6-methyl-4-n-butyl-2-phenylquinoline

• 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: 6-methyl-4-n-butyl-2-phenylquinoline
• 英文别名: 4-butyl-6-methyl-2-phenylquinoline；6-methyl-4-butyl-2-phenylquinoline
• 化学式: C₂₀H₂₁N
• 分子量: 275.393
• InChiKey: SJBYFBPFWSKCJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-苯基-庚-2-炔-1-酮 、 3-碘-4-甲基苯胺 在 dibromo[1,2-bis(diphenylphosphino)ethane]nickel(II) 锌 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以76%的产率得到6-methyl-4-n-butyl-2-phenylquinoline
  参考文献：
  名称：

  Nickel-Catalyzed Cyclization of 2-Iodoanilines with Aroylalkynes:  An Efficient Route for Quinoline Derivatives

  摘要：

  An efficient and convenient nickel-catalyzed cyclization of 2-iodoanilines with alkynyl aryl ketones to give 2,4-disubstituted quinolines was developed. The reaction can be employed for the synthesis of naturally occurring quinoline derivatives in good yields. On the basis of the regiochemistry of the products, the possible pathway for the reaction is via the formation of o-aminochalcone.

  DOI：

  10.1021/jo060800d

文献信息

• Triple zirconocene/brønsted acid/CuO cooperative and relay catalysis system for tandem Mannich addition/C–C formative cyclization/oxidation
  作者：Yanlong Luo、Huaming Sun、Weiqiang Zhang、Xiu Wang、Shan Xu、Guofang Zhang、Yajun Jian、Ziwei Gao

  DOI：10.1039/c7ra00870h

  日期：——

  A new triple cooperative and relay catalysis system featuring the Mannich addition followed by C–C construction and oxydehydrogenation is described. The zirconocene dichloride and trimellitic acid synergic catalysis triggered the Mannich addition and C–C bond construction reactions, while CuO allowed relay catalysis for oxydehydrogenation. This novel strategy demonstrated superior activity for the

  介绍了一种新的三重合作和中继催化系统，其特征是添加了曼尼希（Mannich），然后进行了CC结构和氧脱氢。二氯化锆和偏苯三酸的协同催化作用引发了曼尼希加成反应和CC键的构建反应，而CuO允许中继催化氧化脱氢反应。这种新颖的策略证明了从市售苯胺，醛和酮合成取代喹啉的优异活性。在温和的反应条件下，以32％的实例合成了相应的取代喹啉，产率为90-96％。机理研究证实了一种新型的锆茂-布朗斯台德酸配合物，其在原位生成并充当活性催化剂。
• Microwave-Assisted One-Pot Synthesisof 2,4-Disubstituted Quinolines under Solvent-Free Conditions
  作者：J. S. Yadav、B. V. Reddy、R. Srinivasa Rao、V. Naveenkumar、K. Nagaiah

  DOI：10.1055/s-2003-40531

  日期：——

  derived in situ from aryl aldehydes and aryl amines undergo smoothly, cyclization with alkynes on the surface of montmorillonite clay impregnated with copper(I) bromide under solvent-free conditions to produce 2,4-disubstituted quinolines in high yields with excellent selectivity. The reaction rates and yields are significantly improved by employing microwave irradiation.

  芳基醛和芳胺原位衍生的芳族亚胺在无溶剂条件下与溴化铜 (I) 浸渍的蒙脱土表面上的炔烃进行平稳环化反应，以高收率和优异的选择性制备 2,4-二取代喹啉。通过采用微波照射，反应速率和产率显着提高。