3-phenyl-1H-pyrano[3',4':4,5]imidazo[1,2-a]pyridin-1-one | 1005162-05-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并[1，2-a]吡啶
• 英文名称: 3-phenyl-1H-pyrano[3',4':4,5]imidazo[1,2-a]pyridin-1-one
• 英文别名: 3-phenylpyrano[3',4':4,5]imidazo[1,2-a]pyridinone；4-Phenyl-5-oxa-1,8-diazatricyclo[7.4.0.02,7]trideca-2(7),3,8,10,12-pentaen-6-one；4-phenyl-5-oxa-1,8-diazatricyclo[7.4.0.02,7]trideca-2(7),3,8,10,12-pentaen-6-one
• CAS: 1005162-05-9
• 化学式: C₁₆H₁₀N₂O₂
• 分子量: 262.268
• InChiKey: PQLIMAAJXXKRSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(phenylethynyl)imidazo[1,2-a]pyridine-2-carboxylic acid 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 反应 0.33h， 以90%的产率得到3-phenyl-1H-pyrano[3',4':4,5]imidazo[1,2-a]pyridin-1-one
  参考文献：
  名称：

  6-endo-dig Cyclization of heteroarylesters to alkynes promoted by Lewis acid catalyst in the presence of Brønsted acid

  摘要：

  We report a regiocontrolled 6-endo-dig cyclization of 2-(2-arylethynyl)heteroaryl esters occurred under Bronsted acidic conditions and in the presence of a catalytic amount of Lewis acids such as Cu(OTf)(2), AUCl(3), or (CF3CO2)Ag. A variety of heteroc yclic lactones are readily prepared in excellent yields. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.020

文献信息

• Copper(<scp>i</scp>)-mediated preparation of new pyrano[3′,4′:4,5]imidazo[1,2-a]pyridin-1-one compounds under mild palladium-free conditions
  作者：Zineb Bahlaouan、Mohamed Abarbri、Alain Duchêne、Jérôme Thibonnet、Nicolas Henry、Cécile Enguehard-Gueiffier、Alain Gueiffier

  DOI：10.1039/c0ob00622j

  日期：——

  ylic acid, and terminal alkynes was developed under very mild conditions. This method allows the introduction in one pot of a third ring fused in positions 2 and 3 of the imidazo[1,2-a]pyridine core with reasonable yields and total regioselectivity. This procedure does not require the use of any expensive supplementary additives, and is palladium-free.

  一般有效的Cu（I）介导的C的交叉偶联和杂环化反应3-碘咪唑并[1,2- a ]吡啶-2-羧酸，并且末端炔烃是在非常温和的条件下形成的。该方法允许以合理的收率和总区域选择性在一个锅中引入稠合在咪唑并[1,2- a ]吡啶核的2和3位的第三环。该步骤不需要使用任何昂贵的补充添加剂，并且不含钯。