2-phenyl-2,6-dihydropyrimido[2,1-a]isoindol-4(3H)-one | 1166376-05-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-phenyl-2,6-dihydropyrimido[2,1-a]isoindol-4(3H)-one
• 英文别名: 2-phenyl-2,3-dihydropyrimido[2,1-a]isoindol-4(6H)-one；2-phenyl-3,6-dihydro-2H-pyrimido[2,1-a]isoindol-4-one
• CAS: 1166376-05-1
• 化学式: C₁₇H₁₄N₂O
• 分子量: 262.311
• InChiKey: YXKCPDAHWJMOPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(2-cyanobenzyl)cinnamamide 在 三氟甲磺酸三甲基硅酯 、 三乙胺 、 水 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到2-phenyl-2,6-dihydropyrimido[2,1-a]isoindol-4(3H)-one
  参考文献：
  名称：

  Intramolecular Formal [4 + 2] Cycloaddition of Nitriles with Amides Triggered by TMSOTf/Et₃N: Highly Efficient Construction of Pyrrolo[1,2-a]pyrimidin-4(6H)-ones

  摘要：

  By treatment with TMSOTf/Et3N, N-(2-cyanoarylmethyl)-substituted acrylamides or beta-ketoamides underwent N-addition cascades under mild conditions to afford the corresponding pyrrolo[1,2-a]pyrimidin-4(6H)-ones as the formal [4 + 2] cycloaddition products in high yields.

  DOI：

  10.1021/jo900907h

文献信息

• Synthesis of Tetracyclic Quinazolinones Using a Visible-Light-Promoted Radical Cascade Approach
  作者：Yue-Yue Han、Heng Jiang、Ruzhi Wang、Shouyun Yu

  DOI：10.1021/acs.joc.6b00869

  日期：2016.8.19

  A practical approach for the synthesis of tetracyclic pyrroloquinazolines using photoredox strategy has been developed. The visible-light-promoted intramolecular single-electron-transfer (SET) process between photocatalyst and N-(2-iodobenzyl)-N-acylcyanamides is considered to be involved in this transformation. Targeted pyrroloquinazoline derivatives (15 examples) are presented in good isolated yields

  已经开发出一种利用光氧化还原策略合成四环吡咯并喹唑啉的实用方法。光催化剂和N-（2-碘苄基）-N-酰基氰酰胺之间的可见光促进的分子内单电子转移（SET）过程被认为参与了这种转化。靶向吡咯并喹唑啉衍生物（15个实例）以良好的分离收率（30％-88％）提供。
• Intramolecular Formal [4 + 2] Cycloaddition of Nitriles with Amides Triggered by TMSOTf/Et₃N: Highly Efficient Construction of Pyrrolo[1,2-<i>a</i>]pyrimidin-4(6<i>H</i>)-ones
  作者：Feng Liu、Chaozhong Li

  DOI：10.1021/jo900907h

  日期：2009.8.7

  By treatment with TMSOTf/Et3N, N-(2-cyanoarylmethyl)-substituted acrylamides or beta-ketoamides underwent N-addition cascades under mild conditions to afford the corresponding pyrrolo[1,2-a]pyrimidin-4(6H)-ones as the formal [4 + 2] cycloaddition products in high yields.