N⁴-(7-chloro-2-phenylquinolin-4-yl)-N¹,N¹-diethylpentane-1,4-diamine | 33601-73-9

• 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: N⁴-(7-chloro-2-phenylquinolin-4-yl)-N¹,N¹-diethylpentane-1,4-diamine
• 英文别名: N⁴,N⁴-diethyl-N¹-(7-chloro-2-phenyl-[4]quinolyl)-1-methyl-butanediyldiamine；N⁴,N⁴-Diaethyl-N¹-(7-chlor-2-phenyl-[4]chinolyl)-1-methyl-butandiyldiamin；N4-(7-chloro-2-phenyl-4-quinolyl)-N1,N1-diethyl-pentane-1,4-diamine；4-N-(7-chloro-2-phenylquinolin-4-yl)-1-N,1-N-diethylpentane-1,4-diamine
• CAS: 33601-73-9
• 化学式: C₂₄H₃₀ClN₃
• 分子量: 395.975
• InChiKey: SEDUQYVBGBSJEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氨基-5-二乙基氨基戊烷 在 盐酸 、 palladium diacetate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 copper(I) bromide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.25h， 生成 N⁴-(7-chloro-2-phenylquinolin-4-yl)-N¹,N¹-diethylpentane-1,4-diamine
  参考文献：
  名称：

  Modular Three-Component Synthesis of 4-Aminoquinolines via an Imidoylative Sonogashira/Cyclization Cascade

  摘要：

  We developed a one-pot, two-stage synthetic route to substituted 4-aminoquinolines involving an imidoylative Sonogashira coupling followed by acid-mediated cyclization. This three-component reaction affords pharmaceutically valuable 4-aminoquinolines in a one-pot procedure from readily available starting materials. The reaction tolerates various substituents on the arene as well as the use of secondary and even primary isocyanides. Additionally, the wide tolerance for functionalized isocyanides allows for the one-pot synthesis of various substituted chloroquine analogues as well as other medicinally relevant products.

  DOI：

  10.1021/acs.joc.7b02844

文献信息

• Synthetic Antimalarials. The Preparation of Certain 4-Aminoquinolines¹
  作者：Nathan L. Drake、Hugh J. Creech、John A. Garman、Stuart T. Haywood、Richard M. Peck、John O. van Hook、Edward Walton

  DOI：10.1021/ja01211a021

  日期：1946.7
• Modular Three-Component Synthesis of 4-Aminoquinolines via an Imidoylative Sonogashira/Cyclization Cascade
  作者：Jurriën W. Collet、Kelly Ackermans、Jeffrey Lambregts、Bert U.W. Maes、Romano V.A. Orru、Eelco Ruijter

  DOI：10.1021/acs.joc.7b02844

  日期：2018.1.19

  We developed a one-pot, two-stage synthetic route to substituted 4-aminoquinolines involving an imidoylative Sonogashira coupling followed by acid-mediated cyclization. This three-component reaction affords pharmaceutically valuable 4-aminoquinolines in a one-pot procedure from readily available starting materials. The reaction tolerates various substituents on the arene as well as the use of secondary and even primary isocyanides. Additionally, the wide tolerance for functionalized isocyanides allows for the one-pot synthesis of various substituted chloroquine analogues as well as other medicinally relevant products.