4-methoxybenzaldehyde O-phenyl oxime | 519175-49-6

• 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-phenyl oxime
• 英文别名: 1-(4-methoxyphenyl)-N-phenoxymethanimine
• CAS: 519175-49-6
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: JRMHBZHENZWWCW-UHFFFAOYSA-N

物化性质

• 沸点：
  341.9±44.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  17.0
• 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-phenyl oxime 在 氧气 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 反应 3.5h， 以85%的产率得到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：

  N-phenoxyphthalimide 在 溶剂黄146 、 肼 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 12.5h， 生成 4-methoxybenzaldehyde O-phenyl 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

• Comparison of the kinetics of aldehyde sensing by covalent bond formation with hydrazines and hydroxylamines
  作者：Blair K. Troudt、John W. Vue、Philippe Bühlmann

  DOI：10.1016/j.tet.2022.132852

  日期：2022.7

  avoiding use of either aldehyde or probe in a large excess. Hydrazone formation was found to be on average 71 times faster than oxime formation. The rate constants for the reaction of aromatic aldehydes with the phenylhydrazine follow largely the trend predicted by Hammett substituent constants, with the notable exception of the hydrogen bond forming 2-hydroxybenzaldehyde. Unlike in studies with water as

  用于检测醛的分析技术通常涉及与肼或羟胺衍生物反应，分别导致形成腙或肟。虽然有各种使用任何一种衍生化试剂的例子，但只有很少的报告有数据适合回答两种类型的探针中的哪一种可以更快和更有选择性地检测醛。针对这个问题，这项工作使用1 H NMR 光谱来研究芳香族和脂肪族醛与两种衍生化探针苯肼或O的反应动力学-苯基羟胺，在四氢呋喃中和在过量的酸催化剂存在下。开发了一种拟合程序来确定这些二级反应的速率常数，同时避免使用大量过量的醛或探针。发现腙形成平均比肟形成快 71 倍。芳香醛与苯肼反应的速率常数在很大程度上遵循 Hammett 取代基常数预测的趋势，但形成氢键的 2-羟基苯甲醛除外。与以水为溶剂的研究不同，没有发现脂肪醛比芳香醛反应更快。
• 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.
• Polymer-supported copper complex for the direct synthesis of O-aryloxime ethers via cross-coupling of oximes and arylboronic acids
  作者：Liang Wang、Chengyan Huang、Chun Cai

  DOI：10.1016/j.catcom.2009.12.012

  日期：2010.2

  L-proline functionalized chloroacetylated polystyrene supported copper (II) complex was prepared and found to be effective for the cross-coupling reaction between aromatic oximes and arylboronic acids under mild conditions. Only catalytic amount of catalyst was required and no deoximation occurred. The catalyst could be recovered by simple filtration and reused several times without significant loss of activity. (C) 2009 Elsevier B.V. All rights reserved.
• 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.