1-methyl-4-((3E)-4-phenylbuta-1,3-dien-1-yl)benzene | 57668-27-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-methyl-4-((3E)-4-phenylbuta-1,3-dien-1-yl)benzene
• 英文别名: cis,trans-1-(4-Methylphenyl)-4-phenylbutadien；(1Z,3E)-1-(4-methylphenyl)-4-phenyl-1,3-butadiene；1-methyl-4-[(1Z,3E)-4-phenylbuta-1,3-dienyl]benzene
• CAS: 57668-27-6
• 化学式: C₁₇H₁₆
• 分子量: 220.314
• InChiKey: HWOHNKOFLQZHJO-POQLCMLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  17
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  反式肉桂醛 、 在 sodium amide 作用下， 以 乙二醇二甲醚 为溶剂， 反应 25.0h， 生成 1-methyl-4-((3E)-4-phenylbuta-1,3-dien-1-yl)benzene 、 (E,E)-1-(4-methylphenyl)-4-phenylbuta-1,3-diene
  参考文献：
  名称：

  Wittig reaction with ion-supported Ph3P

  摘要：

  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.

  DOI：

  10.1016/j.tet.2010.11.111

文献信息

• Phosphorus-Recycling Wittig Reaction: Design and Facile Synthesis of a Fluorous Phosphine and Its Reusable Process in the Wittig Reaction
  作者：Yuki Yamamoto、Shin-ichi Kawaguchi、Misaki Nishimura、Yuki Sato、Yoshihisa Shimada、Akihiro Tabuchi、Akihiro Nomoto、Akiya Ogawa

  DOI：10.1021/acs.joc.0c01926

  日期：2020.11.20

  phosphorus sources can be recycled using the appropriate fluorous phosphine in the Wittig reaction. The designed fluorous phosphine, which has an ethylene spacer between its phosphorus atom and the perfluoroalkyl group, was synthesized from air-stable phosphine reagents. The synthesized phosphine can be used for the Wittig reaction process to obtain various alkenes in adequate yields and stereoselectivity

  这项研究表明，可以在Wittig反应中使用适当的氟膦来回收磷源。由空气稳定的膦试剂合成了设计的氟膦，该磷膦在其磷原子和全氟烷基之间具有一个乙烯间隔基。合成的膦可用于Wittig反应过程，以足够的收率和立体选择性获得各种烯烃。使用氟双相体系从反应混合物中提取伴随形成的氟氧化膦。通过用二异丁基氢化铝还原氟代膦氧化物来再生氟代膦。最后，进行了一系列的克级磷回收过程，包括Wittig反应，分离，还原和再利用。