2-benzyl-3-phenylacrylic acid methyl ester

• 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: 2-benzyl-3-phenylacrylic acid methyl ester
• 英文别名: Methyl 2-benzyl-3-phenylprop-2-enoate
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: RZNVZSGZYXHKNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  methyl-(2-chloromethyl)-3-phenylacrylate 、 三苯基铋 在 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 1.0h， 以76%的产率得到2-benzyl-3-phenylacrylic acid methyl ester
  参考文献：
  名称：

  使用Baylis-Hillman加合物的溴化物和氯化物衍生物与三芳基铋作为原子有效的多偶联亲核试剂，使用Pd（0）催化偶联

  摘要：

  事实证明，在钯催化的条件下，Baylis-Hillman加合物的溴化物和氯化物衍生物可与三芳基铋有效反应，从而以高收率提供烯丙基芳基化产物。在这些反应中，三芳基铋已以低于化学计量的量用作多偶联和原子有效的亲核试剂。发现烯丙基溴和氯化物的反应性都容易并且在与三芳基铋的偶联中同样有效。

  DOI：

  10.1016/j.tet.2010.03.020

文献信息

• Ligand-Free Reusable Palladium-Catalyzed Heck-Type Coupling Reactions of Hypervalent Iodine Reagents under Mild Conditions
  作者：Xiaoming Qu、Peng Sun、Tingyi Li、Jincheng Mao

  DOI：10.1002/adsc.201100008

  日期：2011.5.9

  Highly effective palladium‐catalyzed Heck‐type couplings of hypervalent iodine reagents are reported for the first time. It is noteworthy that such reactions could be carried out in the absence of ligand at 40 °C and the catalytic system could be easily reused for five times.

  首次报道了高价碘试剂的高效钯催化的Heck型偶联。值得注意的是，此类反应可在不存在配体的情况下于40°C进行，催化体系可轻松重复使用五次。
• Fe³⁺-K-10 Montmorillonite Clay Catalyzed Friedel–Crafts Reaction of Unactivated Baylis–Hillman Adducts: An Efficient Stereoselective Synthesis of Trisubstituted Alkenes Containing a Benzyl Substituent
  作者：Biswanath Das、Anjoy Majhi、Joydeep Banerjee、Nikhil Chowdhury、Katta Venkateswarlu

  DOI：10.1246/cl.2005.1492

  日期：2005.11

  The stereoselective synthesis of trisubstituted alkenes containing a benzyl substituent has been achieved by employing Friedel-Craft reaction of aromatic compounds with unactivated Baylis-Hillman adducts in the presence of Fe 3 + -K-10 montmorillonite clay as a heterogeneous catalyst. The catalyst can be recovered and reused.

  在 Fe 3 + -K-10 蒙脱石粘土作为非均相催化剂存在下，通过使用芳族化合物与未活化的 Baylis-Hillman 加合物的 Friedel-Craft 反应，实现了含有苄基取代基的三取代烯烃的立体选择性合成。催化剂可以回收再利用。
• Copper-Catalyzed α-Benzylation of Enones via Radical-Triggered Oxidative Coupling of Two C–H Bonds
  作者：Guiping Qin、Xiangning Chen、Lei Yang、Hanmin Huang

  DOI：10.1021/acscatal.5b00310

  日期：2015.5.1

  A novel copper(II)-catalyzed, regioselective C-H benzylation of enones with toluenes via radical triggered oxidative coupling has been developed. A series of enones and toluenes with different substituents were successfully incorporated, providing a wide range of alpha-benzylated enones with TBP as oxidant by cleavage of C(sp(3)) H bond and C(sp(2)) H bond. Preliminary mechanistic study reveals a benzylic carbon radical is generated, and regioselectively reacts with enones to deliver the corresponding products.
• Thianthrenation-promoted photoinduced alkene difunctionalization and aryl allylation with Morita–Baylis–Hillman adducts
  作者：Biplab Mondal、Ayan Chatterjee、Nitis Chandra Saha、Manoranjan Jana、Jaideep Saha

  DOI：10.1039/d4cc01792g

  日期：——

  An organophotoredox-catalyzed alkoxyallylation of feed-stock olefins, through thianthrenation using a Morita–Baylis–Hillman adduct as an allylating agent, is described.