5,7-dimethyl-2-phenylquinolin-4(1H)-one | 1070879-75-2

• 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: 5,7-dimethyl-2-phenylquinolin-4(1H)-one
• 英文别名: 5,7-Dimethyl-2-phenylquinolin-4-ol；5,7-dimethyl-2-phenyl-1H-quinolin-4-one
• CAS: 1070879-75-2
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: LWGDYKNQKDYFPS-UHFFFAOYSA-N

物化性质

• 沸点：
  457.6±33.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,7-dimethyl-2-phenylquinolin-4(1H)-one 在 sodium hydroxide 、 sode de l'acide trichloroisocyanurique 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 3,3,6,8-tetrachloro-2,3-dihydro-2-methoxy-5,7-dimethyl-2-phenylquinolin-4(1H)-one
  参考文献：
  名称：

  Production of 3- benzoyl-2,1-benzisoxazoles,2-phenyl-4H-3,1-benzoxazin-4-ones, and novel quinolinone derivatives from 2-phenylquinolin-4(1H)-ones and sodium dichloroisocyanurate

  摘要：

  A simple synthesis of certain 3-benzoyl-2,1 -benzisoxazoles 6 is accomplished via treatment of the corresponding 2-phenylquinolin-4(1H)-one 1 with sodium dichloroisocyanurate 2 in methanolic aq. alkali; the isomeric 2-phenyl-4H-3,1-benzoxazin-4-one 7 is also a product. Under different conditions the same reactants furnish two new types of quinolinone derivative, viz. 3,3-dichloro-2-phenylquinolin-4(3H)-one 4 and 2-alkoxy-3,3-dichloro-2,3-dihydro-2-phenylquinolin-4(1H)-one 5, as chief products; the former is an intermediate in the synthesis of products 6 and 7. Some of the chemical properties of the dichloro compounds 4 and 5 are described. Mechanistic pathways and proposals to explain the results and observations are presented.

  DOI：

  10.1039/p19930000511
• 作为产物：
  描述：

  在 tetrabutylammonium tetrafluoroborate 、 sodium t-butanolate 作用下， 以 二甲基亚砜 、 叔丁醇 为溶剂， 反应 3.0h， 以57%的产率得到5,7-dimethyl-2-phenylquinolin-4(1H)-one
  参考文献：
  名称：

  电化学分子内氧化 C(sp3)–H/C(sp3)–H 偶联合成 4-喹诺酮类

  摘要：

  在无金属和无外部氧化剂的条件下，开发了一种通过分子内 C(sp 3 )-H/C(sp 3 )-H 交叉偶联合成 4-喹诺酮类药物的有效电化学方法。这种电化学方法提供了一种简单有效的途径来构建有用的 4-喹诺酮衍生物，产率适中至高。

  DOI：

  10.1055/a-1942-7110

文献信息

• From Ketones, Amines, and Carbon Monoxide to 4-Quinolones: Palladium-Catalyzed Oxidative Carbonylation
  作者：Jiwei Wu、Yuchen Zhou、Ting Wu、Yi Zhou、Chien-Wei Chiang、Aiwen Lei

  DOI：10.1021/acs.orglett.7b03337

  日期：2017.12.1

  A novel method of palladium-catalyzed oxidative carbonylation of ketones, amines, and carbon monoxide for the synthesis of 4-quinolones has been developed. This protocol provides a straightforward route to construct useful 4-quinolone derivatives from inexpensive chemicals.

  已开发了钯催化的酮，胺和一氧化碳的羰基氧化羰基化合成4-喹诺酮的新方法。该协议提供了一种直接的途径，可以从廉价的化学品中构建有用的4-喹诺酮衍生物。
• Staskun Baniamin, van Es Theodorus, J. Chem. Soc. Perkin Trans. 1, (1993) N 4, S 511- 516
  作者：Staskun Baniamin, van Es Theodorus

  DOI：——

  日期：——
• Production of 3- benzoyl-2,1-benzisoxazoles,2-phenyl-4H-3,1-benzoxazin-4-ones, and novel quinolinone derivatives from 2-phenylquinolin-4(1H)-ones and sodium dichloroisocyanurate
  作者：Benjamin Staskun、Theodorus van Es

  DOI：10.1039/p19930000511

  日期：——

  A simple synthesis of certain 3-benzoyl-2,1 -benzisoxazoles 6 is accomplished via treatment of the corresponding 2-phenylquinolin-4(1H)-one 1 with sodium dichloroisocyanurate 2 in methanolic aq. alkali; the isomeric 2-phenyl-4H-3,1-benzoxazin-4-one 7 is also a product. Under different conditions the same reactants furnish two new types of quinolinone derivative, viz. 3,3-dichloro-2-phenylquinolin-4(3H)-one 4 and 2-alkoxy-3,3-dichloro-2,3-dihydro-2-phenylquinolin-4(1H)-one 5, as chief products; the former is an intermediate in the synthesis of products 6 and 7. Some of the chemical properties of the dichloro compounds 4 and 5 are described. Mechanistic pathways and proposals to explain the results and observations are presented.
• Electrochemical Intramolecular Oxidative C(sp3)–H/C(sp3)–H Coupling for the Synthesis of 4-Quinolones
  作者：Jiwei Wu、Kejun Jin、Ruiyou Wang、Xingyu Wang、Xiaoxiao Yu、Liangcheng Zhong、Jianguo Liu

  DOI：10.1055/a-1942-7110

  日期：2023.2

  An efficient electrochemical approach for the synthesis of 4-quinolones via intramolecular C(sp3)–H/C(sp3)–H cross-coupling has been developed under metal- and external oxidant-free conditions. This electrochemical approach provides a simple and efficient route to construct useful 4-quinolone derivatives in moderate to good yields.

  在无金属和无外部氧化剂的条件下，开发了一种通过分子内 C(sp 3 )-H/C(sp 3 )-H 交叉偶联合成 4-喹诺酮类药物的有效电化学方法。这种电化学方法提供了一种简单有效的途径来构建有用的 4-喹诺酮衍生物，产率适中至高。