1-(2-chloro-6-methylquinolin-3-yl)ethanone

• 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-(2-chloro-6-methylquinolin-3-yl)ethanone
• 英文别名: 3-acetyl-2-chloro-6-methylquinoline
• 化学式: C₁₂H₁₀ClNO
• 分子量: 219.671
• InChiKey: HLKLWBSKRYAKOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,2-三氟-N-苯基亚氨代乙酰氯 、 1-(2-chloro-6-methylquinolin-3-yl)ethanone 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以45%的产率得到7-methyl-1-phenyl-2-(trifluoromethyl)benzo[b][1,8]naphthyridin-4(1H)-one
  参考文献：
  名称：

  Synthesis of 2-(trifluoromethyl)benzo[b][1,8]naphthyridin-4(1H)-one derivatives using trifluoroacetimidoyl chlorides

  摘要：

  A simple protocol is described for the synthesis of 2-(trifluoromethyl)benzo[b][1,8]naphthyridin-4(1 H)one derivatives. The reaction between diverse 2-chloro-3-acetyl-quinolines with trifluoroacetimidoyl chlorides using sodium hydride in THF at room temperature gives directly the title compounds without isolation of intermediates. Starting 2-chloro-3-acetyl-quinolines were easily prepared in two steps from readily available 2-chloro-3-formyl-quinolines. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.10.014
• 作为产物：
  描述：

  2-氯-6-甲基喹啉-3-甲醛 在 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-(2-chloro-6-methylquinolin-3-yl)ethanone
  参考文献：
  名称：

  Synthesis of 2-(trifluoromethyl)benzo[b][1,8]naphthyridin-4(1H)-one derivatives using trifluoroacetimidoyl chlorides

  摘要：

  A simple protocol is described for the synthesis of 2-(trifluoromethyl)benzo[b][1,8]naphthyridin-4(1 H)one derivatives. The reaction between diverse 2-chloro-3-acetyl-quinolines with trifluoroacetimidoyl chlorides using sodium hydride in THF at room temperature gives directly the title compounds without isolation of intermediates. Starting 2-chloro-3-acetyl-quinolines were easily prepared in two steps from readily available 2-chloro-3-formyl-quinolines. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.10.014

文献信息

• Symmetrical Trichlorotriazine Derivatives as Efficient Reagents for One-Pot Synthesis of 3-Acetyl-2-chloroquinolines from Acetanilides under Vilsmeier–Haack Conditions
  作者：K. Rajanna、Bhooshan Muddam、P. Venkanna、M. Venkateswarlu、M. Satish Kumar

  DOI：10.1055/s-0036-1589099

  日期：2018.1

  Symmetrical trichlorotriazine derivatives such as 2,4,6-trichloro-1,3,5-triazine and trichloroisocyanuric acid were explored as Vilsmeier–Haack type reagents in the presence of N,N-dimethylacetamide for the effective synthesis of 3-acetyl-2-chloroquinolines from acetanilides. Ultrasonication led to shorter reaction times than conventional heating and gave yields comparable to those obtained under reflux conditions.

  对称三氯三嗪衍生物，如2,4,6-三氯-1,3,5-三嗪和三氯异氰尿酸，被探索用作Vilsmeier-Haack型试剂，在N,N-二甲基乙酰胺存在下，有效合成了3-乙酰基-2-氯喹啉，从乙酰苯胺中。超声波处理比传统加热导致更短的反应时间，并且产率与在回流条件下获得的产率相媲美。
• Synthesis of 2-(trifluoromethyl)benzo[b][1,8]naphthyridin-4(1H)-one derivatives using trifluoroacetimidoyl chlorides
  作者：Angel H. Romero、José Salazar、Simón E. López

  DOI：10.1016/j.jfluchem.2014.10.014

  日期：2015.1

  A simple protocol is described for the synthesis of 2-(trifluoromethyl)benzo[b][1,8]naphthyridin-4(1 H)one derivatives. The reaction between diverse 2-chloro-3-acetyl-quinolines with trifluoroacetimidoyl chlorides using sodium hydride in THF at room temperature gives directly the title compounds without isolation of intermediates. Starting 2-chloro-3-acetyl-quinolines were easily prepared in two steps from readily available 2-chloro-3-formyl-quinolines. (C) 2014 Elsevier B.V. All rights reserved.