyl)-but-2-enoic acid ethyl ester 在 氢氧化钾 、 草酰氯 、 calcium carbonate 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 44.0h， 生成 (E)-2-Methyl-3-(3-trifluoromethyl-phenyl)-but-2-enoic acid allylamide
  参考文献：
  名称：

  Structure-activity relationship in cinnamamides. 3. Synthesis and anticonvulsant activity evaluation of some derivatives of (E)- and (Z)-m-(trifluoromethyl)cinnamamide

  摘要：

  The (E)- and (Z)-m-(trifluoromethyl)-alpha, beta-dimethylcinnamamides and some of their N-alkyl derivatives were prepared and pharmacologically tested as anticonvulsant agents in order to verify if a ring substituent, like the m-CF3 group, different from a halogen but possessing the same electronic effect could lead to equally active compounds. Some (E)-m-(trifluoromethyl)-alpha-methyl- and -non-methyl-substituted-cinnamamides were also prepared and tested. In the alpha, beta-dimethyl series the results show that the m-CF3 group leads to products more active than the ones unsubstituted on the phenyl ring but still less active than the p-halogen-substituted compounds previously studied. In the alpha-methyl and non-methyl-substituted series, the trend shows the m-CF3 group being able to produce less toxic and, in some cases, more active products than the previously studied amides.

  DOI：

  10.1021/jm00137a010

文献信息

• BALSAMO A.; CROTTI P.; LAPUCCI A.; MACCHIA B.; MACCHIA F.; CUTTICA A.; PA+, J. MED. CHEM., 1981, 24, NO 5, 525-532
  作者：BALSAMO A.、 CROTTI P.、 LAPUCCI A.、 MACCHIA B.、 MACCHIA F.、 CUTTICA A.、 PA+

  DOI：——

  日期：——
• Structure-activity relationship in cinnamamides. 3. Synthesis and anticonvulsant activity evaluation of some derivatives of (E)- and (Z)-m-(trifluoromethyl)cinnamamide
  作者：A. Balsamo、P. Crotti、A. Lapucci、B. Macchia、F. Macchia、A. Cuttica、N. Passerini

  DOI：10.1021/jm00137a010

  日期：1981.5

  The (E)- and (Z)-m-(trifluoromethyl)-alpha, beta-dimethylcinnamamides and some of their N-alkyl derivatives were prepared and pharmacologically tested as anticonvulsant agents in order to verify if a ring substituent, like the m-CF3 group, different from a halogen but possessing the same electronic effect could lead to equally active compounds. Some (E)-m-(trifluoromethyl)-alpha-methyl- and -non-methyl-substituted-cinnamamides were also prepared and tested. In the alpha, beta-dimethyl series the results show that the m-CF3 group leads to products more active than the ones unsubstituted on the phenyl ring but still less active than the p-halogen-substituted compounds previously studied. In the alpha-methyl and non-methyl-substituted series, the trend shows the m-CF3 group being able to produce less toxic and, in some cases, more active products than the previously studied amides.