(E)-2-(4-chlorobenzyl)-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: (E)-2-(4-chlorobenzyl)-3-phenylacrylic acid methyl ester
• 英文别名: 2-(4-chlorobenzyl)-3-phenylacrylic acid methyl ester；methyl (E)-2-[(4-chlorophenyl)methyl]-3-phenylprop-2-enoate
• 化学式: C₁₇H₁₅ClO₂
• 分子量: 286.758
• InChiKey: LIZDGRRLEQCQSR-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  氯代苯基三乙氧基硅烷 、 2-[乙酰氧基(苯基)甲基]丙烯酸甲酯 在 tris(dibenzylideneacetone)dipalladium (0) 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以92%的产率得到(E)-2-(4-chlorobenzyl)-3-phenylacrylic acid methyl ester
  参考文献：
  名称：

  Palladium-Catalyzed Cross-Coupling of Baylis−Hillman Acetate Adducts with Organosilanes

  摘要：

  A cross-coupling reaction between acetates of Baylis-Hillman adducts and organosilanes is described. A nonconventional solvent poly(ethylene glycol) (PEG) is used as the reaction medium.

  DOI：

  10.1021/jo051177k

文献信息

• Rhodium Fluorapatite Catalyst for the Synthesis of Trisubstituted Olefins via Cross Coupling of Baylis−Hillman Adducts and Arylboronic Acids
  作者：M. Lakshmi Kantam、K. B. Shiva Kumar、B. Sreedhar

  DOI：10.1021/jo701982m

  日期：2008.1.1

  [GRAPHICS]For R-2 = CN, Z-isomer (99%) was obtained.Treatment of fluorapatite (prepared by incorporating basic species F- in apatite in situ by coprecipitation) with an aqueous solution of RhCl3 resulted in rhodium-exchanged fluorapatite catalyst (RhFAP), which successfully promoted cross coupling of Baylis-Hillman adducts with arylboronic acids to yield trisubstituted olefins. A variety of arylboronic acids and Baylis-Hillman adducts were converted to the corresponding trisubstituted olefins, demonstrating the versatility of the reaction. The reaction is highly stereoselective. RhFAP was recovered quantitatively by simple filtration and reused with almost consistent activity.