4-氯-3-苯基喹啉 | 6319-32-0

• 物质功能分类: 医药中间体 - 杂环化合物 - 喹啉类化合物
• 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: 4-氯-3-苯基喹啉
• 英文名称: 4-chloro-3-phenylquinoline
• 英文别名: 4-chloro-3-phenyl-quinoline；4-Chlor-3-phenyl-chinolin
• CAS: 6319-32-0
• 化学式: C₁₅H₁₀ClN
• 分子量: 239.704
• InChiKey: XMMDHTGEXKLBFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-氯-3-苯基喹啉 在 甲醇 、 sodium hydroxide 、 sodium methylate 作用下， 生成 1-methyl-3-phenylquinolin-4(1H)-one
  参考文献：
  名称：

  349.亚硝基酰基芳基胺。第五部分。3-乙酰氨基-4-喹诺酮类和-喹诺酮类的亚硝化

  摘要：

  DOI：

  10.1039/jr9510001521
• 作为产物：
  描述：

  3-苯基喹啉-4(1h)-酮 在 三氯氧磷 作用下， 反应 2.0h， 以88%的产率得到4-氯-3-苯基喹啉
  参考文献：
  名称：

  Praveen; Parthasarathy; Kumar, P. Senthil, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 3, p. 373 - 382

  摘要：

  DOI：

文献信息

• Synthesis of 4-Aryl-2-aminopyridine Derivatives and Related Compounds
  作者：Vladimir Pavlovic、Milos Petkovic、Stanimir Popovic、Vladimir Savic

  DOI：10.1080/00397910902898601

  日期：2009.11.5

  Abstract A short, efficient, and high-yielding synthesis of 4-aryl-2-aminopyridine derivatives has been developed. The route employs two palladium-catalyzed processes, the Suzuki reaction and the Buchwald–Hartwig amination, as the key steps. The same approach has been used for preparation of the corresponding quinoline derivatives. In addition, a brief study of biological properties showed the anticancer

  摘要 4-芳基-2-氨基吡啶衍生物的快速、高效、高产合成已被开发。该路线采用两个钯催化过程，铃木反应和 Buchwald-Hartwig 胺化，作为关键步骤。相同的方法已用于制备相应的喹啉衍生物。此外，对生物学特性的简要研究显示了这些化合物的抗癌潜力。
• Synthesis of 2-Phenyl-4-chloroquinolines¹
  作者：Robert C. Elderfield、Walter J. Gensler、Thomas H. Bembry、Chester B. Kremer、James D. Head、Frederick Brody、Roger Frohardt

  DOI：10.1021/ja01211a042

  日期：1946.7
• 634. Some 4-(dialkylaminoalkylamino)-3-phenylquinolines
  作者：W. J. Adams、D. H. Hey

  DOI：10.1039/jr9500003254

  日期：——
• Schofield, Joseph; Smalley, Robert K.; Scopes, David I. C., Journal of Chemical Research, Miniprint, 1987, # 5, p. 1401 - 1426
  作者：Schofield, Joseph、Smalley, Robert K.、Scopes, David I. C.、Patel, Dalpat I.

  DOI：——

  日期：——
• C–H Arylation of Pyridines: High Regioselectivity as a Consequence of the Electronic Character of C–H Bonds and Heteroarene Ring
  作者：Pengfei Guo、Jung Min Joo、Souvik Rakshit、Dalibor Sames

  DOI：10.1021/ja206022p

  日期：2011.10.19

  We report a new catalytic protocol for highly selective C-H arylation of pyridines containing common and synthetically versatile electron-withdrawing substituents (NO(2), CN, F and Cl). The new protocol expands the scope of catalytic azine functionalization as the excellent regioselectivity at the 3- and 4-positions well complements the existing methods for C-H arylation and Ir-catalyzed borylation, as well as classical functionalization of pyridines. Another important feature of the new method is its flexibility to adapt to challenging substrates by a simple modification of the carboxylic acid ligand or the use of silver salts. The regioselectivity can be rationalized on the basis of the key electronic effects (repulsion between the nitrogen lone pair and polarized C-Pd bond at C2-/C6-positions and acidity of the C-H bond) in combination with steric effects (sensitivity to bulky substituents).