N-[(1SR,2RS)-2-nitro-1,3-diphenylpropyl]prop-2-en-1-amine

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-[(1SR,2RS)-2-nitro-1,3-diphenylpropyl]prop-2-en-1-amine
• 英文别名: (1R,2S)-2-nitro-1,3-diphenyl-N-prop-2-enylpropan-1-amine
• 化学式: C₁₈H₂₀N₂O₂
• 分子量: 296.369
• InChiKey: IBYDGIHMDCEEQP-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-N-烯丙基-1-苯基甲亚胺 、 β-硝基苯乙烯 在 三乙基硼氢化锂 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 5.17h， 生成 N-[(1SR,2SR)-2-nitro-1,3-diphenylpropyl]prop-2-en-1-amine 、 N-[(1SR,2RS)-2-nitro-1,3-diphenylpropyl]prop-2-en-1-amine
  参考文献：
  名称：

  Diastereoselective Reductive Nitro-Mannich Reactions

  摘要：

  A range of nitroalkenes 1 and imines 3 derived from alkyl, aryl, and heteroaryl aldehydes underwent a tandem 1,4-hydride addition nitro-Mannich reaction to afford anti-rich beta-nitroamines 4. The crude anti-beta-nitroamines 4 could be converted to the corresponding anti-beta-nitroacetamides 5 (33 examples) to allow purification in good yield from the parent nitroalkenes (60-87%), and with a high diastereomeric ratio (90:10 to mostly >95:5). A representative selection of anti-beta-nitroacetamides 5 (five examples) were reduced to vicinal diamines 7 with zinc provided differentially protected vicinal diamines 7 in good yield (80-91%). hydrochloride; concomitant acyl migration

  DOI：

  10.1021/jo300535h

文献信息

• Diastereoselective Reductive Nitro-Mannich Reactions
  作者：James C. Anderson、Alexander J. Blake、Paul J. Koovits、Gregory J. Stepney

  DOI：10.1021/jo300535h

  日期：2012.5.18

  A range of nitroalkenes 1 and imines 3 derived from alkyl, aryl, and heteroaryl aldehydes underwent a tandem 1,4-hydride addition nitro-Mannich reaction to afford anti-rich beta-nitroamines 4. The crude anti-beta-nitroamines 4 could be converted to the corresponding anti-beta-nitroacetamides 5 (33 examples) to allow purification in good yield from the parent nitroalkenes (60-87%), and with a high diastereomeric ratio (90:10 to mostly >95:5). A representative selection of anti-beta-nitroacetamides 5 (five examples) were reduced to vicinal diamines 7 with zinc provided differentially protected vicinal diamines 7 in good yield (80-91%). hydrochloride; concomitant acyl migration