methyl (4E)-5-(3-methoxyphenyl)-2-diazo-3-oxopent-4-enoate | 1446109-55-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl (4E)-5-(3-methoxyphenyl)-2-diazo-3-oxopent-4-enoate
• CAS: 1446109-55-2
• 化学式: C₁₃H₁₂N₂O₄
• 分子量: 260.249
• InChiKey: BOOIKSUEFPBVLH-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  89.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (4E)-5-(3-methoxyphenyl)-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93%的产率得到dimethyl 5-(3-methoxyphenyl)-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-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68%的产率得到methyl (4E)-5-(3-methoxyphenyl)-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

文献信息

• Sc(OTf)3-Catalyzed [3+2]-Cycloaddition of Diazoacetoacetate Enones and N-Aryl Nitrones: Diastereoselective Synthesis of Functionalized Isoxazolidines with Three Contiguous Stereogenic Centers
  作者：Xichen Xu、Yingjun Zhao、Di Wu

  DOI：10.1055/s-0041-1737804

  日期：2022.5

  A catalytic [3+2]-cycloaddition using Sc(OTf)3 as a Lewis acid catalyst is developed. This catalytic 1,3-dipolar cycloaddition dia­stereoselectively transforms diazoacetoacetate enones and N-aryl nitrones into highly functionalized isoxazolidines bearing three contiguous chiral centers. The feasibility of the uncatalyzed 1,3-dipolar cycloaddition is postulated by DFT calculations and substantiated

  开发了使用Sc(OTf) 3作为路易斯酸催化剂的催化[3+2]-环加成反应。这种催化的 1,3-偶极环加成非对映选择性将重氮乙酰乙酸烯酮和N-芳基硝酮转化为具有三个连续手性中心的高度官能化的异恶唑烷。未催化的 1,3-偶极环加成的可行性由 DFT 计算假设并通过实验证实。