6-chloro-2-phenyl-2,3-dihydroquinolin-4(1H)-one | 1133158-36-7

• 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: 6-chloro-2-phenyl-2,3-dihydroquinolin-4(1H)-one
• 英文别名: 6-chloro-2-phenyl-2,3-dihydro-4(1H)-quinolone；6-chloro-2-phenyl-2,3-dihydro-1H-quinolin-4-one
• CAS: 1133158-36-7
• 化学式: C₁₅H₁₂ClNO
• 分子量: 257.719
• InChiKey: LZHPYYPRIUAWJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3-二氢-2-苯基-4(1H)-喹啉 在 (二氯碘)-苯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以74%的产率得到6-chloro-2-phenyl-2,3-dihydroquinolin-4(1H)-one
  参考文献：
  名称：

  Facile Iodine(III)-Mediated Approach for the Regioselective Chlorination of 2-Aryl-2,3-dihydro-4(1H)-quinolones

  摘要：

  Oxidation of 2-aryl-2,3-dihydro-4(1H)-quinolones (1) with 1.5 equivalents of (dichloroiodo)benzene in dichloromethane at room temperature leads to regioselective chlorination, thereby offering an efficient method for the synthesis of new 2-aryl-6-chloro-2,3-dihydro-4(1H)-quinolones (3).

  DOI：

  10.1080/00397910802413865

文献信息

• Mild and Efficient Silver(I) Triflate Catalyzed Synthesis of 2-Aryl-2,3-dihydroquinolin-4(1H)-ones, and Their Antioxidant Activities
  作者：Yong Lee、Rameshwar Pandit、Kavita Sharma

  DOI：10.1055/s-0035-1560322

  日期：——

  Biologically interesting 2-aryl-2,3-dihydroquinolin-4(1H)-ones were synthesized using a mild and efficient one-pot procedure starting from o-aminoacetophenones and aromatic aldehydes in the presence of silver(I) triflate. This synthetic protocol provides rapid access to a variety of 2-aryl-2,3-dihydroquinolin-4(1H)-ones. This technique has several advantages, such as the use of easily available starting materials, the efficiency of the catalyst, a simple operation, and tolerance of a wide range of functionality in the aldehydes. Screening of the synthesized compounds for their antioxidant properties revealed that two compounds (with EC50 = 15.42 M and 15.16 M) exhibit a potent free-radical scavenging ability towards TEAC free radicals compared to the standard, Trolox.
• Facile Iodine(III)-Mediated Approach for the Regioselective Chlorination of 2-Aryl-2,3-dihydro-4(1<i>H</i>)-quinolones
  作者：Deepak Sharma、Pooja Ranjan、Om Prakash

  DOI：10.1080/00397910802413865

  日期：2009.1.28

  Oxidation of 2-aryl-2,3-dihydro-4(1H)-quinolones (1) with 1.5 equivalents of (dichloroiodo)benzene in dichloromethane at room temperature leads to regioselective chlorination, thereby offering an efficient method for the synthesis of new 2-aryl-6-chloro-2,3-dihydro-4(1H)-quinolones (3).