ethyl (Z)-2,3-bis(4-methoxyphenyl)but-2-enoate

• 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 (Z)-2,3-bis(4-methoxyphenyl)but-2-enoate
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: LTDQWAJISFUELW-RGEXLXHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl (Z)-3-chloro-2-(4-methoxyphenyl)but-2-enoate 、 4-甲氧基苯硼酸 在 palladium diacetate 三甲基磷四氟硼酸酯 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 以95%的产率得到ethyl (Z)-2,3-bis(4-methoxyphenyl)but-2-enoate
  参考文献：
  名称：

  A simple method to prepare single isomer tetrasubstituted olefins by successive Suzuki–Miyaura cross-couplings of E-β-chloro-α-iodo-α,β-unsaturated esters

  摘要：

  A convenient method of synthesizing tetrasubstituted olefins as single isomers is described. E-beta-Chloro-alpha-iodo-alpha,beta-unsaturatecl esters are first converted into the corresponding E-beta-chloro-alpha,beta-unsaturatedesters using Suzuki-Miyaura coupling reactions with arylboronic acids and alkenylboronic acids. These transformations gave complete selectivity, and proceeded with substitution at the more activated alpha-iodide position. These compounds, isolated as single isomers, were then transformed into tetrasubstituted olefins by Suzuki-Miyaura couplings with arylboronic acids, alkenylboronic acids, and alkyl boranes to afford the corresponding tetrasubstituted olefins as single isomers. During this coupling process, it was discovered that the use of small ligands, such as PMe3 or PEt3, was critical for efficient coupling. The stereochemistry and regiochemistry of the products were unequivocally established using NMR methods. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.004

文献信息

• Palladium-mediated cross-coupling reactions involving 3-substituted alkyl (E)-2,3-dibromopropenoates and arylzinc or aryltin derivatives
  作者：Renzo Rossi、Fabio Bellina、Adriano Carpita、Felice Mazzarella

  DOI：10.1016/s0040-4020(96)00071-3

  日期：1996.3

  Stereodefined unsymmetrically 3,3-disubstituted alkyl 2-bromopropenoates, 5, were regioselectively prepared by Pd-mediated reactions between 3-alkyl, 3-aryl and 3-alkoxycarbonyl substituted (E)-2,3-dibromopropenoates, (E)-7, and aryl or 1-alkynylzinc chlorides. The stereospecificity of these reactions was found to be dependent on the type of substituent present in the 3-position of (E)-7. The (E)-stereochemistry of compounds 5b, 5d and 5i so prepared was confirmed by their conversion into the corresponding 4-substituted 3-bromocoumarins. Tetrasubstituted alpha,beta-unsaturated esters 10 were then synthesized by Pd-mediated reactions either of (E)-7 with a molar excess of an arylzinc chloride or an aryltributylstannane, or of a compound of general formula 5 with an aryltributylstannane. An examination of the parameters which influence the stereochemistry and the yields of these arylations was made.
• A simple method to prepare single isomer tetrasubstituted olefins by successive Suzuki–Miyaura cross-couplings of E-β-chloro-α-iodo-α,β-unsaturated esters
  作者：Julie Simard-Mercier、Alison B. Flynn、William W. Ogilvie

  DOI：10.1016/j.tet.2008.04.004

  日期：2008.6

  A convenient method of synthesizing tetrasubstituted olefins as single isomers is described. E-beta-Chloro-alpha-iodo-alpha,beta-unsaturatecl esters are first converted into the corresponding E-beta-chloro-alpha,beta-unsaturatedesters using Suzuki-Miyaura coupling reactions with arylboronic acids and alkenylboronic acids. These transformations gave complete selectivity, and proceeded with substitution at the more activated alpha-iodide position. These compounds, isolated as single isomers, were then transformed into tetrasubstituted olefins by Suzuki-Miyaura couplings with arylboronic acids, alkenylboronic acids, and alkyl boranes to afford the corresponding tetrasubstituted olefins as single isomers. During this coupling process, it was discovered that the use of small ligands, such as PMe3 or PEt3, was critical for efficient coupling. The stereochemistry and regiochemistry of the products were unequivocally established using NMR methods. (C) 2008 Elsevier Ltd. All rights reserved.