5,7-dimethylquinoline | 20150-89-4

• 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: 5,7-dimethylquinoline
• 英文别名: 5,7-Dimethyl-chinolin；Quinoline, 5,7-dimethyl-
• CAS: 20150-89-4
• 化学式: C₁₁H₁₁N
• mdl: MFCD18448802
• 分子量: 157.215
• InChiKey: MMOMGICWOPOOGD-UHFFFAOYSA-N

物化性质

• 熔点：
  22 °C
• 沸点：
  273-275 °C
• 密度：
  1.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,7-dimethylquinoline 在 乙醇 、 sodium 、 1-溴-3-氯丙烷 作用下， 生成 3,5-dimethyljulolidine
  参考文献：
  名称：

  8-aminolilolidines and 9-aminojulolidines and their addition salts and developer compositions containing the same

  摘要：

  公开号：

  US02707681A1
• 作为产物：
  描述：

  1-氨基-3,5-二甲苯 在 吡啶 、 copper(l) iodide 、 copper(I) bromide 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 32.0h， 生成 5,7-dimethylquinoline
  参考文献：
  名称：

  Copper-Promoted Tandem Reaction of Azobenzenes with Allyl Bromides via N═N Bond Cleavage for the Regioselective Synthesis of Quinolines

  摘要：

  A copper-promoted tandem reaction of a variety of azobenzenes and allyl bromides via N=N bond cleavage to regioselectively construct quinoline derivatives has been developed. The azobenzenes act as not only construction units but also an oxidant for quinoline formation.

  DOI：

  10.1021/acs.orglett.5b03009

文献信息

• Ruthenium-catalyzed formation of quinolines<i>via</i>reductive cyclization of nitroarenes with tris(3-hydroxypropyl)amine in an aqueous medium
  作者：Chan Sik Cho、Na Young Lee、Heung-Jin Choi、Tae-Jeong Kim、Sang Chul Shim

  DOI：10.1002/jhet.5570400530

  日期：2003.9

  Nitroarenes react with tris(3-hydroxypropyl)amine in an aqueous medium (dioxane/H2O) at 180° in the presence of a catalytic amount of a ruthenium catalyst and tin(II) chloride along with isopropanol as hydrogen donor to afford the corresponding quinolines in good yields. The presence of tin(II) chloride is essential for the formation of quinolines. A reaction pathway involving initial reduction of

  在催化量的钌催化剂和氯化锡（II）以及作为氢供体的异丙醇的存在下，硝基芳烃与三（3-羟丙基）胺在水性介质（二恶烷/ H 2 O）中于180°反应相应的喹啉，收率很高。氯化锡（II）的存在对于喹啉的形成至关重要。反应途径包括将硝基芳烃初始还原为苯胺，丙醇基团从三（3-羟丙基）胺转移至苯胺以形成3-苯胺基-1-丙醇，苯胺被3-苯胺基-1-丙醇进行N-烷基化以形成1 1,3-二苯并丙烷和1,3-二苯并丙烷的分子内杂环化被提议用于该催化过程。
• Reduction of nitroarenes followed by propanol group transfer from tris(3-hydroxypropyl)- amine and cyclization leading to quinolines under heterogeneous PdC catalysis
  作者：Chan Sik Cho、Tae Gyun Kim、Nam Sik Yoon

  DOI：10.1002/aoc.1596

  日期：——

  Nitroarenes having electron‐donating or ‐withdrawing substituents are reduced to anilines and cyclized with tris(3‐hydroxypropyl)amine in the presence of a catalytic amount of PdC along with tin(II) chloride and isopropanol in dioxane‐H2O medium to give the corresponding quinolines in good to excellent yields. Copyright © 2009 John Wiley & Sons, Ltd.

  带有给电子或吸电子取代基的硝基芳烃在二恶烷H 2 O介质中，在催化量的PdC以及氯化锡（II）和氯化锡（异丙基）存在下，被三（3-羟丙基）胺还原为苯胺并环化。得到相应的喹啉，收率好至极好。版权所有©2009 John Wiley＆Sons，Ltd.
• Ruthenium-catalyzed synthesis of quinolines<i>via</i>reductive heteroannulation of nitroarenes with 3-amino-1-propanols
  作者：Chan Sik Cho、Tae Kyung Kim、Tae-Jeong Kim、Sang Chul Shim、Nam Sik Yoon

  DOI：10.1002/jhet.5570390207

  日期：2002.3

  Nitroarenes are reductively cyclized with 3-amino-1-propanols in dioxane/H2O in the presence of a ruthenium catalyst and tin(II) chloride dihydrate together with isopropanol to afford the corresponding quinolines. A reaction pathway involving initial reduction of nitroarenes to anilines, propanol group transfer from 3-amino-1-propanols to anilines, N-alkylation of anilines by 3-anilino-1-propanols

  在钌催化剂和二水合氯化锡（II）和异丙醇的存在下，将硝基芳烃与3-氨基-1-丙醇在二恶烷/ H 2 O中还原环化，得到相应的喹啉。提出了一种将硝基芳烃还原为苯胺，丙醇基团从3-氨基-1-丙醇转移至苯胺，苯胺被3-苯胺基-1-丙醇进行N-烷基化和1,3-二苯胺丙烷杂环化反应的反应途径。
• From Anilines to Quinolines: Iodide- and Silver-Mediated Aerobic Double C−H Oxidative Annulation-Aromatization
  作者：Jiwei Wu、Zhixiong Liao、Dong Liu、Chien-Wei Chiang、Zheng Li、Zhonghao Zhou、Hong Yi、Xu Zhang、Zixin Deng、Aiwen Lei

  DOI：10.1002/chem.201703218

  日期：2017.11.13

  Quinoline synthesis from easily accessible raw materials such as anilines is a valuable and meaningful task. Herein, we communicate an iodide‐ and silver‐mediated C−H/C−H oxidative annulation–aromatization between anilines and allyl alcohols. This protocol provides a direct route to the synthesis of quinoline derivatives from inexpensive commodities. Various kinds of anilines, even heterocyclic anilines

  由苯胺等容易获得的原料合成喹啉是一项宝贵而有意义的任务。在本文中，我们传达了苯胺和烯丙醇之间碘化物和银介导的CH / CH氧化环化-芳香化反应。该协议提供了从廉价商品合成喹啉衍生物的直接途径。各种苯胺，甚至杂环苯胺，都是可行的底物，可产生高收率的相应多取代喹啉。
• [EN] INHIBITORS OF HEPATITIS C VIRUS<br/>[FR] INHIBITEURS DU VIRUS DE L'HÉPATITE C
  申请人：GILEAD SCIENCES INC

  公开号：WO2014008285A1

  公开（公告）日：2014-01-09

  Compounds of Formula I are disclosed, As well as pharmaceutically acceptable salts thereof. Methods of using said compounds and pharmaceutical compositions containing said compounds are also disclosed.

  化合物I的结构已经披露，以及其药用盐。还披露了使用这些化合物的方法和含有这些化合物的药物组合物。