5-allyloxyquinoline | 7652-22-4

• 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-allyloxyquinoline
• 英文别名: 5-prop-2-enoxyquinoline
• CAS: 7652-22-4
• 化学式: C₁₂H₁₁NO
• 分子量: 185.225
• InChiKey: IHIYCHHEHMVXGD-UHFFFAOYSA-N

物化性质

• 沸点：
  120-124 °C(Press: 0.7 Torr)
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-allyloxyquinoline 在 acetylacetonatodicarbonylrhodium(l) 、 2-(diphenylphosphoryl)benzoic acid 、 氢气 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 N,N-diethyl-4-(5-quinolyloxy)butan-1-amine
  参考文献：
  名称：

  Evaluation of (4-aminobutyloxy)quinolines as a novel class of antifungal agents

  摘要：

  Antifungal assessment of eighteen 5-, 6- and 8-(4-aminobutyloxy)quinolines revealed a significant susceptibility of the tested fungi and yeast strains (Candida albicans, Rhodotorula bogoriensis, Aspergillus flavus and Fusarium solani) toward different halo-substituted 8-(4-aminobutyloxy)quinolines. The six most potent compounds displayed antifungal activities similar to those of established antifungal agents such as Amphotericin B, Fluconazole and Itraconazole, and one representative also showed a promising broad-spectrum antifungal profile. The introduction of an aminoalkoxy side chain at the 8-position of a halo-substituted quinoline core might thus provide a new class of lead structures in the search for novel antifungal agents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.014
• 作为产物：
  描述：

  5-羟基喹啉 、 3-溴丙烯 在 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.17h， 以92%的产率得到5-allyloxyquinoline
  参考文献：
  名称：

  QUINOLINE DERIVATIVES FOR INHIBITING HISTONE METHYLTRANSFERASES AND USE THEREOF

  摘要：

  本公开涉及一种喹啉衍生物，其抑制特定于组蛋白分子H3K9的组蛋白甲基转移酶（ESET/SETDB1）的活性或其药用盐，以及其用途。

  公开号：

  US20170354650A1

文献信息

• [EN] QUINOLINE 3-AMINO CHROMAN DERIVATIVES<br/>[FR] AMINO-PYRANOQUINOLEINES EN TANT QU'INHIBITEURS DE RECAPTAGE DE LA SEROTONINE ET AGONISTES DE RECEPTEURS 5-HT1A
  申请人：WYETH CORP

  公开号：WO2004099214A1

  公开（公告）日：2004-11-18

  Quinoline 3 -amino chroman derivatives and compositions containing such compounds are disclosed. Methods for using the quinoline 3-amino chroman derivatives and compositions containing such compounds in the treatment of serotonin disorders are disclosed. Also disclosed are processes for preparing quinoline 3-amino chroman derivatives.

  揭示了喹啉3-氨基色苷衍生物和含有这种化合物的组合物。还揭示了使用喹啉3-氨基色苷衍生物和含有这种化合物的组合物来治疗血清素紊乱的方法。还揭示了制备喹啉3-氨基色苷衍生物的方法。
• Quinoline 3-amino chroman derivatives
  申请人：Hatzenbuhler Theriault Nicole

  公开号：US20050004157A1

  公开（公告）日：2005-01-06

  Quinoline 3-amino chroman derivatives and compositions containing such compounds are disclosed. Methods for using the quinoline 3-amino chroman derivatives and compositions containing such compounds in the treatment of serotonin disorders are disclosed. Also disclosed are processes for preparing quinoline 3-amino chroman derivatives.

  本发明公开了喹啉3-氨基色基衍生物和含有这种化合物的组合物。公开了使用喹啉3-氨基色基衍生物和含有这种化合物的组合物治疗血清素失调的方法。还公开了制备喹啉3-氨基色基衍生物的方法。
• QUINOLINE 3-AMINO CHROMAN DERIVATIVES
  申请人：Hatzenbuhler Theriault Nicole

  公开号：US20070191417A1

  公开（公告）日：2007-08-16

  Quinoline 3-amino chroman derivatives and compositions containing such compounds are disclosed. Methods for using the quinoline 3-amino chroman derivatives and compositions containing such compounds in the treatment of serotonin disorders are disclosed. Also disclosed are processes for preparing quinoline 3-amino chroman derivatives.

  本文揭示了喹啉3-氨基色基衍生物和含有这种化合物的组合物。还揭示了利用喹啉3-氨基色基衍生物和含有这种化合物的组合物治疗血清素失调的方法。同时，还揭示了制备喹啉3-氨基色基衍生物的过程。
• 630. Some alkylquinoline-5: 8-quinones
  作者：R. Long、K. Schofield

  DOI：10.1039/jr9530003161

  日期：——
• Synthesis and antiplasmodial evaluation of novel (4-aminobutyloxy)quinolines
  作者：Stéphanie Vandekerckhove、Christian Müller、Dieter Vogt、Carmen Lategan、Peter J. Smith、Kelly Chibale、Norbert De Kimpe、Matthias D’hooghe

  DOI：10.1016/j.bmcl.2012.10.094

  日期：2013.1

  A variety of 5-, 6- and 8-(4-aminobutyloxy) quinolines as novel oxygen analogues of known 4- and 8-(4-aminobutylamino)quinoline antimalarial drugs was generated from hydroxyquinolines through a three-step approach with a rhodium-catalyzed hydroformylation as the key step. Antiplasmodial assays of these new quinolines revealed micromolar potency for all representatives against a chloroquine-sensitive strain of Plasmodium falciparum, and three compounds showed submicromolar activity against a chloroquine-resistant strain of P. falciparum with IC50-values ranging between 150 and 680 nM. (C) 2012 Elsevier Ltd. All rights reserved.