喹啉-2-羧酸-(N-甲基苯胺) | 101444-29-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 喹啉-2-羧酸-(N-甲基苯胺)
• 英文名称: N-methyl-N-phenyl-2-quinolinecarboxamide
• 英文别名: N-Methyl-chinaldinanilid；quinoline-2-carboxylic acid-(N-methyl-anilide)；Chinolin-2-carbonsaeure-(N-methyl-anilid)；N-methyl-N-phenylquinoline-2-carboxamide
• CAS: 101444-29-5
• 化学式: C₁₇H₁₄N₂O
• 分子量: 262.311
• InChiKey: YWKGLOQLXDEZJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  喹啉-2-羧酸-(N-甲基苯胺) 在 potassium phosphate 、 nickel dichloride 、 1,3-双(2,6-二异丙基苯基)氯化咪唑鎓 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以92%的产率得到N-methyl-N-phenylquinolin-2-amine
  参考文献：
  名称：

  使用镍催化的脱羰胺化反应，通过CO挤出分子内重组片段偶联，由酰胺合成of。

  摘要：

  首次建立了由酰胺催化合成synthesis的方法。新开发的CO挤出重组工艺利用了廉价的镍（II）催化剂，并可以高效地提供相应的s。分子内片段偶联显示出优异的化学选择性，从容易获得的酰胺开始，并提供了有价值的alternative合成方案。

  DOI：

  10.1002/chem.201702867
• 作为产物：
  描述：

  喹醛酰氯 、 N-甲基苯胺 在 二氯甲烷 、 三乙胺 作用下， 生成 喹啉-2-羧酸-(N-甲基苯胺)
  参考文献：
  名称：

  Studies with Quinolines. I. Synthesis of Quinaldic Acid and Some of Its Amide Derivatives¹

  摘要：

  DOI：

  10.1021/jo01093a016

文献信息

• Heteroaryl hydroxamic acid derivatives and their use in the treatment, amelioration or prevention of a viral disease
  申请人：F. HOFFMANN-LA ROCHE LTD

  公开号：US20130102600A1

  公开（公告）日：2013-04-25

  The present invention relates to a compound having the general formula I, optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, prodrug, tautomer, racemate, enantiomer, or diastereomer or mixture thereof, which is useful in treating, ameliorating or preventing a viral disease. Furthermore, specific combination therapies are disclosed.

  本发明涉及一种具有通式I的化合物，可选地以药物可接受的盐、溶剂化物、多晶型、前药、互变异构体、外消旋体、对映体、非对映体或其混合物的形式，该化合物在治疗、改善或预防病毒性疾病方面有用。此外，还公开了特定的组合疗法。
• Conversion of amides to esters by the nickel-catalysed activation of amide C–N bonds
  作者：Liana Hie、Noah F. Fine Nathel、Tejas K. Shah、Emma L. Baker、Xin Hong、Yun-Fang Yang、Peng Liu、K. N. Houk、Neil K. Garg

  DOI：10.1038/nature14615

  日期：2015.8

  Although enzymes are able to cleave amide bonds in nature, it is difficult to selectively break the carbon–nitrogen bond of an amide using synthetic chemistry; now the activation and cleavage of these bonds using nickel catalysts is used to convert amides to esters. Although enzymes are able to cleave amide bonds in nature, it is difficult to selectively break the carbon–nitrogen bond of an amide using synthetic chemistry. In this paper the authors demonstrate that amide C–N bonds can be activated and cleaved using nickel catalysts. They used this methodology to convert amides to esters, which is a challenging and underdeveloped transformation. Amides are common functional groups that have been studied for more than a century1. They are the key building blocks of proteins and are present in a broad range of other natural and synthetic compounds. Amides are known to be poor electrophiles, which is typically attributed to the resonance stability of the amide bond1,2. Although amides can readily be cleaved by enzymes such as proteases3, it is difficult to selectively break the carbon–nitrogen bond of an amide using synthetic chemistry. Here we demonstrate that amide carbon–nitrogen bonds can be activated and cleaved using nickel catalysts. We use this methodology to convert amides to esters, which is a challenging and underdeveloped transformation. The reaction methodology proceeds under exceptionally mild reaction conditions, and avoids the use of a large excess of an alcohol nucleophile. Density functional theory calculations provide insight into the thermodynamics and catalytic cycle of the amide-to-ester transformation. Our results provide a way to harness amide functional groups as synthetic building blocks and are expected to lead to the further use of amides in the construction of carbon–heteroatom or carbon–carbon bonds using non-precious-metal catalysis.

  尽管酶能够在自然界中断裂酰胺键，但利用合成化学选择性地打破酰胺的碳—氮键却很困难；现在，使用镍催化剂激活和断裂这些键被用于将酰胺转化为酯。本文作者证明，酰胺C—N键可以使用镍催化剂激活和断裂。他们利用这种方法将酰胺转化为酯，这是一种具有挑战性且发展不足的转化。酰胺是一类常见的官能团，一个多世纪以来一直被研究。它们是蛋白质的关键构建模块，存在于广泛的天然和合成化合物中。酰胺被认为是一种差的亲电试剂，这通常归因于酰胺键的共振稳定性。尽管酶如蛋白酶可以轻易地断裂酰胺，但利用合成化学选择性地打破酰胺的碳—氮键却很困难。在这里，我们证明酰胺碳—氮键可以使用镍催化剂激活和断裂。我们利用这种方法将酰胺转化为酯，这是一种具有挑战性且发展不足的转化。反应方法在极其温和的反应条件下进行，并避免了使用大量过量的醇亲核试剂。密度泛函理论计算为酰胺到酯转化的热力学和催化循环提供了见解。我们的结果为利用酰胺官能团作为合成构建块提供了一种方法，并有望进一步在非贵金属催化的碳—杂原子或碳—碳键构建中使用酰胺。
• Nickel-Catalyzed Conversion of Amides to Carboxylic Acids
  作者：Rachel R. Knapp、Ana S. Bulger、Neil K. Garg

  DOI：10.1021/acs.orglett.0c00885

  日期：2020.4.3

  We report the conversion of amides to carboxylic acids using nonprecious metal catalysis. The methodology strategically employs a nickel-catalyzed esterification using 2-(trimethylsilyl)ethanol, followed by a fluoride-mediated deprotection in a single-pot operation. This approach circumvents catalyst poisoning observed in attempts to directly hydrolyze amides using nickel catalysis. The selectivity

  我们报告了使用非贵金属催化将酰胺转化为羧酸。该方法策略性地采用镍催化的 2-(三甲基甲硅烷基)乙醇酯化反应，然后在单锅操作中进行氟化物介导的脱保护。这种方法避免了在尝试使用镍催化直接水解酰胺时观察到的催化剂中毒。通过竞争实验和复杂的缬氨酸底物的净水解显示了这种转化的选择性和温和性。该策略解决了该领域中使用过渡金属催化的 CN 键活化从酰胺中获得官能团的限制，并且应该证明在合成应用中是有用的。
• Copper-catalyzed efficient direct amidation of 2-methylquinolines with amines
  作者：Hao Xie、Yunfeng Liao、Shuqing Chen、Ya Chen、Guo-Jun Deng

  DOI：10.1039/c5ob00915d

  日期：——

  A copper catalyzed efficient procedure for quinoline-2-carboxamides formation via direct amidation of 2-methylquinolines under oxygen is described.

  一种铜催化的高效程序，通过在氧气下直接对2-甲基喹啉进行酰胺化，形成喹啉-2-甲酰胺。
• Studies with Quinolines. I. Synthesis of Quinaldic Acid and Some of Its Amide Derivatives¹
  作者：JEFFERSON W. DAVIS

  DOI：10.1021/jo01093a016

  日期：1959.11