(E)-1-phenyl-2-p-tolylethanone O-methyloxime | 113694-72-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-1-phenyl-2-p-tolylethanone O-methyloxime
• 英文别名: (E)-N-methoxy-2-(4-methylphenyl)-1-phenylethanimine
• CAS: 113694-72-7
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: OAYYONKMYCRDEW-WUKNDPDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  (E)-1-phenyl-2-p-tolylethanone O-methyloxime 、 硼烷 以64%的产率得到
  参考文献：
  名称：

  SAKITO, YOJI;YONEYOSHI, YUKIO;SUZUKAMO, GOHFU, TETRAHEDRON LETT., 29,(1988) N 2, 223-224

  摘要：

  DOI：
• 作为产物：
  描述：

  alpha-氯乙酰苯 在 四(三苯基膦)钯 、 硫酸 、 cesium fluoride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.0h， 生成 (E)-1-phenyl-2-p-tolylethanone O-methyloxime
  参考文献：
  名称：

  钯催化的α-卤代甲基肟醚的铃木-宫浦交叉偶联和二卤代衍生物的位点选择性交叉偶联

  摘要：

  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

  DOI：

  10.1002/adsc.201300444

文献信息

• SAKITO, YOJI;YONEYOSHI, YUKIO;SUZUKAMO, GOHFU, TETRAHEDRON LETT., 29,(1988) N 2, 223-224
  作者：SAKITO, YOJI、YONEYOSHI, YUKIO、SUZUKAMO, GOHFU

  DOI：——

  日期：——
• SAKITO, JODZI;SUDZUKAMO, TAKEHO;JONEHDA, YUKIO
  作者：SAKITO, JODZI、SUDZUKAMO, TAKEHO、JONEHDA, YUKIO

  DOI：——

  日期：——
• 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