8-methoxy-4-phenyl-3,4-dihydro-1H-quinolin-2-one | 25893-57-6

• 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: 8-methoxy-4-phenyl-3,4-dihydro-1H-quinolin-2-one
• CAS: 25893-57-6
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: IKSIDYVQIRHIFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(2-methoxyphenyl)-3-phenylacrylamide 在 三氟甲磺酸 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 1.5h， 生成 8-methoxy-4-phenyl-3,4-dihydro-1H-quinolin-2-one
  参考文献：
  名称：

  The triflic acid-mediated cyclisation of N-benzylcinnamanilides

  摘要：

  N-Benzylcinnamanilides cyclise with triflic acid to form 1-benzyl-4-aryl-2,4-dihydro-1H-quinolin-2-ones and 2,5-diaryl-benzazepin-3-ones. The product ratio is determined by the preferred orientation of the amide and by the electronics of the substituents. With ortho-substituted anilides, N-debenzylation also occurs to give 4-aryl-2,4-dihydro-1H-quinoline-2-ones. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.075

文献信息

• Enantioselective cyclocarbonylation of 2-vinylanilines to six-membered ring lactams
  作者：Chune Dong、Howard Alper

  DOI：10.1016/j.tetasy.2003.08.045

  日期：2004.1

  A catalyst system based on Pd(OAC)(2)/(2S,4S)-(-)-4-diphenylphosphino-2-(diphenylphosphinomethyl)pyrrolidine has been found to effect asymmetric cyclocarbonylation of 2-vinylanilines to enantiomerically enriched six-membered ring lactams in excellent yield. The reaction was effected under an atmosphere of CO (500 psi) and H, (100 psi) in methylene chloride for 48 h; the chiral six-membered ring lactams were isolated in up to 98% yield and 84% ee. The stereoselectivity was influenced by the structure of the substrate and the reaction conditions. The enantiopurity of the lactam was further improved by recrystallization with 99% ee obtained in some cases. (C) 2003 Elsevier Ltd. All rights reserved.