5-chloro-7-(2-methyl-2-propenyl)quinolin-8-ol | 1416989-04-2

• 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-chloro-7-(2-methyl-2-propenyl)quinolin-8-ol
• 英文别名: 5-Chloro-7-(2-methylprop-2-enyl)quinolin-8-ol；5-chloro-7-(2-methylprop-2-enyl)quinolin-8-ol
• CAS: 1416989-04-2
• 化学式: C₁₃H₁₂ClNO
• 分子量: 233.697
• InChiKey: ZAZYCHFFOOKDTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chloro-7-(2-methyl-2-propenyl)quinolin-8-ol 在 (acetylacetonato)dicarbonylrhodium (l) 、 BINAPa 、 氢气 、 溶剂黄146 作用下， 以 甲醇 、 甲苯 为溶剂， 20.0~80.0 ℃ 、2.0 MPa 条件下， 反应 26.0h， 生成 5-chloro-7-(4-diethylamino-2-methylbutyl)quinolin-8-ol
  参考文献：
  名称：

  Synthesis and antiplasmodial evaluation of novel (4-aminobutyloxy)quinolines

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2012.10.094
• 作为产物：
  描述：

  一氧化碳 、 5-Chloro-8-(2-methylallyloxy)quinoline 在 (acetylacetonato)dicarbonylrhodium (l) 、 氢气 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 甲苯 为溶剂， 80.0 ℃ 、2.0 MPa 条件下， 反应 18.0h， 以99%的产率得到5-chloro-7-(2-methyl-2-propenyl)quinolin-8-ol
  参考文献：
  名称：

  Synthesis and antiplasmodial evaluation of novel (4-aminobutyloxy)quinolines

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2012.10.094

文献信息

• 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.