(E)-2-(4-methoxybenzyl)-3-phenylacrylic acid methyl ester | 596813-87-5

• 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-methoxybenzyl)-3-phenylacrylic acid methyl ester
• 英文别名: 2-(4'-methoxybenzyl)-3-phenylacrylic acid methyl ester；methyl (E)-2-(4-methoxybenzyl)-3-phenylprop-2-enoate
• CAS: 596813-87-5
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: CGDDHXMUCCTDDM-FOWTUZBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.49
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  methyl 2-{[(tert-butoxycarbonyl)oxy](phenyl)methyl}acrylate 、 5-(4-methoxyphenyl)-5H-thianthren-5-ium trifluoromethanesulfonate 在 Eosin Y 、 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 以63 %的产率得到(E)-2-(4-methoxybenzyl)-3-phenylacrylic acid methyl ester
  参考文献：
  名称：

  Thianthrenation-promoted photoinduced alkene difunctionalization and aryl allylation with Morita–Baylis–Hillman adducts

  摘要：

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

  DOI：

  10.1039/d4cc01792g

文献信息

• Rhodium-Catalyzed Formation of Stereocontrolled Trisubstituted Alkenes from Baylis-Hillman Adducts
  作者：Thomas Gendrineau、Nicolas Demoulin、Laure Navarre、Jean-Pierre Genet、Sylvain Darses

  DOI：10.1002/chem.200802276

  日期：2009.4.27

  Efficient and general conditions for the formation of stereodefined trisubstituted alkenes by using the rhodium‐catalyzed reaction of unactivated Baylis–Hillman adducts with either organoboronic acids or potassium trifluoro(organo)borates are reported (see scheme).

  据报道，通过铑催化未活化的Baylis-Hillman加合物与有机硼酸或三氟（有机）硼酸钾的反应，可形成立体定义的三取代烯烃的高效通用条件（参见方案）。
• 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.
• Palladium-Catalyzed Cross-Coupling of Acetates of Baylis−Hillman Adducts and Potassium Organotrifluoroborates
  作者：George W. Kabalka、Bollu Venkataiah、Gang Dong

  DOI：10.1021/ol0351798

  日期：2003.10.1

  [GRAPHICS]The cross-coupling of potassium organotrifluoroborates and acetates of Baylis-Hillman adducts proceeds readily in moderate to excellent yield in the presence of Pd(OAc)(2). The reaction tolerates hindered trifluoroborate salts, and the process is stereoselective.