6-chloro-2-(thiophen-2-yl)quinoline | 944817-29-2

• 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-chloro-2-(thiophen-2-yl)quinoline
• 英文别名: 6-Chloro-2-thiophen-2-ylquinoline
• CAS: 944817-29-2
• 化学式: C₁₃H₈ClNS
• 分子量: 245.732
• InChiKey: JUEPXSIZYGLIJT-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：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 sulfur 作用下， 反应 0.17h， 生成 6-chloro-2-(thiophen-2-yl)quinoline
  参考文献：
  名称：

  Simple C-2-Substituted Quinolines and their Anticancer Activity

  摘要：

  对16种C-2取代的喹啉进行了人癌细胞系(MCF-7，H-460和SF-268)和正常细胞系(Vero和THP-1)的测试。初步结果表明，2-α呋喃基和2-γ吡啶基喹啉衍生物1，13和14对三种人癌细胞系具有活性，同时对正常细胞没有细胞毒性效应。生物活性和SAR结果与使用在线可用软件通过计算确定的不同的分子描述符进行了比较，试图展示这些喹啉衍生物可能的作用模式的关联。

  DOI：

  10.2174/157018012801319544

文献信息

• Visible-light-induced photoxidation-Povarov cascade reaction: synthesis of 2-arylquinoline through alcohol and <i>N</i>-benzylanilines under mild conditions <i>via</i> Ag/g-C₃N₄ nanometric semiconductor catalyst
  作者：Peng Wang、Xiaowen Wang、Xiyu Niu、Li Zhu、Xiaoquan Yao

  DOI：10.1039/d0cc00885k

  日期：——

  Ag/g-C3N4 nanometric semiconductor as the photocatalyst, 2-arylquinolines were synthesized through a photoxidation-Povarov cascade reaction of N-benzylanilines and alcohols under visible light irradiation. Under the blue light of a 3 W LED, good yields were achieved for various substrates in oxygen at room temperature. This methodology provides a green and mild alternative for the formation of 2-arylquinoline

  以Ag / g-C3N4纳米半导体为光催化剂，在可见光照射下，通过N-苄基苯胺和醇的光氧化-Povarov级联反应合成了2-芳基喹啉。在3 W LED的蓝光下，室温下在氧气中各种衬底的产率都很高。该方法为2-芳基喹啉衍生物的形成提供了绿色和温和的替代方法。值得注意的是，Ag / g- 纳米复合材料可以方便地回收并以令人满意的产率重复使用数次。
• Three-Component Povarov Reaction with Alcohols as Alkene Precursors: Efficient Access to 2-Arylquinolines
  作者：Xinjian Li、Qi Xing、Pan Li、Jingjing Zhao、Fuwei Li

  DOI：10.1002/ejoc.201601343

  日期：2017.1.18

  An atom-economic and efficient approach to the synthesis of 2-arylquinolines has been developed. The protocol involves an iron-catalysed cascade N-alkylation/aerobic oxidation/Povarov reaction, and the desired quinolines were prepared in moderate to excellent yields from readily accessible anilines, aldehydes, and EtOH/nPrOH, with water as the only side-product. The aniline substrates also act as a

  已开发出一种原子经济且有效的合成 2-芳基喹啉的方法。该协议涉及铁催化的级联 N-烷基化/有氧氧化/Povarov 反应，所需的喹啉是从易于获得的苯胺、醛和 EtOH/nPrOH 中以中等至极好的收率制备的，水作为唯一的副产品。苯胺底物还通过原位 N-烷基化/氧化过程充当 EtOH/nPrOH 的可回收转移介质。这使得 EtOH/nPrOH 成为一种经济且环保的烯烃前体和溶剂。
• Molybdenum-Catalyzed Sustainable Friedländer Synthesis of Quinolines
  作者：Rubén Rubio-Presa、Samuel Suárez-Pantiga、María R. Pedrosa、Roberto Sanz

  DOI：10.1002/adsc.201800278

  日期：2018.6.5

  Polysubstituted quinolines have been efficiently synthesized from nitroarenes and glycols, as reducing agents, under dioxomolybdenum(VI)‐catalysis. Interestingly, the waste reduction byproduct is incorporated into the final heterocycle. This method represents an efficient and sustainable variant of the Friedländer synthesis of quinolines.

  在二氧钼钼（VI）催化下，已经有效地由硝基芳烃和乙二醇作为还原剂合成了多取代的喹啉。有趣的是，减少废物的副产物被掺入了最终的杂环中。该方法代表了Friedländer喹啉合成的高效且可持续的变体。
• Cyclometalated iridium complexes-catalyzed acceptorless dehydrogenative coupling reaction: construction of quinoline derivatives and evaluation of their antimicrobial activities
  作者：Hongling Shui、Yuhong Zhong、Renshi Luo、Zhanyi Zhang、Jiuzhong Huang、Ping Yang、Nianhua Luo

  DOI：10.3762/bjoc.18.159

  日期：——

  dehydrogenative coupling (ADC) reaction is an efficient method for synthesizing quinoline and its derivatives. In this paper, various substituted quinolines were synthesized from 2-aminobenzyl alcohols and aryl/heteroaryl/alkyl secondary alcohols in one pot via a cyclometalated iridium-catalyzed ADC reaction. This method has some advantages, such as easy availability of raw materials, mild reaction conditions

  无受体脱氢偶联（ADC）反应是合成喹啉及其衍生物的有效方法。本文以2-氨基苄醇和芳基/杂芳基/烷基仲醇为原料，通过环金属化铱催化的ADC反应，在一锅中合成了多种取代的喹啉。该方法具有原料易得、反应条件温和、底物范围广、环境友好等优点，符合绿色化学原理。此外，具有低催化剂负载的克级实验提供了获得合适量的芳基/杂芳基喹诺酮类药物的潜力。此外，还对合成的喹啉的抗菌和抗真菌活性进行了体外评价，3ab、3ad和3ah对革兰氏阳性菌和化合物3ck对白色念珠菌的作用优于参考药物诺氟沙星。
• In vitro antifungal activity of polyfunctionalized 2-(hetero)arylquinolines prepared through imino Diels–Alder reactions
  作者：Carlos M. Meléndez Gómez、Vladimir V. Kouznetsov、Maximiliano A. Sortino、Sandra L. Álvarez、Susana A. Zacchino

  DOI：10.1016/j.bmc.2008.07.079

  日期：2008.9

  Diverse polyfunctionalized quinolines, easily prepared using Lewis acid-catalyzed imino Diels-Alder reactions between corresponding aldimines, were tested for antifungal properties against standardized as well as clinical isolates of clinically important fungi. Among them, 4-pyridyl derivatives displayed the best activities mainly against dermatophytes. The activity appears not to be related neither to the lipophilicity nor to the basicity of compounds. (C) 2008 Elsevier Ltd. All rights reserved.