2-氯-6-甲基喹啉-3-甲酸甲酯 | 773874-60-5

• 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: 2-氯-6-甲基喹啉-3-甲酸甲酯
• 英文名称: methyl 2-chloro-6-methylquinoline-3-carboxylate
• CAS: 773874-60-5
• 化学式: C₁₂H₁₀ClNO₂
• 分子量: 235.67
• InChiKey: YLADGSFINZQJJI-UHFFFAOYSA-N

物化性质

• 沸点：
  341.3±37.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氯-6-甲基喹啉-3-甲酸甲酯 在 iron(III) chloride 、 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 3-(butylselanyl)-8-methyl-2-phenyl-5H-selenopheno[2',3':5,6]pyrano[4,3-b]quinolin-5-one
  参考文献：
  名称：

  氯化铁 (III) 和二烷基二硒化物促进分子内级联环化，从而合成硒酚稠合喹啉基杂环

  摘要：

  在这封信中，描述了一种方便合成硒酚稠合喹啉基杂环的新途径。三氯化铁和二烷基二硒化物产生的 6-甲基-2-(苯基丁-1,3-二炔-1-基)喹啉-3-羧酸甲酯的分子内级联环化以良好的收率得到基于硒酚稠合的喹啉的杂环衍生物。

  DOI：

  10.1016/j.tetlet.2022.153907
• 作为产物：
  描述：

  乙烷,三氯氟- 在 碘 、 potassium carbonate 、 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 生成 2-氯-6-甲基喹啉-3-甲酸甲酯
  参考文献：
  名称：

  Synthesis and Herbicidal Activity of Triketone–Quinoline Hybrids as Novel 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

  摘要：

  4-Hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD) is one of the most important targets for herbicide discovery. In the search for new HPPD inhibitors with novel scaffolds, triketone-quinoline hybrids were designed and subsequently optimized on the basis of the structure -activity relationship (SAR) studies. Most of the synthesized compounds displayed potent inhibition of Arabidopsis thaliana HPPD (AtHPPD), and some of them exhibited broad-spectrum and promising herbicidal activity at the rate of 150 g ai/ha by postemergence application. Most promisingly, compound III-1, 3-hydroxy-2-(2-methoxy-7-(methylthio)quinoline-3-carbonyl)cyclohex-2-enone (K-i = 0.009 mu M, AtHPPD), had broader spectrum of weed control than mesotrione. Furthermore, compound III-1 was much safer to maize at the rate of 150 g ai/ha than mesotrione, demonstrating its great potential as herbicide for weed control in maize fields. Therefore, triketone-quinoline hybrids may serve as new lead structures for novel herbicide discovery.

  DOI：

  10.1021/acs.jafc.5b01530

文献信息

• N-Heterocyclic Carbene Catalyzed Cross Dehydrogenative Coupling of Aldehydes with Methanol: Combined Use of Eosin Y and Hexachloroethane
  作者：Hideto Miyabe、Eito Yoshioka、Hiroki Takahashi、Akane Kubo、Miki Ohno、Fuuka Watanabe、Rino Shiono、Yuuki Miyazaki

  DOI：10.1055/a-1918-4406

  日期：2022.12

  Cross dehydrogenative coupling of aldehydes with methanol was investigated under organocatalytic conditions based on the cooperation­ between N-heterocyclic carbene and eosin Y·Na as an organophotocatalys­t. The combined use of eosin Y·Na and hexachloro­ethane (C2Cl6) was the effective method for the oxidative esterification of various aldehydes, because the oxidation steps are promoted by two pathways

  基于N-杂环卡宾与曙红Y·Na作为有机光催化剂的协同作用，在有机催化条件下研究了醛与甲醇的交叉脱氢偶联。曙红Y·Na和六氯乙烷（C 2 Cl 6）的联合使用是各种醛氧化酯化的有效方法，因为氧化步骤由与活化光催化剂和C 2 Cl 6相关的两条途径促进。相比之下，曙红 Y·Na 和溴三氯甲烷 (BrCCl 3 ) 的联合使用仅对简单的肉桂醛衍生物的氧化酯化有效，其中 BrCCl 3促进作为溴化试剂向自由基中间体的氧化。
• Development of N-Doped Carbon-Supported Cobalt/Copper Bimetallic Nanoparticle Catalysts for Aerobic Oxidative Esterifications Based on Polymer Incarceration Methods
  作者：Tomohiro Yasukawa、Xi Yang、Shu̅ Kobayashi

  DOI：10.1021/acs.orglett.8b02118

  日期：2018.9.7

  Heterogeneous nitrogen-doped carbon-incarcerated cobalt/copper bimetallic nanoparticle (NP) catalysts, prepared from nitrogen-containing polymers, were developed, and an efficient catalytic process for aerobic oxidative esterification was achieved in the presence of a low loading (1 mol %) of catalyst that could be reused and easily reactivated. This protocol enabled diverse conditions for the bimetallic NP formation step to be screened, and significant rate acceleration by inclusion of a copper dopant was discovered. The catalytic activity of the bimetallic Co/Cu catalysts is much higher than that for cobalt catalysts reported to date and is even comparable with noble-metal NP catalysts.
• An economical nucleophilic route toward facile synthesis of pyrano[4,3-b]quinolin-1-ones via 6-endo-dig cyclization of o-alkynylquinoline esters
  作者：Neha Sharma、Mrityunjaya Asthana、Durgesh Nandini、R.P. Singh、Radhey M. Singh

  DOI：10.1016/j.tet.2012.12.068

  日期：2013.2

  Metal-free facile synthesis of pyrano[4,3-b]quinoline-1-ones is described from methyl 2-arylethynyl-quinoline-3-carboxylates via intramolecular cyclization in excellent yields. The cyclization reactions are facilitated using cheap and easily available KOH base in MeOH. The reaction conditions did not require dry solvent, inert atmosphere, and avoid further column chromatography purification of the products. These compounds could be further used as building blocks for the synthesis of 2H-benzo[b][1,6]naphthyridin-1-one and 1-chloro-benzo[b][1,6]naphthyridines. (C) 2013 Elsevier Ltd. All rights reserved.
• Srivastava, Ambika; Singh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 9, p. 1868 - 1875
  作者：Srivastava, Ambika、Singh

  DOI：——

  日期：——