(E)-2-methyl-3-[3-(trifluoromethyl)phenyl]prop-2-enoyl chloride | 344557-45-5

• 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]prop-2-enoyl chloride
• CAS: 344557-45-5
• 化学式: C₁₁H₈ClF₃O
• 分子量: 248.632
• InChiKey: MNPKRXSFSIFULN-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-2-methyl-3-[3-(trifluoromethyl)phenyl]prop-2-enoyl chloride 以 乙醇 、 苯 为溶剂， 反应 62.0h， 生成 (Z)-N-cyclopropyl-α-methyl-m-(trifluoromethyl)cinnamamide
  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
• 作为产物：
  描述：

  3-Hydroxy-2-methyl-3-(3-trifluoromethyl-phenyl)-propionic acid ethyl ester 在 氢氧化钾 、 草酰氯 、 phosphorus pentoxide 、 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]prop-2-enoyl chloride
  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

• Sleep-inducing N-alkyl-5-[m-(trifluoromethyl)phenyl]-5-hydroxy-2-pyrrolidinones and N-alkyl-3-(trifluoromethyl)cinnamamides
  作者：William J. Houlihan、John H. Gogerty、Eileen A. Ryan、Gemma Schmitt

  DOI：10.1021/jm00379a007

  日期：1985.1

  A series of N-alkyl-3-[m-(trifluoromethyl)phenyl]-5-hydroxy-2-pyrrolidinones and N-alkyl-3-(trifluoromethyl)-cinnamamides were prepared and screened in a series of tests designed to detect potential sleep inducers. The more active members of the series were evaluated for their ability to induce sleep in Cebus monkeys. The most active compound, N-methyl-5-[m-(trifluoromethyl)phenyl]-5-hydroxy-2-pyrrolidinone, was equal to methaqualone.
• 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：——
• HOULIHAN, W.;GOGERTY, J. H.;RYAN, E. A.;SCHMITT, G., J. MED. CHEM., 1985, 28, N 1, 28-31
  作者：HOULIHAN, W.、GOGERTY, J. H.、RYAN, E. A.、SCHMITT, G.

  DOI：——

  日期：——