3-[(2-chloro-6-methylquinolin-3-yl)methyl]pyrimidine-4(3H)-one | 1227302-50-2

• 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: 3-[(2-chloro-6-methylquinolin-3-yl)methyl]pyrimidine-4(3H)-one
• 英文别名: 3-[(2-Chloro-6-methylquinolin-3-yl)methyl]pyrimidin-4-one
• CAS: 1227302-50-2
• 化学式: C₁₅H₁₂ClN₃O
• 分子量: 285.733
• InChiKey: HHPMOJFHVNYVFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4(3H)-嘧啶酮 、 2-氯-3-(氯甲基)-6-甲基喹啉 在 铁粉 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以88%的产率得到3-[(2-chloro-6-methylquinolin-3-yl)methyl]pyrimidine-4(3H)-one
  参考文献：
  名称：

  Fe nano particles mediated C–N bond-forming reaction: Regioselective synthesis of 3-[(2-chloroquinolin-3-yl)methyl]pyrimidin-4(3H)ones

  摘要：

  An efficient and regioselective N-alkylation of 4(3H)-pyrimidone with various electrophiles in the presence of Fe nano particle is reported. The catalyst initiates N-alkylation of amides by alkyl chlorides. The reaction of equimolar 4(3H)-pyrimidone and 2-chloro-3-(chloromethyl)quinolines in the presence of KOH and Fe nano particle (5 mol %) m DMSO solution under reflux condition formed 3-[(2-chloroquinolin-3-yl]methyppyrimiclin-4(3H)ones. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.128

文献信息

• Regioselective N-alkylation of (2-chloroquinolin-3-yl) methanol with N-heterocyclic compounds using the Mitsunobu reagent
  作者：Selvaraj Roopan、Fazlur-Rahman Khan、Jong Jin

  DOI：10.2478/s11696-011-0018-1

  日期：2011.1.1

  The Mitsunobu reaction is a well-established fundamental reaction and has been widely applied in organic synthesis. In this paper, under Mitsunobu conditions dehydration proceeds between (2-chloroquinolin-3-yl)methanol and nitrogen heterocyclic compounds such as quinazolinone, pyrimidone, 2-oxoquinoline in dry THF in the presence of triethylamine, triphenylphosphane and diethyl azodicarboxylate to give the corresponding products. As part of our recent research, we attempted to couple two N-heterocyclic compounds under Mitsunobu reaction conditions to provide efficient building blocks for natural product synthesis.

  三宅信夫反应是一种被广泛应用于有机合成中的基础反应。本文中，在三宅信夫条件下，(2-氯喹啉-3-基)甲醇与喹唑啉酮、嘧啶酮、2-氧喹啉等氮杂环化合物在干燥的THF中，在三乙胺、三苯基膦和双乙基偶氮二甲酸酯的存在下发生脱水反应，生成相应的产物。作为我们最近研究的一部分，我们尝试在三宅信夫反应条件下耦合两种N-杂环化合物，以提供天然产物合成的高效构建块。