5,7-Diiodo-8-(2-methylprop-2-enoxy)quinoline | 1416989-00-8

• 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-Diiodo-8-(2-methylprop-2-enoxy)quinoline
• CAS: 1416989-00-8
• 化学式: C₁₃H₁₁I₂NO
• 分子量: 451.045
• InChiKey: KBXWKDYWRMVPMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  5,7-Diiodo-8-(2-methylprop-2-enoxy)quinoline 在 acetylacetonatodicarbonylrhodium(l) 、 sodium tetrahydroborate 、 2-(diphenylphosphoryl)benzoic acid 、 氢气 、 magnesium sulfate 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 N-[(4-chlorophenyl)methyl]-4-[(5,7-diiodo-8-quinolyl)oxy]-3-methyl-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：

  5,7-二碘-8-羟基喹啉 、 3-溴-2-甲基丙烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 生成 5,7-Diiodo-8-(2-methylprop-2-enoxy)quinoline
  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

• Harnessing Reversible Oxidative Addition: Application of Diiodinated Aromatic Compounds in the Carboiodination Process
  作者：David A. Petrone、Matthias Lischka、Mark Lautens

  DOI：10.1002/anie.201304923

  日期：2013.9.27

  simultaneous convergent intramolecular carboiodination/intermolecular Heck reaction of various diiodoarenes were developed. The ability of the Pd0/QPhos catalyst/ligand combination to undergo reversible oxidative addition allows these reactions to proceed well, thus increasing both the appeal and utility of this class of substrates in site‐selective cross‐coupling reactions.

  I为I：开发了各种二碘代芳烃的分子内碳碘化和同时收敛的分子内碳碘化/分子间Heck反应的条件。Pd 0 / QPhos催化剂/配体组合进行可逆氧化加成的能力使这些反应顺利进行，从而提高了这类底物在定点交叉偶联反应中的吸引力和实用性。