(E)-benzaldehyde O-(1-phenylprop-2-yn-1-yl) oxime | 1388624-46-1

• 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: (E)-benzaldehyde O-(1-phenylprop-2-yn-1-yl) oxime
• 英文别名: benzaldehyde O-(1-phenylprop-2-yn-1-yl)oxime
• CAS: 1388624-46-1
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: LOWRNEOFORVKBL-GHRIWEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  21.59
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  对甲苯磺酰叠氮 、 (E)-benzaldehyde O-(1-phenylprop-2-yn-1-yl) oxime 在 copper(I) bromide dimethylsulfide complex 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以60%的产率得到(E)-N-((E)-1-(4-methylphenylsulfonamido)-3-phenylallylidene)benzamide
  参考文献：
  名称：

  Copper-Catalyzed Cascade Transformation of O-Propargylic Oximes with Sulfonyl Azides to α,β-Unsaturated N-Acylamidines

  摘要：

  Copper catalyzed cascade transformation of O-propargylic oximes and sulfonyl azides were carried out to efficiently afford alpha,beta-unsaturated N-acylamidines. The reaction involved the intramolecular attack of the oxime group to the ketenimine morety that was generated in situ, followed by the cleavage of the N-O bond.

  DOI：

  10.1021/ol502541w
• 作为产物：
  描述：

  2-((1-phenylprop-2-yn-1-yl)oxy)isoindoline-1,3-dione 在 一水合肼 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (E)-benzaldehyde O-(1-phenylprop-2-yn-1-yl) oxime
  参考文献：
  名称：

  Copper-Catalyzed Skeletal Rearrangement of O-Propargylic Aryloximes into Four-Membered Cyclic Nitrones - Chirality Transfer and Mechanistic Insight

  摘要：

  Copper-catalyzed skeletal rearrangement of O-propargylic aryloximes (E)-1 were carried out to afford the corresponding four-membered cyclic nitrones 2 in good to excellent yields. The optimal reactions conditions of the highly regioselective reactions involved the use of [CuCl(cod)](2) in acetonitrile at 70 degrees C. In the case of (Z)-1, however, the reaction proceeded in the absence of the copper catalysts to afford the identical compound 2 in good yields. Furthermore, the reactions were also carried out using chiral substrates (R)-1 in the presence of Cu catalysts to afford (R)-2 with good levels of chirality transfer.

  DOI：

  10.1055/s-0031-1290819