N-[(E)-3,3-dimethylbut-1-enoxy]-1,1-bis(4-methylphenyl)methanimine | 1453804-99-3

• 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: N-[(E)-3,3-dimethylbut-1-enoxy]-1,1-bis(4-methylphenyl)methanimine
• CAS: 1453804-99-3
• 化学式: C₂₁H₂₅NO
• 分子量: 307.436
• InChiKey: AYJOASYFKATXSD-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  1,1-diphenyl-N-[(E)-prop-1-enoxy]methanimine 、 N-[(E)-3,3-dimethylbut-1-enoxy]-1,1-bis(4-methylphenyl)methanimine 以 二氧六环-d8 为溶剂， 反应 3.0h， 以50%的产率得到2-((di-p-tolylmethylene)amino)-3,3-dimethylbutanal
  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：

  2-[(1E)-3,3-二甲基-1-丁烯基]-4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷 在 三乙烯二胺 、 sodium periodate 、 噻吩-2-甲酸亚铜(I) 、 ammonium acetate 、 水 、 silver perchlorate 、 sodium sulfate 作用下， 以 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 3.0h， 生成 N-[(E)-3,3-dimethylbut-1-enoxy]-1,1-bis(4-methylphenyl)methanimine
  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

文献信息

• Preparation of α-Imino Aldehydes by [1,3]-Rearrangements of <i>O</i>-Alkenyl Oximes
  作者：Dimitra Kontokosta、Daniel S. Mueller、Heng-Yen Wang、Laura L. Anderson

  DOI：10.1021/ol402237w

  日期：2013.9.20

  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.