methyl (E)-3-(4-cyanophenyl)-2-phenylacrylate | 139616-17-4

• 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: methyl (E)-3-(4-cyanophenyl)-2-phenylacrylate
• 英文别名: methyl (E)-3-(4-cyanophenyl)-2-phenylprop-2-enoate
• CAS: 139616-17-4
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: UGAKGIUHVCFNBS-LFIBNONCSA-N

物化性质

• 熔点：
  118.8-119.5 °C
• 沸点：
  431.3±40.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  a-叠氮基-苯乙酸甲酯 、 对氰基溴化苄 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 sodium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以75%的产率得到methyl (E)-3-(4-cyanophenyl)-2-phenylacrylate
  参考文献：
  名称：

  Palladium-Catalyzed Cross Coupling Reaction of Benzyl Bromides with Diazoesters for Stereoselective Synthesis of (E)-α,β-Diarylacrylates

  摘要：

  A Pd-catalyzed cross-coupling reaction of benzyl bromides with alpha-aryldiazoesters is described, and E-alpha,beta-diarylacrylates were obtained in good yields and excellent E-to-Z selectivity (>20:1).

  DOI：

  10.1021/ol8026076

文献信息

• P(NMe₂)₃-Mediated Umpolung Alkylation and Nonylidic Olefination of α-Keto Esters
  作者：Sunewang Rixin Wang、Alexander T. Radosevich

  DOI：10.1021/acs.orglett.5b01784

  日期：2015.8.7

  A commercial phosphorus-based reagent (P(NMe2)(3)) mediates,umpolung alkylation of methyl aroylformates with benzylic and allylic bromides, leading to either Barer-type addition or ylide-free olefination products upon workup. The reaction sequence is initiated, by a two-electron redox addition of the tricoordinate phosphorus reagent with an alpha-keto ester Compound (Kukhtin-Ramirez addition). A mechanistic rationale is offered for the chemoselectivity upon which the success of this nonmetal mediated C-C bond forming strategy is based.
• Palladium-Catalyzed Cross Coupling Reaction of Benzyl Bromides with Diazoesters for Stereoselective Synthesis of (<i>E</i>)-α,β-Diarylacrylates
  作者：Wing-Yiu Yu、Yuk-Tai Tsoi、Zhongyuan Zhou、Albert S. C. Chan

  DOI：10.1021/ol8026076

  日期：2009.1.15

  A Pd-catalyzed cross-coupling reaction of benzyl bromides with alpha-aryldiazoesters is described, and E-alpha,beta-diarylacrylates were obtained in good yields and excellent E-to-Z selectivity (>20:1).