tert-butyl 9-oxo-2H-pyrrolo[3,4-b]quinoline-4(9H)-carboxylate | 1421590-63-7

• 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: tert-butyl 9-oxo-2H-pyrrolo[3,4-b]quinoline-4(9H)-carboxylate
• 英文别名: tert-butyl 9-oxo-2H-pyrrolo[3,4-b]quinoline-4-carboxylate
• CAS: 1421590-63-7
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: KDZNLOUJGQXBBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 9-oxo-2H-pyrrolo[3,4-b]quinoline-4(9H)-carboxylate 在 SiO_{2 solid support} 作用下， 反应 0.25h， 以53%的产率得到2-(Aminomethyl)quinoline-3,4-dione
  参考文献：
  名称：

  Convenient Route to 2H-Pyrrolo[3,4-b]quinolin-9(4H)-one Skeleton via TosMIC Reaction

  摘要：

  A practical and versatile method for the synthesis of 2H-pyrrolo[3,4-b]quinolin-9(4H)-one skeleton via tosylmethyl isocyanide (TosMIC) reaction has been developed. Many attempts have been made to reverse the null reactivity of 4-hydroxyquinoline and its N-alkyl derivatives toward TosMIC reactant. For this reason various molecular modifications have been improved for the purpose of obtaining a reactive substrate. tert-Butyl-4-oxoquinoline-1(4H)-carboxylate resulted in the best substrate to provide the desired tricyclic system via facile TosMIC reaction.

  DOI：

  10.1080/00397911.2011.622062
• 作为产物：
  描述：

  1-Boc-4-quinolone 在 sodium hydride 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 16.0h， 生成 tert-butyl 9-oxo-2H-pyrrolo[3,4-b]quinoline-4(9H)-carboxylate
  参考文献：
  名称：

  Convenient Route to 2H-Pyrrolo[3,4-b]quinolin-9(4H)-one Skeleton via TosMIC Reaction

  摘要：

  A practical and versatile method for the synthesis of 2H-pyrrolo[3,4-b]quinolin-9(4H)-one skeleton via tosylmethyl isocyanide (TosMIC) reaction has been developed. Many attempts have been made to reverse the null reactivity of 4-hydroxyquinoline and its N-alkyl derivatives toward TosMIC reactant. For this reason various molecular modifications have been improved for the purpose of obtaining a reactive substrate. tert-Butyl-4-oxoquinoline-1(4H)-carboxylate resulted in the best substrate to provide the desired tricyclic system via facile TosMIC reaction.

  DOI：

  10.1080/00397911.2011.622062

文献信息

• Convenient Route to 2<i>H</i>-Pyrrolo[3,4-<i>b</i>]quinolin-9(4<i>H</i>)-one Skeleton via TosMIC Reaction
  作者：Federica Rosi、Giuliana Cuzzucoli Crucitti、Alberto Iacovo、Gaetano Miele、Luca Pescatori、Roberto Di Santo、Roberta Costi

  DOI：10.1080/00397911.2011.622062

  日期：2013.3.1

  A practical and versatile method for the synthesis of 2H-pyrrolo[3,4-b]quinolin-9(4H)-one skeleton via tosylmethyl isocyanide (TosMIC) reaction has been developed. Many attempts have been made to reverse the null reactivity of 4-hydroxyquinoline and its N-alkyl derivatives toward TosMIC reactant. For this reason various molecular modifications have been improved for the purpose of obtaining a reactive substrate. tert-Butyl-4-oxoquinoline-1(4H)-carboxylate resulted in the best substrate to provide the desired tricyclic system via facile TosMIC reaction.