1-phenyl-N-[(1R)-1-phenyl-2-phenylmethoxyethyl]methanimine oxide | 1224883-18-4

• 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-phenyl-N-[(1R)-1-phenyl-2-phenylmethoxyethyl]methanimine oxide
• CAS: 1224883-18-4
• 化学式: C₂₂H₂₁NO₂
• 分子量: 331.414
• InChiKey: RCVJLZCROUDKMD-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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-phenyl-N-[(1R)-1-phenyl-2-phenylmethoxyethyl]methanimine oxide 、 1-(叔丁基二甲基硅氧基)-1-甲氧基乙烯 在 zinc trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以55%的产率得到methyl 3-[[tert-butyl(dimethyl)silyl]oxy-[(1R)-1-phenyl-2-phenylmethoxyethyl]amino]-3-phenylpropanoate
  参考文献：
  名称：

  Experimental and theoretical studies on Mannich-type reactions of chiral non-racemic N-(benzyloxyethyl) nitrones

  摘要：

  The nucleophilic addition of both silyl ketene acetals and lithium enolates derived from methyl acetate to chiral non-racemic N-(benzyloxyethyl)nitrones has been studied both experimentally and theoretically. Aromatic nitrones showed lower reactivity that aliphatic nitrones and the addition of the silyl ketene acetal led to lower selectivities than the addition of the corresponding lithium enolate. Whereas low selectivity was obtained for the addition of the silyl ketene acetal, only one diastereomer could be detected in all cases for the addition of lithium enolate to aliphatic nitrones. The synthetic utility of the two chiral auxiliaries employed lies in the preparation of enantiomeric compounds. DFT theoretical calculations confirmed the stepwise mechanism for the addition of silyl ketene acetals to nitrones and are in good agreement with the observed experimental results. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.12.004

文献信息

• Experimental and theoretical studies on Mannich-type reactions of chiral non-racemic N-(benzyloxyethyl) nitrones
  作者：Alba Diez-Martinez、Tomas Tejero、Pedro Merino

  DOI：10.1016/j.tetasy.2010.12.004

  日期：2010.12

  The nucleophilic addition of both silyl ketene acetals and lithium enolates derived from methyl acetate to chiral non-racemic N-(benzyloxyethyl)nitrones has been studied both experimentally and theoretically. Aromatic nitrones showed lower reactivity that aliphatic nitrones and the addition of the silyl ketene acetal led to lower selectivities than the addition of the corresponding lithium enolate. Whereas low selectivity was obtained for the addition of the silyl ketene acetal, only one diastereomer could be detected in all cases for the addition of lithium enolate to aliphatic nitrones. The synthetic utility of the two chiral auxiliaries employed lies in the preparation of enantiomeric compounds. DFT theoretical calculations confirmed the stepwise mechanism for the addition of silyl ketene acetals to nitrones and are in good agreement with the observed experimental results. (C) 2010 Elsevier Ltd. All rights reserved.