1-(4-chlorophenyl)-N-(2-methoxyphenyl)methanimine oxide | 958433-57-3

• 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: 1-(4-chlorophenyl)-N-(2-methoxyphenyl)methanimine oxide
• CAS: 958433-57-3
• 化学式: C₁₄H₁₂ClNO₂
• 分子量: 261.708
• InChiKey: SXYGMXMPALDEAP-YBEGLDIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-N-(2-methoxyphenyl)methanimine oxide 、 (4-methoxybenzoyl)trimethylsilane 在 (R,R)-TADDOL-phosphite 、 lithium hexamethyldisilazane 作用下， 以 various solvent(s) 为溶剂， 反应 0.08h， 以93%的产率得到(R)-2-(4-chlorophenyl)-1-(4-methoxyphenyl)-2-(N-(2-methoxyphenyl)-N-trimethylsilyloxy)aminoethanone
  参考文献：
  名称：

  Enantioselective Metallophosphite-Catalyzed C-Acylation of Nitrones

  摘要：

  Metallophosphites derived from tartaric acid catalyze the enantioselective addition of acyl silanes to nitrones. The product alpha N-silyloxyamino ketones are obtained in moderate to good yields (36-94%) with excellent enantioselectivity (er >= 95:5). The nitrone oxygen is essential in facilitating the silyl transfer that is required for catalyst turnover. This represents, to the best of our knowledge, the first example of C-acylation of nitrones and the most highly enantioselective catalytic addition of an acyl anion equivalent to an azomethine electrophile. The N-O bond of the product may be reductively cleaved under mild conditions to provide N- aryl alpha-amino ketones with negligible loss of enantiopurity.

  DOI：

  10.1021/ja076095n

文献信息

• Enantioselective Metallophosphite-Catalyzed C-Acylation of Nitrones
  作者：Mary R. Garrett、James C. Tarr、Jeffrey S. Johnson

  DOI：10.1021/ja076095n

  日期：2007.10.1

  Metallophosphites derived from tartaric acid catalyze the enantioselective addition of acyl silanes to nitrones. The product alpha N-silyloxyamino ketones are obtained in moderate to good yields (36-94%) with excellent enantioselectivity (er >= 95:5). The nitrone oxygen is essential in facilitating the silyl transfer that is required for catalyst turnover. This represents, to the best of our knowledge, the first example of C-acylation of nitrones and the most highly enantioselective catalytic addition of an acyl anion equivalent to an azomethine electrophile. The N-O bond of the product may be reductively cleaved under mild conditions to provide N- aryl alpha-amino ketones with negligible loss of enantiopurity.