methyl 3-<2'-(2-carbomethoxyethyl)-4',5'-dimethoxyphenyl>-2-propenoate | 139527-74-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl 3-<2'-(2-carbomethoxyethyl)-4',5'-dimethoxyphenyl>-2-propenoate
• 英文别名: methyl 3-[4,5-dimethoxy-2-[(E)-3-methoxy-3-oxoprop-1-enyl]phenyl]propanoate
• CAS: 139527-74-5
• 化学式: C₁₆H₂₀O₆
• 分子量: 308.331
• InChiKey: GGTNVNZZKSZDRN-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-<2'-(2-carbomethoxyethyl)-4',5'-dimethoxyphenyl>-2-propenoate 在 methanolate 、 deuteriomethanol 作用下， 生成
  参考文献：
  名称：

  An unusual doubly substituted product from the phase-transfer-catalyzed Heck reactions of o-bromobenzaldehydes with methyl acrylate

  摘要：

  The reactions of o-bromobenzaldehydes with methyl acrylate under Heck conditions and with phase-transfer catalysis to yield significant amounts of doubly substituted deformylated products 1A-E in addition to the expected o-formyl cinnamates 2A-E are reported. X-ray crystallography of one such product (4) established that the bromine was replaced by a propionate and the formyl group by an acrylate residue. Employment of deuterium-labeled substrates showed that the hydrogen atom of the formyl group of the substrate was transferred intramolecularly and regiospecifically to the benzylic carbon of the propionate substituent of the product. A tentative hypothesis is advanced to explain these and other experimental findings.

  DOI：

  10.1021/jo00034a041
• 作为产物：
  描述：

  6-溴藜芦醛 、 丙烯酸甲酯（MA） 生成 (E)-3-(2-Dimethoxymethyl-4,5-dimethoxy-phenyl)-acrylic acid methyl ester 、 methyl 3-<2'-(2-carbomethoxyethyl)-4',5'-dimethoxyphenyl>-2-propenoate
  参考文献：
  名称：

  An unusual doubly substituted product from the phase-transfer-catalyzed Heck reactions of o-bromobenzaldehydes with methyl acrylate

  摘要：

  The reactions of o-bromobenzaldehydes with methyl acrylate under Heck conditions and with phase-transfer catalysis to yield significant amounts of doubly substituted deformylated products 1A-E in addition to the expected o-formyl cinnamates 2A-E are reported. X-ray crystallography of one such product (4) established that the bromine was replaced by a propionate and the formyl group by an acrylate residue. Employment of deuterium-labeled substrates showed that the hydrogen atom of the formyl group of the substrate was transferred intramolecularly and regiospecifically to the benzylic carbon of the propionate substituent of the product. A tentative hypothesis is advanced to explain these and other experimental findings.

  DOI：

  10.1021/jo00034a041