(E)-1-(4-trifluoromethylphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one | 173543-23-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-(4-trifluoromethylphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: (E)-1-[4-(trifluoromethyl)phenyl]-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 173543-23-2
• 化学式: C₁₉H₁₇F₃O₄
• 分子量: 366.337
• InChiKey: UIJABVKOSUJSHT-RUDMXATFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzylpentacarbonylmanganese 、 (E)-1-(4-trifluoromethylphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 以 petroleum ether 为溶剂， 以78%的产率得到[[1-(3,4,5-trimethoxyphenyl)-2-(4-trifluoromethylphenylcarbonyl-κO)]ethenyl-κC(1)]tetracarbonylmanganese
  参考文献：
  名称：

  Preparation of cyclomanganated chalcones and their reactions with methyl acrylate and other α, β-unsaturated carbonyl compounds

  摘要：

  Chalcones [(E)-1,3-diarylprop-2-en-1-ones] react with benzyltetracarbonylmanganese under reflux in petroleum spirit to give two types of cyclomanganation products. The first, involving metallation at the alkenyl beta-carbon of the enone, are derivatives of [[1-phenyl-2-phenylcarbonyl-kappa O]ethenyl-kappa C-1]tetracarbonylmanganese, while the second type, manganated at the aryl ring ortho-carbon, are derivatives of [2-[3-phenylprop-2-en-1-onyl-kappa O]phenyl-kappa C-1]tetracarbonylmangane In general, more ''alkene-manganated'' than ''ring-manganated'' product is formed, with the ratio influenced significantly by certain substituents, e.g. a 4-CF3 substituent on the phenyl ring at C3 of the enone strongly promotes ''alkene-manganation''. in some cases there are minor by-products derived from coupling of two chalcone molecules after initial cyclomanganation. The crystal structures are reported for two such products, [2-((1S*,2R*,3S*)-1-hydroxy-1-((E)-2-(2-trifluoromethylphenyl)ethenyl)-3-(2-trifluoromethylphenyl)-6-methoxy-2-indanylcarbonyl- kappa O)-6-methoxyphenyl-kappa C-1]tetracarbonylmanganese and (1S*,4S*,5R*)-5-(4-bromobenzoyl)-1-(4-bromophenyl)-3,4-di-(4-trifluoromethylphenyl)cyclopent-2-en-1-ol.In acetonitrile under reflux, alkene-manganated chalcones react with methyl acrylate (methyl propenoate) to form derivatives of methyl (E)-4,6-diphenyl-6-oxohex-2-enoate and of 5-(2-methoxycarbonylethyl)-3,5-diphenylfuran-2-(5H)-one. The latter butenolides are not formed when the reactions are carried out in carbon tetrachloride, only the former alpha,beta-unsaturated esters. By contrast, in a few reactions studied, acrolein (propenal) and methyl vinyl ketone (but-3-en-2-one) give only the butenolide products when treated with alkene-manganated chalcones in refluxing acetonitrile. An exception is the reaction of methyl vinyl ketone with [[1 -(3,4,5-trimethoxyphenyl)-2-(4-chlorophenylcarbonyl-kappa O)]ethenyl-kappa C-1]tetracarbonylmanganese to form the cyclized product 5-acetyl-1-(4-chlorophenyl)3-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-ol.

  DOI：

  10.1016/0022-328x(95)05488-b
• 作为产物：
  描述：

  4'-三氟甲基苯乙酮 、 3,4,5-三甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以58%的产率得到(E)-1-(4-trifluoromethylphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  The synthesis and effect of fluorinated chalcone derivatives on nitric oxide production

  摘要：

  Dimethoxy- and trimethoxychalcone derivatives, with various patterns of fluorination, were synthesized and evaluated for their influence on nitric oxide production. Some of them, chalcones 1, 5, 7, 10, 11 and 17, inhibited NO production with an IC50 in the submicromolar range; 17 is especially noteworthy because of its potency (IC50 30 nM). These effects were not the consequence of a direct inhibitory action on enzyme activity but the inhibition of enzyme expression. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00317-7

文献信息

• The synthesis and effect of fluorinated chalcone derivatives on nitric oxide production
  作者：Javier Rojas、Miguel Payá、José N Dominguez、M Luisa Ferrándiz

  DOI：10.1016/s0960-894x(02)00317-7

  日期：2002.8

  Dimethoxy- and trimethoxychalcone derivatives, with various patterns of fluorination, were synthesized and evaluated for their influence on nitric oxide production. Some of them, chalcones 1, 5, 7, 10, 11 and 17, inhibited NO production with an IC50 in the submicromolar range; 17 is especially noteworthy because of its potency (IC50 30 nM). These effects were not the consequence of a direct inhibitory action on enzyme activity but the inhibition of enzyme expression. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Preparation of cyclomanganated chalcones and their reactions with methyl acrylate and other α, β-unsaturated carbonyl compounds
  作者：Warren Tully、Lyndsay Main、Brian K. Nicholson

  DOI：10.1016/0022-328x(95)05488-b

  日期：1995.11

  Chalcones [(E)-1,3-diarylprop-2-en-1-ones] react with benzyltetracarbonylmanganese under reflux in petroleum spirit to give two types of cyclomanganation products. The first, involving metallation at the alkenyl beta-carbon of the enone, are derivatives of [[1-phenyl-2-phenylcarbonyl-kappa O]ethenyl-kappa C-1]tetracarbonylmanganese, while the second type, manganated at the aryl ring ortho-carbon, are derivatives of [2-[3-phenylprop-2-en-1-onyl-kappa O]phenyl-kappa C-1]tetracarbonylmangane In general, more ''alkene-manganated'' than ''ring-manganated'' product is formed, with the ratio influenced significantly by certain substituents, e.g. a 4-CF3 substituent on the phenyl ring at C3 of the enone strongly promotes ''alkene-manganation''. in some cases there are minor by-products derived from coupling of two chalcone molecules after initial cyclomanganation. The crystal structures are reported for two such products, [2-((1S*,2R*,3S*)-1-hydroxy-1-((E)-2-(2-trifluoromethylphenyl)ethenyl)-3-(2-trifluoromethylphenyl)-6-methoxy-2-indanylcarbonyl- kappa O)-6-methoxyphenyl-kappa C-1]tetracarbonylmanganese and (1S*,4S*,5R*)-5-(4-bromobenzoyl)-1-(4-bromophenyl)-3,4-di-(4-trifluoromethylphenyl)cyclopent-2-en-1-ol.In acetonitrile under reflux, alkene-manganated chalcones react with methyl acrylate (methyl propenoate) to form derivatives of methyl (E)-4,6-diphenyl-6-oxohex-2-enoate and of 5-(2-methoxycarbonylethyl)-3,5-diphenylfuran-2-(5H)-one. The latter butenolides are not formed when the reactions are carried out in carbon tetrachloride, only the former alpha,beta-unsaturated esters. By contrast, in a few reactions studied, acrolein (propenal) and methyl vinyl ketone (but-3-en-2-one) give only the butenolide products when treated with alkene-manganated chalcones in refluxing acetonitrile. An exception is the reaction of methyl vinyl ketone with [[1 -(3,4,5-trimethoxyphenyl)-2-(4-chlorophenylcarbonyl-kappa O)]ethenyl-kappa C-1]tetracarbonylmanganese to form the cyclized product 5-acetyl-1-(4-chlorophenyl)3-(3,4,5-trimethoxyphenyl)cyclopent-2-en-1-ol.