ethyl (2E)-3-{2-[(3-ethoxy-3-oxopropoxy)methyl]-4,5-dimethoxyphenyl}acrylate | 1401416-08-7

• 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: ethyl (2E)-3-{2-[(3-ethoxy-3-oxopropoxy)methyl]-4,5-dimethoxyphenyl}acrylate
• 英文别名: ethyl 3-[[2-[(E)-3-ethoxy-3-oxoprop-1-enyl]-4,5-dimethoxyphenyl]methoxy]propanoate
• CAS: 1401416-08-7
• 化学式: C₁₉H₂₆O₇
• 分子量: 366.411
• InChiKey: PFZKNGPXSPRIIA-BQYQJAHWSA-N

物化性质

• 沸点：
  495.9±40.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl (2E)-3-{2-[(3-ethoxy-3-oxopropoxy)methyl]-4,5-dimethoxyphenyl}acrylate 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 36.0h， 生成 7,8-dimethoxy-2-benzoxepin-3(1H)-one
  参考文献：
  名称：

  Sequential one-pot method for oxy-Michael addition, Heck coupling, and degradation followed by condensation: facile synthesis of 2-benzoxepin-3(1H)-ones

  摘要：

  A sequential one-pot intermolecular oxy-Michael addition, intermolecular Heck coupling, and intramolecular degradation (retro-oxy-Michael addition) followed by condensation method has been developed for the synthesis of interesting 2-benzoxepin-3(1H)-ones. Significantly, the 2-benzoxepin-3(1H)-ones form the core quantum of biologically vital natural products. The initial oxy-Michael addition and Heck coupling steps involve a straight forward construction of C-O and C-C bonds, whereas, the final condensation step follows a novel mechanistic path via intramolecular degradation, double bond isomerization, and intramolecular condensation. Notably, a remarkable solvent effect has been observed in-order to promote the final intramolecular condensation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.050
• 作为产物：
  描述：

  6-溴藜芦醛 在 sodium tetrahydroborate 、 caesium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.0h， 生成 ethyl (2E)-3-{2-[(3-ethoxy-3-oxopropoxy)methyl]-4,5-dimethoxyphenyl}acrylate
  参考文献：
  名称：

  有效的顺序一锅碱基介导的C–O和Pd介导的C–C键形成：官能化肉桂酸酯和异色酮的合成

  摘要：

  提出了一种有效的顺序单锅分子间氧-迈克尔加成反应和分子间Heck偶联反应，用于功能化肉桂酸酯的合成。粗大的丙烯酸叔丁酯被认为是更适合的初始氧-迈克尔加成反应的迈克尔受体，因为它阻止了不希望的交叉缩合酯的形成。最重要的是，本发明的方法进一步扩展到通过顺序一锅法O-烯丙基化和随后的分子内Heck环化成功合成异色酮。

  DOI：

  10.1016/j.tetlet.2012.08.023

文献信息

• An efficient sequential one-pot base mediated C–O and Pd-mediated C–C bond formation: synthesis of functionalized cinnamates and isochromenes
  作者：A. Gopi Krishna Reddy、J. Krishna、G. Satyanarayana

  DOI：10.1016/j.tetlet.2012.08.023

  日期：2012.10

  An efficient sequential one-pot intermolecular oxy-Michael addition and intermolecular Heck coupling for the synthesis of functionalized cinnamates is presented. Bulky tert-butyl acrylate was identified as a more suitable Michael acceptor for initial oxy-Michael addition, as it precludes the formation of undesired cross condensed ester. Most importantly, the present method was further divergently extended

  提出了一种有效的顺序单锅分子间氧-迈克尔加成反应和分子间Heck偶联反应，用于功能化肉桂酸酯的合成。粗大的丙烯酸叔丁酯被认为是更适合的初始氧-迈克尔加成反应的迈克尔受体，因为它阻止了不希望的交叉缩合酯的形成。最重要的是，本发明的方法进一步扩展到通过顺序一锅法O-烯丙基化和随后的分子内Heck环化成功合成异色酮。
• Sequential one-pot method for oxy-Michael addition, Heck coupling, and degradation followed by condensation: facile synthesis of 2-benzoxepin-3(1H)-ones
  作者：A. Gopi Krishna Reddy、J. Krishna、G. Satyanarayana

  DOI：10.1016/j.tet.2013.09.050

  日期：2013.11

  A sequential one-pot intermolecular oxy-Michael addition, intermolecular Heck coupling, and intramolecular degradation (retro-oxy-Michael addition) followed by condensation method has been developed for the synthesis of interesting 2-benzoxepin-3(1H)-ones. Significantly, the 2-benzoxepin-3(1H)-ones form the core quantum of biologically vital natural products. The initial oxy-Michael addition and Heck coupling steps involve a straight forward construction of C-O and C-C bonds, whereas, the final condensation step follows a novel mechanistic path via intramolecular degradation, double bond isomerization, and intramolecular condensation. Notably, a remarkable solvent effect has been observed in-order to promote the final intramolecular condensation. (C) 2013 Elsevier Ltd. All rights reserved.