methyl (4E)-5-(3,4-dimethoxyphenyl)-2-diazo-3-oxopent-4-enoate | 1446109-54-1

• 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 (4E)-5-(3,4-dimethoxyphenyl)-2-diazo-3-oxopent-4-enoate
• CAS: 1446109-54-1
• 化学式: C₁₄H₁₄N₂O₅
• 分子量: 290.276
• InChiKey: GZJNMXOFMWSTMC-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  98.23
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (4E)-5-(3,4-dimethoxyphenyl)-2-diazo-3-oxopent-4-enoate 、 1-(叔丁基二甲基硅氧基)-1-甲氧基乙烯 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以94%的产率得到dimethyl 5-(3,4-dimethoxyphenyl)-2-diazo-3-oxoheptane-1,7-dioate
  参考文献：
  名称：

  Diazoacetoacetate Enones for the Synthesis of Diverse Natural Product-like Scaffolds

  摘要：

  Diazoacetoacetate enones are a new class of Michael acceptors that enable the efficient construction of natural product-like scaffolds. Through their Michael addition reactions, including those with silyl enol ethers, indoles, pyrroles, and amines, delta-functionalized diazoacetoacetates are formed in high yield and with overall operational efficiency. Subsequent catalytic dinitrogen extrusion reactions provide access to a diverse series of natural product-like carbo- and heterocyclic ring systems in only three steps from commercial materials.

  DOI：

  10.1021/ol4015199
• 作为产物：
  描述：

  methyl 3-oxo-4-(triphenylphosphoranylidene)butanoate 、 3,4-二甲氧基苯甲醛 在 三乙烯二胺 、 sodium hydride 、 4-乙酰氨基苯磺酰叠氮 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 以69%的产率得到methyl (4E)-5-(3,4-dimethoxyphenyl)-2-diazo-3-oxopent-4-enoate
  参考文献：
  名称：

  Diazoacetoacetate Enones for the Synthesis of Diverse Natural Product-like Scaffolds

  摘要：

  Diazoacetoacetate enones are a new class of Michael acceptors that enable the efficient construction of natural product-like scaffolds. Through their Michael addition reactions, including those with silyl enol ethers, indoles, pyrroles, and amines, delta-functionalized diazoacetoacetates are formed in high yield and with overall operational efficiency. Subsequent catalytic dinitrogen extrusion reactions provide access to a diverse series of natural product-like carbo- and heterocyclic ring systems in only three steps from commercial materials.

  DOI：

  10.1021/ol4015199