6-hydroxy-3-pentyl-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-hydroxy-3-pentyl-2-phenylquinoline
• 英文别名: 3-pentyl-2-phenylquinolin-6-ol
• 化学式: C₂₀H₂₁NO
• 分子量: 291.393
• InChiKey: AULJSIVXVGJWKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  正庚醇 、 4-苄烯氨基苯酚 在 反式-巴豆腈(含有约20的顺式同分异构体) 、 三氟乙酸 作用下， 反应 3.0h， 以52%的产率得到6-hydroxy-3-pentyl-2-phenylquinoline
  参考文献：
  名称：

  通过（生物）可用醇和氨基芳烃的交叉脱氢偶联，温和高效地合成取代的喹啉

  摘要：

  AbstractA ruthenium‐catalysed dehydrogenative cross‐coupling of primary alcohols and imines in the presence of TFA provided a library of differently substituted quinolines. Imines can be prepared in situ from various anilines and several benzyl alcohols using a ruthenium‐catalysed hydrogen‐transfer procedure. Without changing the catalyst, quinolines can be obtained in moderate to good yields by adding various primary alcohols in the presence of TFA (30 mol%) via a “telescopic” protocol. The use of alcohols, the absence of strong oxidants and the diversity of potential starting materials make this modern version of the Skraup reaction superior to most of the conventional quinoline syntheses.magnified image

  DOI：

  10.1002/adsc.201400815

文献信息

• Practical and Simple Synthesis of Substituted Quinolines by an HCl−DMSO System on a Large Scale:  Remarkable Effect of the Chloride Ion
  作者：Shin-ya Tanaka、Makoto Yasuda、Akio Baba

  DOI：10.1021/jo052004y

  日期：2006.1.1

  A variety of substituted quinolines are synthesized from imines and enolizable carbonyl compounds under aerobic conditions, in which only water is a byproduct. In DMSO, a catalytic amount of HCl activates carbonyl compounds quite effectively to give the quinolines. A simple and practical procedure is demonstrated on a large scale.
• A Mild and Efficient Synthesis of Substituted Quinolines<i>via</i>a Cross-Dehydrogenative Coupling of (Bio)available Alcohols and Aminoarenes
  作者：Manuel G. Mura、Suvi Rajamäki、Lidia De Luca、Elena Cini、Andrea Porcheddu

  DOI：10.1002/adsc.201400815

  日期：2015.2.9

  AbstractA ruthenium‐catalysed dehydrogenative cross‐coupling of primary alcohols and imines in the presence of TFA provided a library of differently substituted quinolines. Imines can be prepared in situ from various anilines and several benzyl alcohols using a ruthenium‐catalysed hydrogen‐transfer procedure. Without changing the catalyst, quinolines can be obtained in moderate to good yields by adding various primary alcohols in the presence of TFA (30 mol%) via a “telescopic” protocol. The use of alcohols, the absence of strong oxidants and the diversity of potential starting materials make this modern version of the Skraup reaction superior to most of the conventional quinoline syntheses.magnified image