2-chloro-7-methylsulfanyl-quinoline-3-carbaldehyde | 73568-30-6

• 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: 2-chloro-7-methylsulfanyl-quinoline-3-carbaldehyde
• 英文别名: 2-chloro-7-methylsulfanylquinoline-3-carbaldehyde
• CAS: 73568-30-6
• 化学式: C₁₁H₈ClNOS
• mdl: MFCD02049247
• 分子量: 237.71
• InChiKey: AZKPVKLQVQZMHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  55.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2-chloro-7-methylsulfanyl-quinoline-3-carbaldehyde 在 碘 、 sodium 、 potassium carbonate 作用下， 生成
  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
• 作为产物：
  描述：

  3-氨基茴香硫醚 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 生成 2-chloro-7-methylsulfanyl-quinoline-3-carbaldehyde
  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

• A versatile new synthesis of quinolines and related fused pyridines, Part 5. The synthesis of 2-chloroquinoline-3-carbaldehydes
  作者：Otto Meth-Cohn、Bramha Narine、Brian Tarnowski

  DOI：10.1039/p19810001520

  日期：——

  Acetanilides are converted into 2-chloroquinoline-3-carbaldehydes in good yield by the action of Vilsmeier's reagent in phosphoryl chloride solution. The reaction is shown to involve successive conversion of the acetanilide in to an imidoyl chloride and then an N-(α-chlorovinyl)aniline. The latter enamine is diformylated at its β-position and subsequently cyclised to the chloroquinolinecarbaldehyde

  在Vylsmeier试剂在磷酰氯溶液中的作用下，乙酰苯胺以高收率转化为2-氯喹啉-3-甲醛。已表明该反应涉及将乙酰苯胺依次转化为亚氨酰氯，然后转化为N-（α-氯乙烯基）苯胺。后者的烯胺在其β-位被二甲酰化，随后环化成氯喹啉甲醛。可以在几种情况下分离二甲酰化的中间体，并分别用多磷酸环化。
• (1H-tetrazol-5-yl)-2(1H)-quinolinones
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0120483A1

  公开（公告）日：1984-10-03

  (1H-Tetrazol-5-yl)-2(1H)-quinolones useful as antiallergic agents are described herein. The compounds are prepared by the reaction of sodium azide and ammonium chloride with an appropriate 3-cyano-2(1 H)-quinolinone.

  (1H-四唑-5-基)-2(1H)-喹啉酮可用作抗过敏剂，其制备方法是叠氮化钠和氯化铵与适当的 3-氰基-2(1H)-喹啉酮反应。
• Strongly Polarized π-Extended 1,4-Dihydropyrrolo[3,2-<i>b</i>]pyrroles Fused with Tetrazolo[1,5-<i>a</i>]quinolines
  作者：Mohammad B. Teimouri、Irena Deperasińska、Matt Rammo、Marzena Banasiewicz、Charles W. Stark、Łukasz Dobrzycki、Michał K. Cyrański、Aleksander Rebane、Daniel T. Gryko

  DOI：10.1021/acs.joc.3c02916

  日期：2024.4.5

  multicomponent reaction affording 1,4-dihydropyrrolo[3,2-b]pyrroles combined with intramolecular direct arylation enables assembly of these products in just three steps from anilines with overall yields exceeding 30%. The planarized, ladder-type heteroacenes possess up to 14 conjugated rings. These nominally quadrupolar materials exhibit efficient fluorescence with wavelengths spanning most of the visible spectrum

  已经开发出一种由两个吸电子喹啉或四唑并[1,5- a ]喹啉支架组成的1,4-二氢吡咯并[3,2- b ]吡咯的直接途径。提供 1,4-二氢吡咯并[3,2- b ]吡咯的多功能多组分反应与分子内直接芳基化相结合，只需三个步骤即可从苯胺组装这些产物，总产率超过 30%。平面化梯型杂并苯拥有多达 14 个共轭环。这些名义上的四极材料表现出高效的荧光，波长跨越大部分可见光谱，从绿-黄（对于具有联芳基桥的染料）到橙-红色（对于完全融合的系统）。在许多情况下，荧光量子产率大，溶剂化荧光变色效应强，并且即使在结晶状态下也能保持荧光。使用量子化学方法对这些分子结构的电子结构进行分析表明，侧翼杂环的特征和位置决定了HOMO和LUMO的形状及其向N-芳基取代基的延伸，从而影响摩尔吸收系数的值。对双光子吸收 (2PA) 特性的实验研究表明，它发生在 700–800 nm 范围内，明显偏离拉波特宇称选择规则，这可能归因于赫茨伯格-泰勒对振动允许的
• METH-COHN O.; NARINE B.; TARNOWSKI B., TETRAHEDRON LETT., 1979, NO 33, 3111-3114
  作者：METH-COHN O.、 NARINE B.、 TARNOWSKI B.

  DOI：——

  日期：——
• METH-COHN O.; NARINE B.; TARNOWSKI B., J. CHEM. SOC. PERKIN TRANS., 1981, PART 1, NO 5, 1520-1530
  作者：METH-COHN O.、 NARINE B.、 TARNOWSKI B.

  DOI：——

  日期：——