N-[(4-methoxyphenyl)methyl]-2-methyl-2-nitro-1-phenylpropan-1-amine | 219915-89-6

• 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-[(4-methoxyphenyl)methyl]-2-methyl-2-nitro-1-phenylpropan-1-amine
• CAS: 219915-89-6
• 化学式: C₁₈H₂₂N₂O₃
• 分子量: 314.384
• InChiKey: BZGGRCQGLXXGFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(4-methoxyphenyl)methyl]-2-methyl-2-nitro-1-phenylpropan-1-amine 在 samarium diiodide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 N¹-(4-Methoxy-benzyl)-2-methyl-1-phenyl-propane-1,2-diamine
  参考文献：
  名称：

  The Nitro-Mannich Reaction and Its Application to the Stereoselective Synthesis of 1,2-Diamines

  摘要：

  The addition of alkyl nitronate anions to PMB imines, derived from benzaldehyde or straight-chain carbaldehydes, in the presence of a Bronsted acid, proceeds in greater than 90% yield with up to 10:1 diastereoselection favoring the anti isomer. The mechanism of this addition reaction is intriguing and is under investigation. The moderately unstable p-nitro amines can be reduced with samarium diiodide and the PMB group removed with CAN, in good overall yields, to give sensitive 1,2-diamines without erosion of diastereoselectivity. This protocol represents a new, stereoselective synthesis of certain 1,2-diamines.

  DOI：

  10.1021/jo981700d
• 作为产物：
  描述：

  2-硝基丙烷 、 N-(4-methoxybenzyl)benzaldimine 在 正丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 N-[(4-methoxyphenyl)methyl]-2-methyl-2-nitro-1-phenylpropan-1-amine
  参考文献：
  名称：

  The Nitro-Mannich Reaction and Its Application to the Stereoselective Synthesis of 1,2-Diamines

  摘要：

  The addition of alkyl nitronate anions to PMB imines, derived from benzaldehyde or straight-chain carbaldehydes, in the presence of a Bronsted acid, proceeds in greater than 90% yield with up to 10:1 diastereoselection favoring the anti isomer. The mechanism of this addition reaction is intriguing and is under investigation. The moderately unstable p-nitro amines can be reduced with samarium diiodide and the PMB group removed with CAN, in good overall yields, to give sensitive 1,2-diamines without erosion of diastereoselectivity. This protocol represents a new, stereoselective synthesis of certain 1,2-diamines.

  DOI：

  10.1021/jo981700d