1,4-Dicarbomethoxy-3-cyano-1,2-dihydro-2-quinolinone

• 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: 1,4-Dicarbomethoxy-3-cyano-1,2-dihydro-2-quinolinone
• 英文别名: Dimethyl 3-cyano-2-oxoquinoline-1,4-dicarboxylate
• 化学式: C₁₄H₁₀N₂O₅
• 分子量: 286.244
• InChiKey: AAEPOTYPUKKZLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  96.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  Methyl (Z)-3-(1-cyano-2-methoxy-2-oxoethylidene)-2,3-dihydro-2-oxo-1H-indole-1-carboxylate 以 甲醇 为溶剂， 反应 3.0h， 以81%的产率得到1,4-Dicarbomethoxy-3-cyano-1,2-dihydro-2-quinolinone
  参考文献：
  名称：

  Mechanistic Studies of the Ring Expansion Reaction of Isatylidenes to Quinolines

  摘要：

  DOI：

  10.1021/jo00124a041

文献信息

• Microwave-Assisted Synthesis of 3,1-Benzoxazin-2-ones from 3-Hydroxyoxindoles
  作者：Oscar R. Suárez-Castillo、Claudia I. Bautista-Hernández、Maricruz Sánchez-Zavala、Myriam Meléndez-Rodríguez、Araceli Sierra-Zenteno、Martha S. Morales-Ríos、Pedro Joseph-Nathan

  DOI：10.3987/com-12-12472

  日期：——

  A general protocol for the synthesis of 3,1-benzoxazin-2-ones 18 from 3-hydroxyoxindoles 16 in a two steps sequence through phenylsuccinates or phenylpropionates 17 is described. Best reaction conditions for ring opening of 16 to succinates or propionates 17 were achieved using alcohol/silica gel, while cyclization of 17 to benzoxazinones 18 was easily done with HCl/alcohol. It was also found that 17 and 18 can be transesterified using HCl/alcohol. Most transformations were carried out by traditional heating and by microwave (MW) irradiation to accelerate reaction rates.
• Mechanistic Studies of the Ring Expansion Reaction of Isatylidenes to Quinolines
  作者：Martha S. Morales-Rios、Nelda X. Martinez-Galero、Manuel Loeza-Coria、Pedro Joseph-Nathan

  DOI：10.1021/jo00124a041

  日期：1995.9