methyl (E)-6-(benzhydrylideneamino)oxyhex-5-enoate | 1453804-83-5

• 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: methyl (E)-6-(benzhydrylideneamino)oxyhex-5-enoate
• CAS: 1453804-83-5
• 化学式: C₂₀H₂₁NO₃
• 分子量: 323.392
• InChiKey: ULFHDNBYWLLIKT-MHWRWJLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E)-6-(benzhydrylideneamino)oxyhex-5-enoate 以 二氧六环-d8 为溶剂， 反应 0.5h， 以56%的产率得到methyl 5-((diphenylmethylene)amino)-6-oxohexanoate
  参考文献：
  名称：

  Preparation of α-Imino Aldehydes by [1,3]-Rearrangements of O-Alkenyl Oximes

  摘要：

  The synthesis of alpha-imino aldehydes has been achieved through the thermal [1,3]-rearrangement of O-alkenyl benzophenone oximes. A copper. mediated C-O bond coupling between benzophenone oxime and alkenyl boronic acids provides facile access to the required O-alkenyl oximes and a Horner-Wadsworth-Emmons olefination can be applied to the a-imino aldehyde products to give gamma-imino-alpha,beta-unsaturated esters. The scope of the method is described and mechanistic experiments are discussed.

  DOI：

  10.1021/ol402237w
• 作为产物：
  描述：

  在 三乙烯二胺 、 噻吩-2-甲酸亚铜(I) 、 水 、 silver perchlorate 、 sodium sulfate 作用下， 以 乙醚 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 3.25h， 生成 methyl (E)-6-(benzhydrylideneamino)oxyhex-5-enoate
  参考文献：
  名称：

  Preparation of α-Imino Aldehydes by [1,3]-Rearrangements of O-Alkenyl Oximes

  摘要：

  The synthesis of alpha-imino aldehydes has been achieved through the thermal [1,3]-rearrangement of O-alkenyl benzophenone oximes. A copper. mediated C-O bond coupling between benzophenone oxime and alkenyl boronic acids provides facile access to the required O-alkenyl oximes and a Horner-Wadsworth-Emmons olefination can be applied to the a-imino aldehyde products to give gamma-imino-alpha,beta-unsaturated esters. The scope of the method is described and mechanistic experiments are discussed.

  DOI：

  10.1021/ol402237w