3a-methyl-5-m-tolyl-3,3a-dihydropyrrolo[1,2-a]quinolin-1(2H)-one | 1189050-88-1

• 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: 3a-methyl-5-m-tolyl-3,3a-dihydropyrrolo[1,2-a]quinolin-1(2H)-one
• 英文别名: 3a-Methyl-5-(3-methylphenyl)-2,3-dihydropyrrolo[1,2-a]quinolin-1-one
• CAS: 1189050-88-1
• 化学式: C₂₀H₁₉NO
• 分子量: 289.377
• InChiKey: SZVSITGTBLZXJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  3-甲基苯乙炔 、 N-phenylpent-4-ynamide 在 silver hexafluoroantimonate 、 gold(III) bromide 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以66%的产率得到3a-methyl-5-m-tolyl-3,3a-dihydropyrrolo[1,2-a]quinolin-1(2H)-one
  参考文献：
  名称：

  Gold-Catalyzed One-Pot Cascade Construction of Highly Functionalized Pyrrolo[1,2-a]quinolin-1(2H)-ones

  摘要：

  An efficient protocol was developed for the synthesis of fused heterocyclic multiring compounds pyrrolo[1,2-a]quinolin-1(2H)-ones via a AuBr3/AgSbF6-catalvzed cascade transformation. Significantly, the strategy affords a straightforward and efficient approach to construction of tricyclic lactam molecular architectures in which two new C-C bonds and one new C-N bond are formed in a one-pot synthetic operation from simple starting materials. Moreover, a broad spectrum of substrates can participate in the process effectively to produce the desired products in good yields and with excellent regio- and chemoselectivities.

  DOI：

  10.1021/jo901418m

文献信息

• Gold-Catalyzed One-Pot Cascade Construction of Highly Functionalized Pyrrolo[1,2-<i>a</i>]quinolin-1(2<i>H</i>)-ones
  作者：Yu Zhou、Enguang Feng、Guannan Liu、Deju Ye、Jian Li、Hualiang Jiang、Hong Liu

  DOI：10.1021/jo901418m

  日期：2009.10.2

  An efficient protocol was developed for the synthesis of fused heterocyclic multiring compounds pyrrolo[1,2-a]quinolin-1(2H)-ones via a AuBr3/AgSbF6-catalvzed cascade transformation. Significantly, the strategy affords a straightforward and efficient approach to construction of tricyclic lactam molecular architectures in which two new C-C bonds and one new C-N bond are formed in a one-pot synthetic operation from simple starting materials. Moreover, a broad spectrum of substrates can participate in the process effectively to produce the desired products in good yields and with excellent regio- and chemoselectivities.