6-氯喹啉-2-羧酸乙酯 | 860190-32-5

• 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
• 中文名称: 6-氯喹啉-2-羧酸乙酯
• 英文名称: ethyl 6-chloroquinoline-2-carboxylate
• 英文别名: 6-chloro-quinoline-2-carboxylic acid ethyl ester；6-Chlor-chinolin-2-carbonsaeure-aethylester；Ethyl 6-chloroquinoline-2-carboxylate
• CAS: 860190-32-5
• 化学式: C₁₂H₁₀ClNO₂
• 分子量: 235.67
• InChiKey: RKSFTJRALUORNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  6-氯喹啉-2-羧酸乙酯 在 乙醚 、 甲基溴化镁 作用下， 生成 6-chloro-2-isopropenyl-quinoline
  参考文献：
  名称：

  Monomers and Polymers. V. Vinylpyridines and Vinylquinolines^1,2

  摘要：

  DOI：

  10.1021/ja01187a020
• 作为产物：
  描述：

  2-碘-4-氯苯胺 在 哌啶 、 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 sodium sulfate 、 二乙胺 、 三氟乙酸 、 copper(ll) bromide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 6-氯喹啉-2-羧酸乙酯
  参考文献：
  名称：

  Copper-Catalyzed [5 + 1] Annulation of 2-Ethynylanilines with an N,O-Acetal Leading to Construction of Quinoline Derivatives

  摘要：

  A novel copper-catalyzed [5 + 1] annulation of 2-ethynylanilines with an N,O-acetal, which functioned as a Cl part, leading to the preparation of quinoline derivatives with an ester substituent on the 2-position is described. A combination of CuBr2 and trifluoroacetic acid (TFA) promoting [5 + 1] annulation of the 2-ethynylaniline with ethyl glyoxylate is also demonstrated.

  DOI：

  10.1021/ol203360g

文献信息

• Eco-efficient synthesis of 2-quinaldic acids from furfural
  作者：Minghao Li、Xiaohan Dong、Na Zhang、François Jérôme、Yanlong Gu

  DOI：10.1039/c9gc02206f

  日期：——

  through photooxidation of furfural and a consecutive ring-opening alcoholysis; (ii) cyclization of ethyl 4,4-diethoxycrotonate with aniline, and (iii) hydrolysis of the generated ethyl quinaldate. This new method not only avoids the use of toxic potassium cyanide but also meets many salient features of green chemistry, such as the use of bio-based feedstocks, environmentally benign metal-free conditions and

  喹啉酸是重要的精细化学品。如今，合成喹啉酸的工业方法严重依赖于基于Reissert反应建立的三步法，但是该过程涉及使用剧毒的氰化钾。本文实现了4,4-二乙氧基巴豆酸乙酯对苯胺的新型环化反应，得到的喹啉乙酯收率高。基于该反应，开发了一种生态高效的制备喹啉酸的方法，该方法涉及以下三个步骤：（i）通过糠醛的光氧化和连续的开环醇解合成4,4-二乙氧基巴豆酸乙酯；（ii）用苯胺将4，4-二乙氧基巴豆酸乙酯环化，和（iii）产生的喹啉酸乙酯水解。
• Copper-catalysed aerobic oxidative esterification of N-heteroaryl methanes with alcohols
  作者：Min Liu、Tieqiao Chen、Shuang-Feng Yin

  DOI：10.1039/c5cy02069g

  日期：——

  Efficient copper-catalysed aerobic oxidative esterification of N-heteroaryl methanes with alcohols has been developed. A variety of N-heteroaryl esters including those with functional groups are produced in good to excellent yields under the present reaction conditions.

  已经开发出N-杂芳基甲烷与醇的铜催化的好氧氧化酯化反应。在本反应条件下，以良好或优异的产率制备了各种N-杂芳基酯，包括具有官能团的N-杂芳基酯。
• A Core‐Linker‐Polyamine (CLP) Strategy Enables Rapid Discovery of Antileishmanial Aminoalkylquinolinecarboxamides That Target Oxidative Stress Mechanism
  作者：Archana P. Shah、Neha Hura、Neerupudi Kishore Babu、Nibedita Roy、Vajja Krishna Rao、Anindita Paul、Pradyot Kumar Roy、Sushma Singh、Sankar K. Guchhait

  DOI：10.1002/cmdc.202200109

  日期：2022.8.17

  Exploring potent antileishmanial chemotypes: A unique core-linker-polyamine-strategy was considered for discovery of antileishmanial agents. Aminoalkyl-quinolinecarboxamides were synthesized by establishment of a synthetic route. The compounds showed significant antileishmanial activity, poor cytotoxicity, enhanced intracellular level of ROS in mitochondria and high morphological changes in the promastigotes

  探索有效的抗寄生虫化学型：考虑采用独特的核心-接头-多胺策略来发现抗寄生虫药物。通过建立合成路线合成了氨基烷基-喹啉甲酰胺。这些化合物显示出显着的杀虫活性、较差的细胞毒性、线粒体中 ROS 的细胞内水平增强和前鞭毛体的高度形态变化。鉴定了对活性重要的药效团。
• Radical cation salt induced Povarov reaction between iminoethyl glyoxylate and N-vinylamides: synthesis of quinoline-2-carboxylate derivatives
  作者：Xiaodong Jia、Chang Qing、Congde Huo、Fangfang Peng、Xicun Wang

  DOI：10.1016/j.tetlet.2012.10.097

  日期：2012.12

  A domino process between iminoethyl glyoxylate and N-vinylamides was achieved under the catalytic radical cation salt induced conditions, producing a series of quinoline-2-carboxylates. N-Vinylamides were involved as an acetylene equivalent. A possible mechanism was proposed to rationalize the formation of the products. (C) 2012 Elsevier Ltd. All rights reserved.
• Monomers and Polymers. V. Vinylpyridines and Vinylquinolines^1,2
  作者：G. Bryant Bachman、D. Donald Micucci

  DOI：10.1021/ja01187a020

  日期：1948.7