dimethyl 2-[(E)-styryl]maleate | 106352-52-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl 2-[(E)-styryl]maleate
• 英文别名: (2Z,4E)-2-styrylbut-2-enedioic acid dimethyl ester；dimethyl (Z)-2-[(E)-2-phenylethenyl]but-2-enedioate
• CAS: 106352-52-7
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: XWBTXBQLFSSBFV-ZLNDROGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  [(E)-2-苯基乙烯基]硼酸 、 丁炔二酸二甲酯 在 dicarbonylacetylacetonato rhodium (I) 作用下， 以 水 、 甲苯 为溶剂， 以77%的产率得到dimethyl 2-[(E)-styryl]maleate
  参考文献：
  名称：

  A Homogeneous, Recyclable Polymer Support for Rh(I)-Catalyzed C–C Bond Formation

  摘要：

  A robust and practical polymer-supported, homogeneous, recyclable biphephos rhodium(I) catalyst has been developed for C-C bond formation reactions. Control of polymer molecular weight allowed tuning of the polymer solubility such that the polymer-supported catalyst is soluble in nonpolar solvents and insoluble in polar solvents. Using the supported rhodium catalysts, addition of aryl and vinylboronic acids to the electrophiles such as enones, aldehydes, N-sulfonyl aldimines, and alkynes occurs smoothly to provide products in high yields. Additions of terminal alkynes to enones and industrially relevant hydroformylation reactions have also been successfully carried out. Studies show that the leaching of Rh from the polymer support is low and catalyst recycle can be achieved by simple precipitation and filtration.

  DOI：

  10.1021/jo201476h

文献信息

• Rhodium-Catalyzed Regio- and Stereoselective Codimerization of Alkenes and Electron-Deficient Internal Alkynes Leading to 1,3-Dienes
  作者：Yu Shibata、Masao Hirano、Ken Tanaka

  DOI：10.1021/ol800995r

  日期：2008.7.3

  A cationic rhodium(I)/H(8)-BINAP complex catalyzes codimerization of alkenes bearing no alpha-hydrogen and electron-deficient internal alkynes, leading to 1,3-dienes in good yields with moderate to excellent regio- and stereoselectivity. The same complex also catalyzes codimerization of an acrylate and phenyl-substituted electron-rich internal alkynes, leading to 1,3-dienes.

  阳离子铑（I）/ H（8）-BINAP络合物催化不带α-氢和电子不足的内部炔烃的烯烃共二聚，从而以高收率产生1,3-二烯，具有中等至出色的区域选择性和立体选择性。相同的配合物还催化丙烯酸酯和苯基取代的富含电子的内部炔烃的共二聚反应，生成1,3-二烯。
• Decarboxylative olefination of potassium benzoates via bimetallic catalysis strategy
  作者：Mehdi Khalaj、Majid Ghazanfarpour-Darjani、Saeed Taheri、Sajjad Sedaghat、Seyed Jalal Hoseyni

  DOI：10.1007/s00706-018-2267-y

  日期：2018.11

  A novel synthesis of styrene derivatives through decaroxylative olefination of potassium benzoates with alkynes using Pd(2)dba(3)/CuBr as catalyst system has been developed. The protocol proceeded smoothly and in most cases Z-alkene was the main product. Electron-rich potassium benzoates reacted more efficiently than those of electron-deficient substrates. Heteroaromatic and electron-deficient aryl alkynes were not consistent with this transformation.[GRAPHICS].