4-methoxybenzaldehyde O-4-chlorophenyl oxime | 1166839-38-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-methoxybenzaldehyde O-4-chlorophenyl oxime
• 英文别名: N-(4-chlorophenoxy)-1-(4-methoxyphenyl)methanimine
• CAS: 1166839-38-8
• 化学式: C₁₄H₁₂ClNO₂
• 分子量: 261.708
• InChiKey: XYALAMDBFZZLOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  30.82
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-methoxybenzaldehyde O-4-chlorophenyl oxime 在 氧气 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以84%的产率得到5-氯-2-(4-甲氧基苯基)-1,3-苯并恶唑
  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
• 作为产物：
  描述：

  4-氯苯硼酸 在 吡啶 、 溶剂黄146 、 copper(I) bromide 、 肼 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 60.5h， 生成 4-methoxybenzaldehyde O-4-chlorophenyl oxime
  参考文献：
  名称：

  Copper-Mediated Synthesis of Substituted 2-Aryl-N-benzylbenzimidazoles and 2-Arylbenzoxazoles via C–H Functionalization/C–N/C–O Bond Formation

  摘要：

  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.

  DOI：

  10.1021/jo2005632

文献信息

• Copper(II) Acetate–Mediated Cross-Coupling of Phenylboronic Acids with Aryloximes: Synthesis of O-Aryloximes
  作者：Xing-Hua Feng、Guo-Zhen Zhang、Cheng-Qun Chen、Ming-Yu Yang、Xiao-Yun Xu、Guo-Sheng Huang

  DOI：10.1080/00397910802590910

  日期：2009.4.22

  A novel method for the synthesis of O-aryloxime is described. It consisted of the coupling reaction between phenylboronic acids and aryloximes in the presence of catalytic quantities of copper(II) acetate. This reaction takes place in the presence of pyridine under a mild condition (DCE, Rt, 24-36h) with moderate yield. It represents a good alternative to known methods for O-aryloxime synthesis.