ethyl 10-chloro-4-methyl-7-oxo-6-phenyl-1,2,6,7-tetrahydrobenzo[b]imidazo[1,2,3-ij] [1,8]naphthyridine-5-carboxylate | 1256150-87-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 10-chloro-4-methyl-7-oxo-6-phenyl-1,2,6,7-tetrahydrobenzo[b]imidazo[1,2,3-ij] [1,8]naphthyridine-5-carboxylate
• 英文别名: Ethyl 4-chloro-12-methyl-8-oxo-10-phenyl-1,13-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-2(7),3,5,9(16),11-pentaene-11-carboxylate
• CAS: 1256150-87-4
• 化学式: C₂₄H₂₁ClN₂O₃
• 分子量: 420.895
• InChiKey: LACOURIDOWOXEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 8-(2,4-dichlorobenzoyl)-5-methyl-7-phenyl-1,2,3,7-tetrahydroimidazo[1,2-a]pyridine-6-carboxylate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以100%的产率得到ethyl 10-chloro-4-methyl-7-oxo-6-phenyl-1,2,6,7-tetrahydrobenzo[b]imidazo[1,2,3-ij] [1,8]naphthyridine-5-carboxylate
  参考文献：
  名称：

  Modulating the Reactivity of Heterocyclic Ketene Aminals in MCR: Selective Construction of Tetrahydrobenzo[b]imidazo[3,2,1-ij][1,8]naphthyridines

  摘要：

  Two new kinds of tetrahydrobenzo[b]imidazo[3,2,1-iota j][1,8]naphthyndine derivatives have been successfully synthesized by cascade reactions including Knoevenagel condensation, aza-ene reaction, imine-enamine tautomenzation, cyclocondensation, and intramolecular SNAr of precursors 2-(2-chloroaroyl)methyleneimidazolidines with aromatic aldehydes and ethyl acetoacetate or Meldrum's acid under mild conditions, respectively These studies highlighted the concept of a substrate-design approach to the development of novel multicomponent reactions by simply incorporating an o-halo group into the aryl ring of 2-benzoyl-methyleneimidazolidine as new synthons In this domino reaction, at least six different active sites are involved, two C-C bonds, two C-N bonds, and two new rings are constructed with all reactants efficiently utilized in the chemical transformation

  DOI：

  10.1021/jo101454q

文献信息

• Modulating the Reactivity of Heterocyclic Ketene Aminals in MCR: Selective Construction of Tetrahydrobenzo[<i>b</i>]imidazo[3,2,1-<i>ij</i>][1,8]naphthyridines
  作者：Li-Rong Wen、Chao Liu、Ming Li、Li-Juan Wang

  DOI：10.1021/jo101454q

  日期：2010.11.19

  Two new kinds of tetrahydrobenzo[b]imidazo[3,2,1-iota j][1,8]naphthyndine derivatives have been successfully synthesized by cascade reactions including Knoevenagel condensation, aza-ene reaction, imine-enamine tautomenzation, cyclocondensation, and intramolecular SNAr of precursors 2-(2-chloroaroyl)methyleneimidazolidines with aromatic aldehydes and ethyl acetoacetate or Meldrum's acid under mild conditions, respectively These studies highlighted the concept of a substrate-design approach to the development of novel multicomponent reactions by simply incorporating an o-halo group into the aryl ring of 2-benzoyl-methyleneimidazolidine as new synthons In this domino reaction, at least six different active sites are involved, two C-C bonds, two C-N bonds, and two new rings are constructed with all reactants efficiently utilized in the chemical transformation