1-m-tolyl-1,2-dihydro-2-quinolone | 117741-11-4

• 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: 1-m-tolyl-1,2-dihydro-2-quinolone
• 英文别名: 1-(m-tolyl)quinolin-2(1H)-one；1-(3-Methylphenyl)quinolin-2-one
• CAS: 117741-11-4
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: XUCIMLCPIUQTGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (2E)-N-(3-methylphenyl)-3-phenylprop-2-enamide 在 bis[3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridyl]phenyl]iridium(1+); 2-(2-pyridyl)pyridine; hexafluorophosphate 、 tributylmethylammonium dibutyl phosphate 作用下， 以 1,2-二氯乙烷 为溶剂， 以54%的产率得到1-m-tolyl-1,2-dihydro-2-quinolone
  参考文献：
  名称：

  Visible-Light-Photocatalyzed Synthesis of Phenanthridinones and Quinolinones via Direct Oxidative C–H Amidation

  摘要：

  A straightforward synthetic strategy to construct biologically relevant phenanthridinones and quinolinones was developed via visible-light-promoted direct oxidative C-H amidation. In this photocatalytic system, amidyl radicals can be generated by homolysis of the N-H bond of simple amide precursors via single-electron transfer under blue LED illumination, which leads to oxidative intramolecular C-H amidation. Moreover, an efficient synthetic strategy using a photocascade enabled facile assembly of quinolinone structures through a catalytic sequence involving triplet energy (E-T) transfer based E/Z olefin isomerization and subsequent photocatalytic generation of amidyl radical intermediates.

  DOI：

  10.1021/acs.orglett.7b03600

文献信息

• WAWZONEK, STANLEY;TRUONG, THIEN VAN, J. HETEROCYCL. CHEM., 25,(1988) N 2, C. 381-382
  作者：WAWZONEK, STANLEY、TRUONG, THIEN VAN

  DOI：——

  日期：——
• Wawzonek, Stanley; Truong, Thien Van, Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 381 - 382
  作者：Wawzonek, Stanley、Truong, Thien Van

  DOI：——

  日期：——
• Visible-Light-Photocatalyzed Synthesis of Phenanthridinones and Quinolinones via Direct Oxidative C–H Amidation
  作者：Yonghoon Moon、Eunyoung Jang、Soyeon Choi、Sungwoo Hong

  DOI：10.1021/acs.orglett.7b03600

  日期：2018.1.5

  A straightforward synthetic strategy to construct biologically relevant phenanthridinones and quinolinones was developed via visible-light-promoted direct oxidative C-H amidation. In this photocatalytic system, amidyl radicals can be generated by homolysis of the N-H bond of simple amide precursors via single-electron transfer under blue LED illumination, which leads to oxidative intramolecular C-H amidation. Moreover, an efficient synthetic strategy using a photocascade enabled facile assembly of quinolinone structures through a catalytic sequence involving triplet energy (E-T) transfer based E/Z olefin isomerization and subsequent photocatalytic generation of amidyl radical intermediates.