3,4-dihydro-4-phenylquinolin-2(1H),5,8-triene | 188774-17-6

• 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: 3,4-dihydro-4-phenylquinolin-2(1H),5,8-triene
• 英文别名: 4-phenyl-3,4-dihydro-1H-quinoline-2,5,8-trione
• CAS: 188774-17-6
• 化学式: C₁₅H₁₁NO₃
• 分子量: 253.257
• InChiKey: NJWHUTRJFCYGKM-UHFFFAOYSA-N

物化性质

• 沸点：
  515.0±50.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  63.24
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-4-phenylquinolin-2(1H),5,8-triene 在 氧气 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 7-Methyl-4-phenyl-3,4-dihydro-1H-pyrido[3,2-g]quinoline-2,5,10-trione
  参考文献：
  名称：

  Synthesis and reactivity of Michael adducts of lithiated 2,5-dimethoxy-N-pivaloylanilines and arylidenemalonates

  摘要：

  Michael addition of lithiated 2,5-dimethoxypivaloylaniline to diisopropyl arylidenmaionates, followed by acid cyclization, affords 5,8-dimethoxy-4-aryl-3,4-dihydro-2(1H)quinolinines (5). These compounds are very inert to the 3,4-dehydrogenation, but were easily transformed to 4-aryl-3,4-dihydro-(1H)quinoline-2,5,8-triones (10) which, through Diels-Alder heterocyclization, gave 4-aryl-3,4-dihydro- 1,8-diazaanthracene-2,9,10-triones (16). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00034-3
• 作为产物：
  描述：

  亚苯甲基丙二酸二乙酯 在 盐酸 、 正丁基锂 、 ammonium cerium(IV) nitrate 、 溶剂黄146 作用下， 以 水 、 乙腈 为溶剂， 反应 19.5h， 生成 3,4-dihydro-4-phenylquinolin-2(1H),5,8-triene
  参考文献：
  名称：

  Synthesis and reactivity of Michael adducts of lithiated 2,5-dimethoxy-N-pivaloylanilines and arylidenemalonates

  摘要：

  Michael addition of lithiated 2,5-dimethoxypivaloylaniline to diisopropyl arylidenmaionates, followed by acid cyclization, affords 5,8-dimethoxy-4-aryl-3,4-dihydro-2(1H)quinolinines (5). These compounds are very inert to the 3,4-dehydrogenation, but were easily transformed to 4-aryl-3,4-dihydro-(1H)quinoline-2,5,8-triones (10) which, through Diels-Alder heterocyclization, gave 4-aryl-3,4-dihydro- 1,8-diazaanthracene-2,9,10-triones (16). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00034-3

文献信息

• The synthesis of pyrido(2,3,4-<i>kl</i>)acridine unit of some marine alkaloids
  作者：Turan Ozturk、Alexander McKillop

  DOI：10.1139/v00-119

  日期：2000.9.1

  A simple and convenient synthesis of pyrido(2,3,4-kl)acridine (1), the main skeleton of some marine alkaloids, via cyclization and intramolecular nitrene insertion, is described. The importance of the planarity of the molecule during the nitrene insertion is explained.Key words: pyridoacridine, marine alkaloids, nitrene insertion, quinoline, quinolinone.

  通过环化和分子内亚硝基插入，简单方便地合成了一些海洋生物碱的主要骨架吡啶并(2,3,4-kl)吖啶(1)。解释了分子在亚硝基插入过程中平面性的重要性。关键词：吡啶并吖啶，海洋生物碱，亚硝基插入，喹啉，喹啉酮。