(Z)-2-chloro-1-(4-methoxyphenyl)ethanone O-methyl oxime | 183986-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-2-chloro-1-(4-methoxyphenyl)ethanone O-methyl oxime
• 英文别名: (Z)-2-chloro-N-methoxy-1-(4-methoxyphenyl)ethanimine
• CAS: 183986-35-8
• 化学式: C₁₀H₁₂ClNO₂
• 分子量: 213.664
• InChiKey: BARDJPXXMKNVAL-ZRDIBKRKSA-N

物化性质

• 沸点：
  285.8±50.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  (Z)-2-chloro-1-(4-methoxyphenyl)ethanone O-methyl oxime 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 18.0h， 生成 (E,E,E)-1,3-bis-(4-Methoxyphenyl)-2-butene-1,4-dione-bis-(O-methyloxime)
  参考文献：
  名称：

  1,3-Diphenylpropan-1,3-diamines IX. reaction of ?-chlorooxime ethers with ?-lithiobenzylamines

  摘要：

  The carbanions of the benzylamine derivatives 1-4 have been reacted with alpha-chlorooxime ether 5 in order to gel precursors of 1,3-diphenylpropane-1,3-diamines. Isonitrile 1 afforded the expected result, whereas lithiated benzamide 2 underwent oxidative dimerization and transmetallated chlorooxime derivative 5. Isoxazolidine 3 gave the condensation product 21 as a mixture of diastereomers; treatment of imine 4 led to the desired amine-oxime 15 in low yield.

  DOI：

  10.1007/bf00817268
• 作为产物：
  描述：

  甲氧基胺盐酸盐 、 2-氯-4-甲氧基苯乙酮 在 硫酸 作用下， 以 乙醇 为溶剂， 以80%的产率得到(Z)-2-chloro-1-(4-methoxyphenyl)ethanone O-methyl oxime
  参考文献：
  名称：

  钯催化的α-卤代甲基肟醚的Suzuki羰基化反应：向不对称1,3-Oxyiminoketones的区域选择性路线。

  摘要：

  AbstractThe three‐component reaction of α‐halomethyl oxime ethers, boronic acids and carbon monoxide at atmospheric pressure catalyzed by tetrakis(triphenylphosphine)palladium(0) gives efficiently unsymmetrical β‐alkoxyimino carbonyl compounds with total control of the regioselectivity, in high yield and atomic economy. Simple commercially available starting materials are used in this synthetic procedure. The three components assembly takes place preferentially versus the competing direct coupling or other possible side reactions. The mechanism of the transformation was investigated by NMR and intermediate palladium(II) complexes were detected.magnified image

  DOI：

  10.1002/adsc.201400442

文献信息

• Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Halomethyl Oxime Ethers and Site-Selective Cross-Coupling of Dihalo Derivatives
  作者：Bárbara Noverges、Cristian Mollar、Mercedes Medio-Simón、Gregorio Asensio

  DOI：10.1002/adsc.201300444

  日期：2013.8.12

  AbstractThe cross‐coupling reaction of chloro‐ and bromomethyl oxime ethers with a wide range of aryl‐, heteroaryl‐ and vinylboronic acids in the presence of catalytic palladium complexes with different phosphines has been carried out with good yields (60–98%, 40 examples). Regioselective cross‐coupling reactions differentiating between an alkyl or aryl position are achieved from dihalo oxime ethers containing Csp2‐ and Csp3‐halogen bonds using mono‐ or dicoordinated palladium catalysts such as Pd(dba)2/P(o‐tolyl)3 or Pd(PPh3)4. The selective orthogonal functionalization of dihalo oxime ethers is also described. Site‐selective transformations allow the introduction of the biaryl motif into dihalo oxime ethers preserving the highly activated alkyl halide moiety vicinal to the oxime group for further transformations. In this context, Z‐ and E‐oxime ethers could be considered as synthetic equivalents of ketones in palladium‐catalyzed Suzuki reactions.magnified image
• 1,3-Diphenylpropane-1,3-diamines XII [1]. A Novel Approach to Stereodefined Oximes and Oxime Ethers of Monothioketalized 1,3-Diketones and their Conversion to 3-Aminooximes
  作者：Alexander Kaiser、Wolfgang Wiegrebe

  DOI：10.1007/pl00013502

  日期：1998.9

  Mono-O,O- and mono-S,S-ketals of 1,3-diphenylpropane-1,3-diones react with hydroxylamine hydrochloride and O-methylhydroxylamine hydrochloride affording mixtures of (E/Z) isomers which are hard to separate or an even unseparable. Isomerically pure oximes and O-methyloximes, however, are obtained either from 2-lithiated 1,3-dithianes and alpha-halogeno-oximes and alpha-halogeno-oxime ethers, resp., or from lithiated oxime ethers and dithienium salts. Reduction, acetylation, hydrolysis of the ketal increment, and oximation afford 3-amino-oximes which are precursors of 1,3-diphenylpropane-1,3-diamines.