2-苯基喹啉-3-羧酸甲酯 | 1018071-63-0

• 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
• 中文名称: 2-苯基喹啉-3-羧酸甲酯
• 英文名称: methyl 2-phenylquinoline-3-carboxylate
• 英文别名: Methyl 2-phenylquinoline-3-carboxylate
• CAS: 1018071-63-0
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: OKUDVGVDODBCIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  422.6±33.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-苯基喹啉-3-羧酸甲酯 在 盐酸 、 硫酸 、 一水合肼 、 sodium nitrite 作用下， 反应 2.0h， 生成 3-bromo-2-phenylquinoline
  参考文献：
  名称：

  John, Journal fur praktische Chemie (Leipzig 1954), 1931, vol. <2> 131, p. 346,347

  摘要：

  DOI：
• 作为产物：
  描述：

  Methyl 2-[(2-bromoanilino)-phenylmethyl]prop-2-enoate 在 palladium diacetate potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以58%的产率得到2-苯基喹啉-3-羧酸甲酯
  参考文献：
  名称：

  Pd-mediated synthesis of 2-arylquinolines and tetrahydropyridines from modified Baylis–Hillman adducts

  摘要：

  We synthesized 2-arylquinolines and tetrahydropyridines via palladium-mediated Heck type reactions starting from the Baylis-Hillman adducts. 2-Arylquinolines were prepared via the Heck type cyclization followed by concomitant aerobic oxidation. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.12.133

文献信息

• Palladium-Catalyzed Intermolecular Aerobic Annulation of <i>o</i>-Alkenylanilines and Alkynes for Quinoline Synthesis
  作者：Jia Zheng、Zun Li、Liangbin Huang、Wanqing Wu、Jianxiao Li、Huanfeng Jiang

  DOI：10.1021/acs.orglett.6b01008

  日期：2016.8.5

  A new approach to construct 2,3-disubstituted quinolines is described via Pd-catalyzed oxidative cyclization of o-vinylanilines and alkynes with molecular oxygen. This transformation is supposed to undergo intermolecular amination of alkyne, insertion of the olefin, and oxidative cleavage of C–C bond sequence.

  通过Pd催化邻乙烯基苯胺和炔烃与分子氧的氧化环化，描述了一种构建2,3-二取代喹啉的新方法。据认为，这种转变经历了炔烃的分子间胺化，烯烃的插入以及C–C键序列的氧化裂解。
• Palladium-Catalyzed Sequential Formation of CC Bonds: Efficient Assembly of 2-Substituted and 2,3-Disubstituted Quinolines
  作者：Xiaochen Ji、Huawen Huang、Yibiao Li、Huoji Chen、Huanfeng Jiang

  DOI：10.1002/anie.201202412

  日期：2012.7.16

  A series of substituted quinolines was prepared from arylamines, aldehydes, and terminal olefins (see scheme). The palladium‐catalyzed sequential formation of CC bonds proceeds smoothly with both electron‐deficient and electron‐rich olefins. When acrylic acid is used as terminal olefin, decarboxylation occurs to provide 2‐substituted quinolines.

  由芳基胺，醛和末端烯烃制得一系列取代的喹啉（参见方案）。钯催化的CC键的顺序形成与贫电子烯烃和富电子烯烃均能顺利进行。当丙烯酸用作末端烯烃时，会发生脱羧反应，提供2个取代的喹啉。
• FeCl3-promoted formation of C–C bonds: synthesis of substituted quinolines from imines and electron-deficient alkynes
  作者：Yu-feng Li、Zheng-guang Wu、Jie Shi、Yi Pan、Hong-zhong Bu、Hong-fei Ma、Jia-chao Gu、Hao Huang、Yao-zhu Wang、Lin Wu

  DOI：10.1016/j.tet.2014.05.051

  日期：2014.11

  An efficient method for the synthesis of substituted quinolines is described. By FeCl3-promoted C–C bond formation, 2,3-disubstituted and 2,3,4-trisubstituted quinolines were successfully synthesized from the reaction between imines and electron-deficient alkynes in good yields. The reaction can also be performed in a sequential three-component manner by using aromatic amines and aromatic aldehydes

  描述了一种合成取代喹啉的有效方法。通过FeCl 3促进的CC键形成，成功地从亚胺和电子不足的炔烃之间的反应中成功合成了2,3-二取代和2,3,4-三取代的喹啉。该反应还可以通过使用芳族胺和芳族醛代替相应的亚胺以连续的三组分方式进行。
• Copper-Catalyzed Tandem Reaction of Enamino Esters with <i>ortho</i> -Halogenated Aromatic Carbonyls: One-Pot Approach to Functionalized Quinolines
  作者：Fei Peng、Jin Liu、Lili Li、Zhiwei Chen

  DOI：10.1002/ejoc.201701472

  日期：2018.2.7

  tandem reaction was developed for the efficient synthesis of functionalized quinolones. The C–C bond formation and C–N coupling reaction of enamino esters and ortho‐halogenated aromatic carbonyl compounds gave products in moderate to good yields. A successful gram‐scale protocol and synthesis of a thieno[3,2‐b]pyridine derivative show further applications of this approach.

  为了有效合成功能化喹诺酮，开发了铜催化串联反应。烯氨基酯与邻卤代芳族羰基化合物的C–C键形成和C–N偶联反应使产物收率适中至良好。成功的克级规程和噻吩并[3,2- b ]吡啶衍生物的合成表明了该方法的进一步应用。
• Controlled and Efficient Synthesis of Quinoline Derivatives from Morita–Baylis–Hillman Adducts by Palladium-Catalyzed Heck Reaction and Cyclization
  作者：Kodirajan Selvakumar、Kandapalam Lingam、Rama Varma、Veerappan Vijayabaskar

  DOI：10.1055/s-0034-1379938

  日期：——

  An efficient synthesis of 2,3-disubstituted quinoline derivatives from easily accessible (het)aryl-substituted Morita–Baylis–Hillman (MBH) adducts was achieved by an approach involving a palladium-catalyzed Heck reaction and cyclization. This strategy converts the MBH adducts into α-benzyl β-keto ester derivatives that can cyclize into the corresponding quinolines in good yields.

  通过涉及钯催化的 Heck 反应和环化的方法，实现了从易于获得的（杂）芳基取代的 Morita-Baylis-Hillman (MBH) 加合物有效合成 2,3-二取代喹啉衍生物。该策略将 MBH 加合物转化为 α-苄基 β-酮酯衍生物，该衍生物可以高产率环化成相应的喹啉。