O-phenyl benzaldoxime | 33581-42-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O-phenyl benzaldoxime
• 英文别名: N-phenoxy-1-phenylmethanimine
• CAS: 33581-42-9
• 化学式: C₁₃H₁₁NO
• 分子量: 197.236
• InChiKey: DVMZBNAFEMOUBT-UHFFFAOYSA-N

物化性质

• 熔点：
  51 °C
• 沸点：
  303.2±25.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  O-phenyl benzaldoxime 在 氧气 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以80%的产率得到2-苯基苯并恶唑
  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：

  苯甲醛苯腙 在 copper(II) bis(trifluoromethanesulfonate) 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 33.5h， 生成 O-phenyl benzaldoxime
  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

• Synthesis of Complex Phenols Enabled by a Rationally Designed Hydroxide Surrogate
  作者：Patrick S. Fier、Kevin M. Maloney

  DOI：10.1002/anie.201700244

  日期：2017.4.10

  The conversion of aryl halides to phenols under mild reaction conditions is a longstanding and formidable challenge in organic chemistry. Herein, we report the rational design of a broadly applicable Pd‐catalyzed method to prepare phenols with benzaldehyde oxime as a hydroxide surrogate. These reactions occur under mildly basic conditions and enable the late‐stage hydroxylation of several functionally‐dense

  在温和的反应条件下，芳基卤化物向苯酚的转化是有机化学领域一项长期而艰巨的挑战。本文中，我们报告了广泛适用的Pd催化方法的合理设计，该方法可使用苯甲醛肟作为氢氧化物替代物来制备苯酚。这些反应在温和的碱性条件下发生，可以使几种功能密集的药物样芳基卤化物发生后期羟基化反应。
• O-Aryloxime Ethers from the Copper(II)-Mediated Cross-Coupling of Oximes and Phenylboronic Acids
  作者：Adam Meyer、Abdelselam Ali、Kellie Tuck

  DOI：10.1055/s-0028-1088199

  日期：2009.4

  A direct approach to O-aryloxime ethers by means of the first copper-mediated cross-coupling of aromatic oximes and phenylboronic acids is reported. The O-arylation of acetophenone oximes with phenylboronic acids typically furnished O-aryloxime ethers in good to moderate yields.

  报道了一种通过首次铜介导的芳香氧肟与苯硼酸的交叉偶联直接合成O-芳氧肟醚的方法。用苯硼酸对乙酰苯氧肟进行O-芳基化通常能够在良好到中等的产率下生成O-芳氧肟醚。
• Cesium Carbonate Promoted Direct Arylation of Hydroxylamines and Oximes with Diaryliodonium Salts
  作者：Yang Yang、Xunshen Wu、Jianwei Han、Song Mao、Xiaofei Qian、Limin Wang

  DOI：10.1002/ejoc.201402920

  日期：2014.11

  A transition-metal-free approach for the arylation of hydroxylamines and oximes with diaryliodonium salts was developed. The reaction proceeded smoothly at room temperature in the presence of cesium carbonate. As a result, a wide range of N- and O-arylated hydroxylamines were synthesized in good to excellent yields (45-98%).

  开发了一种不含过渡金属的方法，用于羟胺和肟与二芳基碘盐的芳基化。在碳酸铯存在下，反应在室温下顺利进行。结果，合成了多种 N- 和 O- 芳基化羟胺，产率良好至极好 (45-98%)。
• Facile and Metal-Free Synthesis of Phenols from Benzaldoxime and Diaryliodonium Salts
  作者：Yongsheng Zhou

  DOI：10.3184/174751917x15064232103119

  日期：2017.10

  A metal-free, base-promoted facile synthesis of phenol derivatives utilising diaryliodonium salts as the aryl source and benzaldoxime as the hydroxide surrogate has been developed. The reaction is fast and shows good substrate compatibility, giving the corresponding products in good to excellent yields. A gram-scale synthesis of phenols utilising this protocol has also been achieved.

  利用二芳基碘鎓盐作为芳基源和苯甲醛肟作为氢氧化物替代物，开发了一种无金属、碱促进的苯酚衍生物的简便合成。反应速度快，底物相容性好，相应的产物收率良好。还实现了利用该协议对酚类进行克级合成。
• 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。