(E)-1-(4-bromophenyl)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one

• 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-bromophenyl)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one
• 英文别名: (E)-1-(4-bromophenyl)-3-(4-trifluoromethylphenyl)prop-2-en-1-one；(E)-1-(4-bromophenyl)-3-[4-(trifluoromethyl)phenyl]prop-2-en-1-one
• 化学式: C₁₆H₁₀BrF₃O
• 分子量: 355.154
• InChiKey: MFZOSZLIRQWDQE-XCVCLJGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-bromophenyl)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one 在 benzylpentacarbonylmanganese 作用下， 以 Petroleum ether 为溶剂， 反应 5.0h， 以10%的产率得到(1S^*,4S^*,5R^*)-5-(4-bromobenzoyl)-1-(4-bromophenyl)-3,4-di-(4-trifluoromethylphenyl)cyclopent-2-en-1-ol
  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：

  对三氟甲基苯甲醛 、 4-溴苯乙酮 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 (E)-1-(4-bromophenyl)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  合成、晶体结构、Hirshfeld 表面分析、光谱表征、DFT 和 MD 方法的反应性研究以及新型查耳酮衍生物的分子对接研究

  摘要：

  摘要 本研究合成了标题化合物(E)-1-(4-溴苯基)-3-(4-(三氟甲基)苯基)prop-2-en-1-one晶体 X 射线衍射。该化合物在P21/c空间群中以单斜晶系结晶，晶胞参数a = 16.7629 (12) A, b = 13.9681 (10) A, c = 5.8740 (4) A, β = 96.3860 (12)°和Z = 4. Hirshfeld 表面分析显示分子结构以 H⋯H、C⋯H/H⋯C、Br⋯F/F⋯Br 和 F⋯F 接触为主。借助密度泛函理论 (DFT) 计算和势能分布 (PED) 分析详细记录和解释 FT-IR 光谱。平均局部电离能 (ALIE) 和 Fukui 函数已被用作量子分子描述符来定位从反应性方面可能很重要的分子位点。降解特性已通过计算氢提取和其余单非环键的键解离能 (BDE) 进行评估，同时使用分子动力学 (MD) 模拟来计算径向分布函数并确定

  DOI：

  10.1016/j.molstruc.2017.01.080

文献信息

• A Novel Reaction of the “Huisgen Zwitterion” with Chalcones and Dienones: An Efficient Strategy for the Synthesis of Pyrazoline and Pyrazolopyridazine Derivatives
  作者：Vijay Nair、Smitha C. Mathew、Akkattu T. Biju、Eringathodi Suresh

  DOI：10.1002/anie.200604025

  日期：2007.3.12
• 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.
• Synthesis, crystal structure, Hirshfeld surface analysis, spectroscopic characterization, reactivity study by DFT and MD approaches and molecular docking study of a novel chalcone derivative
  作者：Suhana Arshad、Renjith Raveendran Pillai、Dian Alwani Zainuri、Nuridayanti Che Khalib、Ibrahim Abdul Razak、Stevan Armaković、Sanja J. Armaković、C. Yohannan Panicker、C. Van Alsenoy

  DOI：10.1016/j.molstruc.2017.01.080

  日期：2017.5

  molecular structure is dominated by H⋯H, C⋯H/H⋯C, Br⋯F/F⋯Br and F⋯F contacts. The FT-IR spectrum was recorded and interpreted in details with the aid of Density Functional Theory (DFT) calculations and Potential Energy Distribution (PED) analysis. Average local ionization energies (ALIE) and Fukui functions have been used as quantum-molecular descriptors to locate the molecule sites that could be of

  摘要 本研究合成了标题化合物(E)-1-(4-溴苯基)-3-(4-(三氟甲基)苯基)prop-2-en-1-one晶体 X 射线衍射。该化合物在P21/c空间群中以单斜晶系结晶，晶胞参数a = 16.7629 (12) A, b = 13.9681 (10) A, c = 5.8740 (4) A, β = 96.3860 (12)°和Z = 4. Hirshfeld 表面分析显示分子结构以 H⋯H、C⋯H/H⋯C、Br⋯F/F⋯Br 和 F⋯F 接触为主。借助密度泛函理论 (DFT) 计算和势能分布 (PED) 分析详细记录和解释 FT-IR 光谱。平均局部电离能 (ALIE) 和 Fukui 函数已被用作量子分子描述符来定位从反应性方面可能很重要的分子位点。降解特性已通过计算氢提取和其余单非环键的键解离能 (BDE) 进行评估，同时使用分子动力学 (MD) 模拟来计算径向分布函数并确定