ethyl 3-phenyl-2-(p-tolyl)acrylate | 1020074-02-5

• 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: ethyl 3-phenyl-2-(p-tolyl)acrylate
• 英文别名: ethyl (Z)-2-(4-methylphenyl)-3-phenylprop-2-enoate
• CAS: 1020074-02-5
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: KHAFLRDMOVFNOQ-LGMDPLHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(苯乙炔基)苯甲酸乙酯 、 4-methylbenzenediazonium tetrafluoroborate 在 palladium diacetate 、 三苯基硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以44%的产率得到ethyl 3-phenyl-2-(p-tolyl)acrylate
  参考文献：
  名称：

  Palladium-Catalyzed Hydroarylation of Alkynes with Arenediazonium Salts

  摘要：

  The palladium-catalyzed hydroarylation of arenediazonium tetrafluoroborates with alkynes in the presence of triphenylsilane affords stereoselectively hydroarylation products in moderate to high yields. The reaction tolerates a variety of substituents including keto, ester, cyano, and nitro groups and can be performed as a one-pot procedure generating the arenediazonium salt in situ. With ethyl phenylpropynoate as the starting alkyne, the hydroarylation affords ethyl (2)-2-arylcinnamates stereo- and regioselectively.

  DOI：

  10.1021/ol800266e

文献信息

• Palladium-catalyzed cross-coupling reaction of sulfoxonium ylides and benzyl bromides by carbene migratory insertion
  作者：Kaichuan Yan、Maoyao He、Jianglian Li、Hua He、Ruizhi Lai、Yi Luo、Li Guo、Yong Wu

  DOI：10.1039/d0cc06236g

  日期：——

  A palladium-catalyzed cross-coupling reaction of sulfoxonium ylides and benzyl bromides has been developed, which has potential safety advantages over previous carbene coupling reactions using either diazo compounds or their in situ precursors. This reaction affords polysubstituted olefins, and features good substrate tolerance and is suitable for late-stage modification of biologically active molecules

  已经开发了亚砜基yl和苄基溴的钯催化交叉偶联反应，与使用重氮化合物或其原位前体的先前卡宾偶联反应相比，它具有潜在的安全优势。该反应提供了多取代的烯烃，并且具有良好的底物耐受性，并且适合于生物活性分子的后期修饰。钯-卡宾迁移插入可能参与了该偶联反应。
• Palladium-Catalyzed Hydroarylation of Alkynes with Arenediazonium Salts
  作者：Sandro Cacchi、Giancarlo Fabrizi、Antonella Goggiamani、Daniela Persiani

  DOI：10.1021/ol800266e

  日期：2008.4.1

  The palladium-catalyzed hydroarylation of arenediazonium tetrafluoroborates with alkynes in the presence of triphenylsilane affords stereoselectively hydroarylation products in moderate to high yields. The reaction tolerates a variety of substituents including keto, ester, cyano, and nitro groups and can be performed as a one-pot procedure generating the arenediazonium salt in situ. With ethyl phenylpropynoate as the starting alkyne, the hydroarylation affords ethyl (2)-2-arylcinnamates stereo- and regioselectively.