(Z)-2-chloro-1-phenylethanone O-methyl oxime | 77561-95-6

• 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: (Z)-2-chloro-1-phenylethanone O-methyl oxime
• 英文别名: (Z)-2-chloro-1-phenylethanone O-methyloxime；(Z)-2-chloro-N-methoxy-1-phenylethanimine
• CAS: 77561-95-6
• 化学式: C₉H₁₀ClNO
• 分子量: 183.637
• InChiKey: QCHJQTHCAGCHOX-PKNBQFBNSA-N

物化性质

• 沸点：
  243.2±42.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  (Z)-2-chloro-1-phenylethanone O-methyl oxime 在 一氧化碳 、 palladium diacetate 、 cesium fluoride 、 1,4-双(二苯基膦)丁烷 、 苯硼酸 作用下， 以 四氢呋喃 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 20.0h， 以6%的产率得到(E)-acetophenone O-methyloxime
  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
• 作为产物：
  描述：

  甲氧基胺盐酸盐 、 alpha-氯乙酰苯 在 硫酸 作用下， 以 乙醇 为溶剂， 以80%的产率得到(Z)-2-chloro-1-phenylethanone 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
• STETTER, J.;BUECHEL, K. -H.;REINECKE, P.;BRANDES, W.;FROHBERGER, P. -E.
  作者：STETTER, J.、BUECHEL, K. -H.、REINECKE, P.、BRANDES, W.、FROHBERGER, P. -E.

  DOI：——

  日期：——
• Palladium-Catalyzed Suzuki Carbonylative Reaction of α-Halomethyl Oxime Ethers: A Regioselective Route to Unsymmetrical 1,3-Oxyiminoketones
  作者：Bárbara Noverges、Mercedes Medio-Simón、Gregorio Asensio

  DOI：10.1002/adsc.201400442

  日期：2014.11.24

  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