tert-butyl 2-methyl-4-phenylquinoline-3-carboxylate | 1197206-03-3

• 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: tert-butyl 2-methyl-4-phenylquinoline-3-carboxylate
• 英文别名: tert-butyl-2-methyl-4-phenylquinolin-3-carboxylate；Tert-butyl 2-methyl-4-phenyl-quinoline-3-carboxylate
• CAS: 1197206-03-3
• 化学式: C₂₁H₂₁NO₂
• 分子量: 319.403
• InChiKey: LOKGFJGMQWSHPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  乙酰乙酸叔丁酯 、 2-氨基二苯甲酮 在 poly(vinylalcohol)/Fe(NO₃)3 nanofiber mats 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以90%的产率得到tert-butyl 2-methyl-4-phenylquinoline-3-carboxylate
  参考文献：
  名称：

  PVA / Fe（NO 3）3纳米纤维垫：一种高效，多相和可循环利用的催化剂，可通过弗里德兰德环法合成喹啉†

  摘要：

  发现PVA / Fe（NO 3）3纳米纤维毡是一种异质可循环利用的催化剂，可用于2-氨基芳基酮与羰基化合物和β-酮酯的Friedländer缩合反应中喹啉衍生物的高效合成。该新型催化体系可被回收并重复使用至少5次，而不会损失任何催化活性。

  DOI：

  10.1039/c4ra07643e

文献信息

• Friedländer annulation: scope and limitations of metal salt Lewis acid catalysts in selectivity control for the synthesis of functionalised quinolines
  作者：Babita Tanwar、Dinesh Kumar、Asim Kumar、Md. Imam Ansari、Mohammad Mohsin Qadri、Maulikkumar D. Vaja、Madhulika Singh、Asit K. Chakraborti

  DOI：10.1039/c5nj02010g

  日期：——

  products during the reaction involving 2-aminobenzophenone and ethyl acetoacetate. Among a pool of metal halides, tetrafluoroborates, perchlorates, and triflates used as catalysts, In(OTf)3 emerged as the most effective catalyst for the selective/exclusive formation of the Friedländer product. The generality of the In(OTf)3-catalysed Friedländer reaction was demonstrated by the reaction of differently substituted

  检查了金属盐路易斯酸催化剂的范围和局限性，以控制在涉及2-氨基二苯甲酮和乙酰乙酸乙酯的反应过程中弗里德兰德和非​​弗里德兰德产品形成的选择性。在用作催化剂的一系列金属卤化物，四氟硼酸盐，高氯酸盐和三氟甲磺酸盐中，In（OTf）3成为选择性/排他地形成弗里德兰德产品的最有效催化剂。In（OTf）3催化的Friedländer反应的普遍性通过不同取代的2-氨基芳基酮与各种含有活性亚甲基的羰基化合物（例如，，无溶剂条件下的β-酮酸酯，环状/无环β-二酮，环状/酰基酮和芳基/杂芳基甲基酮），以75-92％的收率提供所需的喹啉。
• A New and Efficient Procedure for Friedländer Synthesis of Quinolines in Low Melting Tartaric Acid-Urea Mixtures
  作者：Fei-Ping Ma、Gui-Tian Cheng、Zhi-Guo He、Zhan-Hui Zhang

  DOI：10.1071/ch12025

  日期：——

  A general, efficient and green method for the synthesis of quinoline derivatives via the Friedländer heteroannulation reaction of 2-aminoaryl ketones and α-methylene ketones has been developed, employing low melting mixtures of L-(+)-tartaric acid and urea derivatives as an inexpensive, non-toxic, easily biodegradable reaction medium. The melt acts as both the reaction medium and catalyst, furnishing quinolines in high to excellent yields.

  通过 2-氨基芳基酮和α-亚甲基酮的 Friedländer 异annulation 反应合成喹啉衍生物的通用、高效和绿色方法已经开发出来，该方法采用 L-(+)-酒石酸和脲衍生物的低熔融混合物作为廉价、无毒、易生物降解的反应介质。这种熔体既是反应介质，又是催化剂，能以高产率甚至极高产率生成喹啉类化合物。
• Sulfonic Acid Functionalized Ionic Liquid in Combinatorial Approach, a Recyclable and Water Tolerant-Acidic Catalyst for One-Pot Friedlander Quinoline Synthesis
  作者：Jafar Akbari、Akbar Heydari、Hamid Reza Kalhor、Sirus Azizian Kohan

  DOI：10.1021/cc9001313

  日期：2010.1.11

  SO3H-functionalized ionic liquid was successfully applied as a water tolerant-acidic catalyst for the one-pot domino approach quinoline synthesis in aqueous medium. Various types of quinolines from 2-aminoaryl ketones and β-ketoesters/ketones were prepared in 85−98% yields using the catalytic system of SO3H-functionalized ionic liquid/H2O. The ionic liquids was synthesized in a combinatorial fashion

  成功地将SO 3 H-官能化的离子液体用作耐水酸性催化剂，用于在水性介质中一锅多米诺法喹啉合成。使用SO 3 H官能化的离子液体/ H 2催化体系，由2-氨基芳基酮和β-酮​​酸酯/酮制备了各种类型的喹啉，产率为85-98％O.离子液体以组合方式合成。可以通过过滤方便地从反应混合物中分离出喹啉产物，表明整个过程在水中进行，这是绿色化学的例证。更重要的是，该催化剂可以容易地循环使用五次而不会损失太多活性。本文报道的催化体系具有均相和非均相催化剂的优点。
• Design, development of new synthetic methodology, and biological evaluation of substituted quinolines as new anti-tubercular leads
  作者：Babita Tanwar、Asim Kumar、Perumal Yogeeswari、Dharmarajan Sriram、Asit K. Chakraborti

  DOI：10.1016/j.bmcl.2016.10.082

  日期：2016.12

  Two series of quinoline-based compounds were designed, synthesised and evaluated for anti-tubercular activity against Mycobacterium tuberculosis H(37)Rv (ATCC 27294 strain). A new method for Friedlander quinoline synthesis has been developed in water under the catalytic influence of the Bronsted acid surfactant DBSA. Among the forty-two compounds tested for anti-TB activity, twenty-three compounds exhibited significant activity against the growth of M. tuberculosis (MIC 0.02-6.25 mu g/mL). In particular, the compounds 3b and 3c displayed excellent anti-TB activity with MIC values of 0.2 and 0.39 mu g/mL, respectively, and are more potent than the standard drugs E, Cfx and Z that are clinically used to treat TB. The cytotoxicity of the compounds with MIC <= 6.25 mu g/mL was evaluated against Human Embryonic Kidney 293T cell lines and all of the active compounds were found to be nontoxic (<50% inhibition). The results suggest that the synthesised substituted quinolines are promising leads for development of new drug to treat TB. (C) 2016 Elsevier Ltd. All rights reserved.
• CuO Nanoparticles as an Efficient and Reusable Catalyst for the One-pot Friedlander Quinoline Synthesis
  作者：Jafar Mohammad Nezhad、Jafar Akbari、Akbar Heydari、Behrooz Alirezapour

  DOI：10.5012/bkcs.2011.32.11.3853

  日期：2011.11.20