ethyl 6-methylquinoline-2-carboxylate

• 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: ethyl 6-methylquinoline-2-carboxylate
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: BANCPVUAFFRVLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-碘-4-甲基苯胺 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 ethyl 6-methylquinoline-2-carboxylate
  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

• [EN] PYRAZOLE DERIVATIVES USEFUL AS INHIBITORS OF FAAH<br/>[FR] DÉRIVÉS DE PYRAZOLE UTILES COMME INHIBITEURS DE FAAH
  申请人：MERCK & CO INC

  公开号：WO2009151991A1

  公开（公告）日：2009-12-17

  The present invention is directed to certain imidazole derivatives which are useful as inhibitors of Fatty Acid Amide Hydrolase (FAAH). The invention is also concerned with pharmaceutical formulations comprising these compounds as active ingredients and the use of the compounds and their formulations in the treatment of certain disorders, including osteoarthritis, rheumatoid arthritis, diabetic neuropathy, postherpetic neuralgia, skeletomuscular pain, and fibromyalgia, as well as acute pain, migraine, sleep disorder, Alzheimer disease, and Parkinson's disease

  本发明涉及某些咪唑衍生物，其可用作脂肪酰胺水解酶（FAAH）的抑制剂。该发明还涉及包含这些化合物作为活性成分的药物配方，以及这些化合物及其配方在治疗某些疾病中的使用，包括骨关节炎、类风湿性关节炎、糖尿病神经病变、带状疱疹后神经痛、骨骼肌肉疼痛和纤维肌痛，以及急性疼痛、偏头痛、睡眠障碍、阿尔茨海默病和帕金森病。
• Iron-Catalyzed Oxidative Tandem Reactions with TEMPO Oxoammonium Salts: Synthesis of Dihydroquinazolines and Quinolines
  作者：Renate Rohlmann、Tobias Stopka、Heinrich Richter、Olga Garcı́a Mancheño

  DOI：10.1021/jo4007199

  日期：2013.6.21

  formation or C–C bond formation upon homocondensation or reaction with simple olefins, respectively. Cyclization followed by a final oxidation generates these classes of interesting bioactive heterocycles in one synthetic transformation. Additionally, the one-pot multicomponent synthesis of quinolines from anilines, aldehydes, and olefins has also been successfully developed under these mild oxidative conditions

  已经开发了使用TEMPO氧铵盐作为温和，无毒的氧化剂，由N-烷基苯胺直接催化铁催化的二氢喹唑啉和喹啉的发散性串联氧化反应。Fe（OTf）2是形成二氢喹唑啉的首选路易斯酸催化剂，而FeCl 3则可以更好地合成喹啉。这种发散的方法意味着，对于两种合成，N的α-C（sp 3）–H键的直接氧化功能化-烷基苯胺的出现，分别导致它们与均相缩合或与简单烯烃反应时形成C–N键或形成C–C键。环化后再进行最终氧化，可以在一个合成转化中生成这类有趣的生物活性杂环。此外，在这些温和的氧化条件下，还成功地开发了由苯胺，醛和烯烃单锅多组分合成喹啉的方法。
• 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。
• TEMPO Oxoammonium Salt-Mediated Dehydrogenative Povarov/Oxidation Tandem Reaction of N-Alkyl Anilines
  作者：Heinrich Richter、Olga García Mancheño

  DOI：10.1021/ol202552y

  日期：2011.11.18

  The synthesis of a variety of substituted quinolines from N-alkyl anilines by a one-pot dehydrogenative Povarov/oxidation tandem reaction with mono- and 1,2-disubstituted aryl and alkyl olefins was developed. A simple protocol using cheap and benign iron(III)chloride as the Lewis acid catalyst and a TEMPO oxoammonium salt as a nontoxic, mild, efficient oxidant is reported.

  通过单-，1,2-二取代的芳基和烷基烯烃的一锅式脱氢Povarov /氧化串联反应，从N-烷基苯胺合成了多种取代的喹啉。据报道，有一种简单的方法，使用廉价且良性的氯化铁（III）作为路易斯酸催化剂，并使用TEMPO氧铵盐作为无毒，温和，有效的氧化剂。
• Enol Esters:  Versatile Substrates for Mannich-Type Multicomponent Reactions
  作者：Nicolas Isambert、Montse Cruz、María José Arévalo、Elena Gómez、Rodolfo Lavilla

  DOI：10.1021/ol701717z

  日期：2007.10.1

  The interaction of cyclic enol esters with diversely substituted anilines and ethyl glyoxalate yields, under Sc(OTf)3 catalysis, disubstituted N-aryl lactams in a multicomponent reaction. The protocol allows access to the trans stereoisomers after an epimerization of the initial mixture in which the cis isomers predominate. Vinyl acetate yields quinoline derivatives, whereas isopropenyl acetate leads

  在Sc（OTf）3催化下，环烯醇酯与不同取代的苯胺和乙二醛酸乙酯的相互作用产生多组分反应中的双取代N-芳基内酰胺。该方案允许在顺式异构体占优势的初始混合物发生差向异构化后，进入反式立体异构体。乙酸乙烯酯产生喹啉衍生物，而乙酸异丙烯酯导致相应的曼尼希加合物。