2-(benzo[d]oxazol-2-yl)-8-methoxyquinoline | 1268386-92-0

• 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: 2-(benzo[d]oxazol-2-yl)-8-methoxyquinoline
• 英文别名: 8-methoxy-2-(2-benzoxazolyl)quinoline；2-(8-Methoxyquinolin-2-yl)-1,3-benzoxazole；2-(8-methoxyquinolin-2-yl)-1,3-benzoxazole
• CAS: 1268386-92-0
• 化学式: C₁₇H₁₂N₂O₂
• 分子量: 276.294
• InChiKey: BWSPBNQIBSWOPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  48.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  8-methoxyquinoline-2-carbaldehyde O-phenyl oxime 在 氧气 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以85%的产率得到2-(benzo[d]oxazol-2-yl)-8-methoxyquinoline
  参考文献：
  名称：

  Copper(II)-Catalyzed Conversion of Bisaryloxime Ethers to 2-Arylbenzoxazoles via C−H Functionalization/C−N/C−O Bonds Formation

  摘要：

  A copper(II)-catalyzed conversion of bisaryloxime ethers to 2-arylbenzoxazoles has been developed. The reaction involves a cascade C H functionalization and C N/C-O bond formation under oxygen atmosphere.

  DOI：

  10.1021/ol2000809

文献信息

• Base-Promoted Cross-Dehydrogenative Coupling of Quinoline <i>N</i>-Oxides with 1,3-Azoles
  作者：Xiaopei Chen、Xiuling Cui、Fangfang Yang、Yangjie Wu

  DOI：10.1021/acs.orglett.5b00330

  日期：2015.3.20

  An efficient cross-dehydrogenative coupling of quinoline N-oxides and 1,3-azoles has been developed under external oxidant and metal free conditions. The desired products were isolated in good to excellent yields for 26 examples. This methodology provides a practical pathway to biheteroaryls and features high practicality, high efficiency, and environmental friendliness.
• Copper-Mediated Synthesis of Substituted 2-Aryl-<i>N</i>-benzylbenzimidazoles and 2-Arylbenzoxazoles via C–H Functionalization/C–N/C–O Bond Formation
  作者：Murali Mohan Guru、Md Ashif Ali、Tharmalingam Punniyamurthy

  DOI：10.1021/jo2005632

  日期：2011.7.1

  An efficient method for the transformation of N-benzyl bisarylhydrazones and bisaryloxime ethers to functionalized 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles is described. The protocol involves a copper(II)-mediated cascade C-H functionalization/C-N/C-O bond formation under neutral conditions. Substrates having either electron-donating or -withdrawing substituents undergo the cyclization to afford the target heterocycles at moderate temperature.
• Copper(II)-Catalyzed Conversion of Bisaryloxime Ethers to 2-Arylbenzoxazoles via C−H Functionalization/C−N/C−O Bonds Formation
  作者：Murali Mohan Guru、Md Ashif Ali、Tharmalingam Punniyamurthy

  DOI：10.1021/ol2000809

  日期：2011.3.4

  A copper(II)-catalyzed conversion of bisaryloxime ethers to 2-arylbenzoxazoles has been developed. The reaction involves a cascade C H functionalization and C N/C-O bond formation under oxygen atmosphere.