1-phenyl-1H,3H,5H-oxazolo[3,4-a]quinolin-3-one | 73731-08-5

• 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-phenyl-1H,3H,5H-oxazolo[3,4-a]quinolin-3-one
• 英文别名: 1-phenyl-5H-oxazolo[3,4-a]quinolin-3-one；1-Phenyl-1,5-dihydro-[1,3]oxazolo[3,4-a]quinolin-3-one
• CAS: 73731-08-5
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: YMGRDEKFMPOYKI-UHFFFAOYSA-N

物化性质

• 沸点：
  511.1±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenyl-1H,3H,5H-oxazolo[3,4-a]quinolin-3-one 在 氨 作用下， 以 甲醇 、 乙醚 、 甲苯 为溶剂， 反应 48.0h， 生成 2-p-tolyl-4a,5-dihydro-1H,4H-cyclopropa[e]imidazo[1,5-a]quinoline-1,3(2H)-dione
  参考文献：
  名称：

  Synthesis of 1,2,7,7a-Tetrahydro-1aH-cyclopropa[b]quinoline-1a-carboxylic Acid Derivatives, Doubly Constrained ACC Derivatives, by a Remarkable Cyclopropanation Process

  摘要：

  Reaction of N-benzoyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid with acetic anhydride resulted in 1H,3H,5H-oxazolo[3,4-a]quinolin-3-one derivative 13. Different cyclopropanation processes were applied to 13, but only diazomethane in the presence of water furnished the hitherto unknown methyl 1,2,7,7a-tetrahydro-1aH-cyclopropa[b]quinoline-la-carboxylate 14, which can be considered as a doubly constrained 1-aminocyclopropane-1-carboxylic acid system. The mechanism of the cyclopropanation was studied in detail. The new ACC ester 14 was transformed into fused tetracyclic hydantoin derivatives, which comprised a new type of heterocyclic system.

  DOI：

  10.1021/jo010993z
• 作为产物：
  描述：

  N-benzoyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid 以 乙酸酐 为溶剂， 反应 1.0h， 以71%的产率得到1-phenyl-1H,3H,5H-oxazolo[3,4-a]quinolin-3-one
  参考文献：
  名称：

  Synthesis of 1,2,7,7a-Tetrahydro-1aH-cyclopropa[b]quinoline-1a-carboxylic Acid Derivatives, Doubly Constrained ACC Derivatives, by a Remarkable Cyclopropanation Process

  摘要：

  Reaction of N-benzoyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid with acetic anhydride resulted in 1H,3H,5H-oxazolo[3,4-a]quinolin-3-one derivative 13. Different cyclopropanation processes were applied to 13, but only diazomethane in the presence of water furnished the hitherto unknown methyl 1,2,7,7a-tetrahydro-1aH-cyclopropa[b]quinoline-la-carboxylate 14, which can be considered as a doubly constrained 1-aminocyclopropane-1-carboxylic acid system. The mechanism of the cyclopropanation was studied in detail. The new ACC ester 14 was transformed into fused tetracyclic hydantoin derivatives, which comprised a new type of heterocyclic system.

  DOI：

  10.1021/jo010993z

文献信息

• Zecchini,G.P.; Paradisi,M.P., Journal of Heterocyclic Chemistry, 1979, vol. 16, p. 1589 - 1597
  作者：Zecchini,G.P.、Paradisi,M.P.

  DOI：——

  日期：——
• Synthesis of 1,2,7,7a-Tetrahydro-1a<i>H</i>-cyclopropa[<i>b</i>]quinoline-1a-carboxylic Acid Derivatives, Doubly Constrained ACC Derivatives, by a Remarkable Cyclopropanation Process
  作者：Zsolt Szakonyi、Ferenc Fülöp、Dirk Tourwé、Norbert De Kimpe

  DOI：10.1021/jo010993z

  日期：2002.4.1

  Reaction of N-benzoyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid with acetic anhydride resulted in 1H,3H,5H-oxazolo[3,4-a]quinolin-3-one derivative 13. Different cyclopropanation processes were applied to 13, but only diazomethane in the presence of water furnished the hitherto unknown methyl 1,2,7,7a-tetrahydro-1aH-cyclopropa[b]quinoline-la-carboxylate 14, which can be considered as a doubly constrained 1-aminocyclopropane-1-carboxylic acid system. The mechanism of the cyclopropanation was studied in detail. The new ACC ester 14 was transformed into fused tetracyclic hydantoin derivatives, which comprised a new type of heterocyclic system.