methyl 6-methyl-2-phenylquinoline-3-carboxylate | 1018071-70-9

• 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: methyl 6-methyl-2-phenylquinoline-3-carboxylate
• 英文别名: Methyl 6-methyl-2-phenylquinoline-3-carboxylate
• CAS: 1018071-70-9
• 化学式: C₁₈H₁₅NO₂
• 分子量: 277.323
• InChiKey: UWTYYUBGUHVJSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  Methyl 2-[(2-bromo-4-methylanilino)-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 1.0h， 以60%的产率得到methyl 6-methyl-2-phenylquinoline-3-carboxylate
  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

• 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。
• Microwave-assisted, regioselective one-pot synthesis of quinolines and bis-quinolines catalyzed by Bi(III) immobilized on triazine dendrimer stabilized magnetic nanoparticles
  作者：Beheshteh Asadi、Amir Landarani-Isfahani、Iraj Mohammadpoor-Baltork、Shahram Tangestaninejad、Majid Moghadam、Valiollah Mirkhani、Hadi Amiri Rudbari

  DOI：10.1016/j.tetlet.2016.11.102

  日期：2017.1

  Fe3O4-TDSN-Bi(III) was utilized as an efficient and reusable catalyst for the regioselective one-pot synthesis of quinoline derivatives from arylamines, arylaldehydes and methyl propiolate under microwave irradiation and solvent-free conditions. Also, bis-quinolines were obtained in high yields from dialdehydes or diamines. Atom-economy, high to excellent yields, easy work-up, as well as simple catalyst

  Fe 3 O 4 -TDSN-Bi（III）被用作有效和可重复使用的催化剂，用于在微波辐射和无溶剂条件下从芳基胺，芳基醛和丙炔酸甲酯区域选择性地一锅合成喹啉衍生物。同样，从二醛或二胺以高收率获得双喹啉。原子经济，高至优异的收率，易于后处理以及简单的催化剂回收和可重复使用性是此程序的关键特征。
• Divergent Synthesis of Functionalized Quinolines from Aniline and Two Distinct Amino Acids
  作者：Jia-Chen Xiang、Zi-Xuan Wang、Yan Cheng、Shi-Qing Xia、Miao Wang、Bo-Cheng Tang、Yan-Dong Wu、An-Xin Wu

  DOI：10.1021/acs.joc.7b01501

  日期：2017.9.1

  A practicable quinoline synthesis from aniline and two amino acids was developed for generating a wide range of quinolines with high efficiency and diversity. Thus, it facilitated the creations of pharmaceutical derivatives, photochemical active compounds, and challenging scaffolds. The concept of using two amino acids as heterocyclic precursors has been raised for the first time. Mechanistic studies

  开发了一种由苯胺和两个氨基酸合成可行的喹啉，以高效和多样性地产生各种喹啉。因此，它促进了药物衍生物，光化学活性化合物和具有挑战性的支架的产生。首次提出了使用两个氨基酸作为杂环前体的概念。机理研究表明，I 2可以使新的C–N和C–C键过程脱羧，氧化脱氨和选择性重建。