ethyl 6-chloro-2-(chloromethyl)quinoline-3-carboxylate | 1431472-20-6

• 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 6-chloro-2-(chloromethyl)quinoline-3-carboxylate
• CAS: 1431472-20-6
• 化学式: C₁₃H₁₁Cl₂NO₂
• 分子量: 284.142
• InChiKey: VPVGJYXJQVLMDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 6-chloro-2-(chloromethyl)quinoline-3-carboxylate 在 氨 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以68%的产率得到7-chloro-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one
  参考文献：
  名称：

  A General Synthesis of Novel Quinoline-Based Isoindolin-1-one Derivatives

  摘要：

  A simple and general one-pot protocol for the synthesis of a series quinoline-based isoindolin-l-ones, namely 7-chloro-2-substituted-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-l-ones (5a-p) is described, involving a cascade Williamson-type condensation reaction of ethyl 6-chloro-2-(chloromethyl)quinoline-3-carboxylate (3) with aromatic amines (4 a-i), aliphatic amines (4j-m) and aliphatic diamines (4n-p) and subsequent intramolecular C-N bond cyclization of the resulting intermediates in refluxing EtOH-AcOH (v/v, 10:1) solvent system in a single synthetic operation.

  DOI：

  10.3987/com-15-13314
• 作为产物：
  描述：

  N-(2-甲酰基苯基)乙酰胺 在 N-氯代丁二酰亚胺 、 三甲基氯硅烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 ethyl 6-chloro-2-(chloromethyl)quinoline-3-carboxylate
  参考文献：
  名称：

  A General Synthesis of Novel Quinoline-Based Isoindolin-1-one Derivatives

  摘要：

  A simple and general one-pot protocol for the synthesis of a series quinoline-based isoindolin-l-ones, namely 7-chloro-2-substituted-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-l-ones (5a-p) is described, involving a cascade Williamson-type condensation reaction of ethyl 6-chloro-2-(chloromethyl)quinoline-3-carboxylate (3) with aromatic amines (4 a-i), aliphatic amines (4j-m) and aliphatic diamines (4n-p) and subsequent intramolecular C-N bond cyclization of the resulting intermediates in refluxing EtOH-AcOH (v/v, 10:1) solvent system in a single synthetic operation.

  DOI：

  10.3987/com-15-13314

文献信息

• Lithium triflate (LiOTf): a highly efficient and reusable catalytic system for the synthesis of diversified quinolines under neat conditions
  作者：Amol B. Atar、Someshwer D. Dindulkar、Yeon Tae Jeong

  DOI：10.1007/s00706-012-0906-2

  日期：2013.5

  A series of diverse polyfunctionalized quinolines were easily prepared in excellent yields via a Friedlander reaction of o-aminoaryl ketone or o-aminoaryl aldehyde with alpha-methylene ketones using lithium triflate as an expeditious catalyst under solvent free conditions. The protocol provides a practical and straightforward approach toward highly functionalized quinoline derivatives in excellent yields. The catalyst is easily recoverable and less sensitive to moisture, which makes this protocol more advantageous.