dimethyl 4-methylquinoline-2,3-dicarboxylate | 10037-31-7

• 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: dimethyl 4-methylquinoline-2,3-dicarboxylate
• 英文别名: 4-methyl-quinoline-2,3-dicarboxylic acid dimethyl ester；4-Methyl-2,3-dicarbomethoxychinolin；Dimethyl 4-methyl-2,3-quinolinedicarboxylate
• CAS: 10037-31-7
• 化学式: C₁₄H₁₃NO₄
• 分子量: 259.262
• InChiKey: DDGYJSFQHGMAKZ-UHFFFAOYSA-N

物化性质

• 熔点：
  97.5-99 °C(Solv: benzene (71-43-2); hexane (110-54-3))
• 沸点：
  358.7±37.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-乙酰苯胺 以 乙腈 为溶剂， 反应 40.0h， 生成 dimethyl 4-methylquinoline-2,3-dicarboxylate
  参考文献：
  名称：

  基于光炸重排的功能化喹啉和苯并[ c ] [2,7]萘啶的合成

  摘要：

  已经开发了一种用于合成官能化喹啉和四氢萘吡啶的有效的一锅法。对位取代的苯胺的光-弗里斯重排得到不同取代的邻氨基酮，其与炔属迈克尔受体如乙炔基二羧酸二甲酯（DMAD）原位反应，得到6，4-二取代的喹啉2，3-二羧酸酯。从衍生自β-丙氨酸的苯胺开始，也可以组装萘啶核。

  DOI：

  10.1021/jo201316k

文献信息

• Synthesis of polysubstituted quinolines via copper(ii)-catalyzed annulation of 2-aminoaryl ketones with alkynoates
  作者：Avik Kumar Bagdi、Sougata Santra、Matiur Rahman、Adinath Majee、Alakananda Hajra

  DOI：10.1039/c3ra45576a

  日期：——

  Copper triflate catalyzed annulation of 2-aminoaryl ketones with internal alkynes has been developed for the synthesis of polysubstituted quinolines in high yields under solvent-free conditions. Phenyl propiolic acid afforded the 3-unsubstituted quinolines via decarboxylation. The protocol is compatible with various internal alkynes and is expected to find wide applications due to its operational simplicity.

  在无溶剂条件下，已开发出铜三氟甲烷磺酸盐催化的2-氨基芳基酮与内烯炔的环化反应，合成高产率的多取代喹啉。苯丙炔酸通过脱羧反应得到3-未取代喹啉。该方法适用于多种内烯炔，因其操作简单，预计将在广泛应用中发挥作用。
• An efficient synthesis of 2,3,4-trisubstituted quinolines through alkynylation-cyclization at ambient temperature
  作者：Dipti R. Patil、Sonali M. Salunkhe、Madhukar B. Deshmukh、Prashant V. Anbhule

  DOI：10.1002/jhet.715

  日期：2011.11

  A series of 2,3,4‐trisubstituted quinoline derivatives have been synthesized by reactions between 2‐aminoaryl ketones and dialkyl acetylenedicarboxylate. The synthetic pathway allows for the direct construction of said quinoline derivatives in pyridine/ethanol at ambient temperature through a zwitterion intermediate. J. Heterocyclic Chem., (2011)

  通过2-氨基芳基酮与乙酰二羧酸二烷基酯的反应合成了一系列的2,3,4-三取代的喹啉衍生物。合成途径允许在环境温度下通过两性离子中间体在吡啶/乙醇中直接构建所述喹啉衍生物。J.杂环化​​学。（2011）
• An Improved Protocol for the Synthesis of Quinoline-2,3-dicarboxylates under Neutral Conditions<i>via</i>Biomimetic Approach
  作者：Bandaru Madhav、Sabbavarapu Narayana Murthy、Kakulapati Rama Rao、Yadavalli Venkata Durga Nageswar

  DOI：10.1002/hlca.200900254

  日期：2010.2

  A mild and efficient protocol for synthesis of quinoline derivatives in aqueous medium under neutral conditions is described. The reaction proceeded smoothly in H2O catalyzed by supramolecular catalyst β‐CD. By this protocol, various quinoline derivatives were synthesized in excellent yields.

  描述了在中性条件下在水性介质中合成喹啉衍生物的温和而有效的方案。该反应在超分子催化剂β -CD催化的H 2 O中顺利进行。通过该方案，以优异的产率合成了各种喹啉衍生物。
• Recyclable nano copper oxide catalyzed synthesis of quinoline-2,3-dicarboxylates under ligand free conditions
  作者：Avudoddi Venkanna、Kokkirala Swapna、Pallapothula Venkateswar Rao

  DOI：10.1039/c3ra47212d

  日期：——

  An efficient protocol was developed for the recyclable nano CuO powder catalyzed synthesis of quinoline derivatives from acetylenedicarboxylates and 2-aminocarbonyl compounds using acetonitrile as solvent at 40 °C in air. A variety of quinoline derivatives were synthesized in good yields with good chemoselectivity in the presence of a catalytic amount of CuO nano powder under ligand/additive free conditions. The catalyst is air-stable, inexpensive and recyclable up to four cycles.

  以乙腈为溶剂，在 40 °C空气中以可回收的纳米 CuO 粉末催化合成乙炔二羧酸盐和 2-氨基羰基化合物的喹啉衍生物。在无配体/添加剂的条件下，在催化量的纳米 CuO 粉末存在下合成了多种喹啉衍生物，产率高，化学选择性好。该催化剂在空气中稳定，价格低廉，可循环使用四次。
• Regioselective intramolecular annulations of ambident β-enamino esters: A diversity-oriented synthesis of nitrogen-containing privileged molecules
  作者：Srinivasarao Yaragorla、Abhishek Pareek

  DOI：10.1016/j.tetlet.2018.01.064

  日期：2018.3

  intramolecular annulation of β-enamino esters is described under solvent-free, calcium-catalysis. 2-aminoaryl ketones and alkyl propiolates undergone a [4+2] annulation to yield substituted quinolines; with an excess of alkyl propiolates, benzodiazepines were formed via a [4+2+1] annulation. We also described a one-pot, 3-component synthesis of quinoline derivatives via a [4+2+2] annulation. Interestingly

  在无溶剂的钙催化下描述了多样性导向的区域选择性β-烯氨基酯的分子内环化反应。对2-氨基芳基酮和丙酸烷基酯进行[4 + 2]环化，生成取代的喹啉；与过量的丙酸烷基酯一起，通过[4 + 2 + 1]环化形成苯并二氮杂。我们还描述了通过[4 + 2 + 2]环化法一锅，三组分合成喹啉衍生物。有趣的是，2-氨基芳基酮会发生自缩合[4 + 4]，生成二苯并重氮电影。