(E)-1-methyl-4-(3,3,3-trifluoro-2-phenylprop-1-enyl)benzene | 1268607-02-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-1-methyl-4-(3,3,3-trifluoro-2-phenylprop-1-enyl)benzene
• 英文别名: (E)-1-(4-methylphenyl)-2-phenyl-3,3,3-trifluoroprop-1-ene；(E)-1-(4-methylphenyl)-2-phenyl-3,3,3-trifluoropropene；1-methyl-4-[(E)-3,3,3-trifluoro-2-phenylprop-1-enyl]benzene
• CAS: 1268607-02-8
• 化学式: C₁₆H₁₃F₃
• 分子量: 262.274
• InChiKey: CJMFBRZLYVZZSL-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(4-methoxyphenyl)-2-(p-tolyl)ethan-1-one 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydride 、 lithium chloride 作用下， 以 甲基叔丁基醚 、 甲苯 为溶剂， 反应 0.02h， 生成 (E)-1-methyl-4-(3,3,3-trifluoro-2-phenylprop-1-enyl)benzene
  参考文献：
  名称：

  （Z）-α-三氟甲基烯基三氟甲磺酸酯的合成：一种用于三氟甲基化物种的支架

  摘要：

  描述了一种合成（Z）-选择性α-三氟甲基烯基三氟甲磺酸酯的有效方法。作为重要的氟化结构单元，已成功地用于合成各种三氟甲基衍生物，例如二芳基乙烯，烯炔，炔烃和苯并呋喃。

  DOI：

  10.1021/acs.joc.6b00855

文献信息

• One-Pot Multistep Synthesis of Trisubstituted Alkenes from N-Tosylhydrazones and Alcohols
  作者：Yunyang Wei、Qiang Sha

  DOI：10.1055/s-0034-1378231

  日期：——

  Abstract A one-pot procedure for the synthesis of trisubstituted alkenes from N-tosylhydrazones and alcohols is reported. This procedure combines the aerobic oxidation reaction and Wittig reaction in one pot, which avoids using of environmentally toxic oxidants and isolation of the intermediates. The simple procedure makes it very attractive for the synthesis of trisubstituted alkenes when alcohols are used

  摘要 据报道一锅法由N-甲苯磺酰基hydr和醇合成三取代的烯烃。该程序将好氧氧化反应和Wittig反应合二为一，避免了使用对环境有害的氧化剂和中间体的分离。当将醇用作起始原料时，简单的方法使其对于三取代烯烃的合成非常有吸引力。以中等至良好的收率（高达84％）和良好的E-选择性（高达99％）获得了各种三取代的烯烃以及三氟甲基取代的烯烃。 据报道一锅法由N-甲苯磺酰基hydr和醇合成三取代的烯烃。该程序将好氧氧化反应和Wittig反应合二为一，避免了使用对环境有害的氧化剂和中间体的分离。当将醇用作起始原料时，简单的方法使其对于三取代烯烃的合成非常有吸引力。以中等至良好的收率（高达84％）和良好的E-选择性（高达99％）获得了各种三取代的烯烃以及三氟甲基取代的烯烃。
• Copper(I)-Catalyzed Wittig Olefination Reactions of<i>N</i>-Tosylhydrazones with Trifluoromethylketones
  作者：Qiang Sha、Yunyang Wei

  DOI：10.1002/cctc.201300583

  日期：2014.1

  iodide‐catalyzed Wittig olefination reactions of N‐tosylhydrazones with trifluoromethylketones are reported. This procedure provides an efficient method for the synthesis of various trifluoromethyl‐substituted alkenes in moderate to good yields (up to 89 % yield) and good stereoselectivity (up to 93 % E‐selectivity). To the best of our knowledge, it is the first report of a Wittig reaction of N‐tosylhydrazones

  报道了N-甲苯磺酰hydr与三氟甲基酮的碘化亚铜催化的Wittig烯化反应。该方法为中等至良好的收率（高达89％的收率）和良好的立体选择性（高达93％的E选择性）合成各种三氟甲基取代的烯烃提供了一种有效的方法。据我们所知，这是N-甲苯磺酰azo与酮发生维蒂希反应的首次报道。
• Wittig reaction with ion-supported Ph3P
  作者：Naoya Shimojuh、Yumi Imura、Katsuhiko Moriyama、Hideo Togo

  DOI：10.1016/j.tet.2010.11.111

  日期：2011.2

  Ion-supported Ph3P, 4-(diphenylphosphino)benzyltrimethylammonium bromide A and N-methyl-N-[4(diphenylphosphino)benzyl]pyrrolidinium bromide B, were used for the Wittig reaction. Ion-supported phosphonium salts A1 and B1, which were prepared from the reactions of ion-supported Ph3P A and B with ethyl bromoacetate, respectively, reacted with aromatic and aliphatic aldehydes in the presence of K2CO3 to give the corresponding alpha,beta-unsaturated ethyl esters in good yields with high purity by simple filtration of the reaction mixture and subsequent removal of the solvent from the filtrate. Similarly, ion-supported phosphonium salts A2 and B2, which were prepared from the reactions of ion-supported Ph3P A and B with p-methylbenzyl bromide, respectively, reacted with aromatic and aliphatic aldehydes in the presence of NaH to provide the corresponding p-methylstyrene derivatives in good yields with high purity by simple filtration of the reaction mixture and the subsequent removal of the solvent from the filtrate. In both reactions, the co-product, ion-supported Ph3PO, could be obtained quantitatively by simple filtration, and was converted into the corresponding ion-supported Ph3P A and B again in high yields using dimethyl sulfate, followed by the reduction with LiAlH4. Recovered and regenerated ion-supported Ph3P A and B could be reused for the same Wittig reaction while maintaining good yields of ethyl (E)-3-(4'-chlorophenyl)-2-propenoate and 1 -(4'-chlorophenyl)-2-(4 ''-methylphenyl)ethene with high purity by simple filtration and removal of the solvent from the filtrate. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of (<i>Z</i>)-α-Trifluoromethyl Alkenyl Triflate: A Scaffold for Diverse Trifluoromethylated Species
  作者：Yilong Zhao、Yuhan Zhou、Juan Liu、Dongmei Yang、Liang Tao、Yang Liu、Xiaoliang Dong、Jianhui Liu、Jingping Qu

  DOI：10.1021/acs.joc.6b00855

  日期：2016.6.3

  An efficient method for the synthesis of (Z)-selective α-trifluoromethyl alkenyl triflates is described. As an important fluorinated building block, it is utilized successfully for the synthesis of various trifluoromethyl derivatives such as diarylethylenes, enynes, alkynes, and benzofurans.

  描述了一种合成（Z）-选择性α-三氟甲基烯基三氟甲磺酸酯的有效方法。作为重要的氟化结构单元，已成功地用于合成各种三氟甲基衍生物，例如二芳基乙烯，烯炔，炔烃和苯并呋喃。