6,8-dicyanoquinoline | 1563017-40-2

• 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: 6,8-dicyanoquinoline
• 英文别名: 6,8-Quinolinedicarbonitrile；quinoline-6,8-dicarbonitrile
• CAS: 1563017-40-2
• 化学式: C₁₁H₅N₃
• 分子量: 179.181
• InChiKey: FISINRLBKYQWJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6,8-dicyano-1,2,3,4-tetrahydroquinoline 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 3.0h， 以75%的产率得到6,8-dicyanoquinoline
  参考文献：
  名称：

  Synthesis of novel cyano quinoline derivatives

  摘要：

  6,8-Dibromo-1,2,3,4-tetrahydroquinoline (2) and 3,6,8-tribromoquinoline (3) were converted into the corresponding cyano derivatives via copper assisted nucleophilic substitution reactions. While bromination of 6-bromo-8-cyanotetrahydroquinoline (11) gave 3,6-dibromo-8-cyanoquinoline (8), the reaction of dicyano-1,2,3,4-tetrahydroquinoline (12) resulted in the formation of an unexpected dimer (15). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.07.092

文献信息

• Simple and convenient preparation of novel 6,8-disubstituted quinoline derivatives and their promising anticancer activities
  作者：Salih ÖKTEN、Osman ÇAKMAK、Ramazan ERENLER、Önem YÜCE、Şaban TEKİN

  DOI：10.3906/kim-1301-30

  日期：——

  A short and easy route is described for 6,8-disubstituted derivatives of quinoline and 1,2,3,4-tetrahydroquinoli- ne from 6,8-dibromoquinolines 2 and 7 by various substitution reactions. While copper-promoted substitution of 6,8-dibromide 2 produced monomethoxides 3 and 4, a prolonged reaction time mainly afforded dimethoxide 6 instead of 5, whose aromatization with DDQ and substitution reaction of dibromide 7 with NaOMe in the presence of CuI also gave rise to dimethoxide 6. Several 6,8-disubstituted quinolines were obtained by treatment of 6,8-dibromoquinoline (7) with n-BuLi followed by trapping with an electrophile [Si(Me)_3Cl, S_2(Me)_2, and DMF]. Furthermore, 7 was also converted to mono and dicyano derivatives. The anticancer activities of compounds 2, 7, 6, 12, 13, 15, and 16 against HeLa, HT29, and C6 tumor cell lines were tested, and 6,8-dibromo-1,2,3,4-tetrahydroquinoline (2) and 6,8-dimethoxyquinoline (6) showed significant anticancer activities against the tumor cell lines.

  通过各种取代反应，描述了从 6,8 二溴喹啉 2 和 7 中制备 6,8 二取代喹啉和 1,2,3,4 四氢喹啉衍生物的简捷路线。铜促进的 6,8 二溴化物 2 的取代反应产生了单甲氧基化合物 3 和 4，但反应时间延长主要产生了二甲氧基化合物 6 而不是 5，其与 DDQ 的芳香化反应以及二溴化物 7 在 CuI 存在下与 NaOMe 的取代反应也产生了二甲氧基化合物 6。用 n-BuLi 处理 6，8-二溴喹啉 (7)，然后用亲电体[Si(Me)_3Cl、S_2(Me)_2 和 DMF]捕集，得到了几种 6，8-二取代的喹啉。此外，7 还被转化为单氰基和二氰基衍生物。测试了化合物 2、7、6、12、13、15 和 16 对 HeLa、HT29 和 C6 肿瘤细胞株的抗癌活性，结果表明 6,8-二溴-1,2,3,4-四氢喹啉（2）和 6,8-二甲氧基喹啉（6）对肿瘤细胞株具有显著的抗癌活性。