(S,S)-<2-(tert-butyldimethylsilyloxy)-1-phenylethyl>-(2-methoxy-1-methyl-1-phenylethyl)-amine | 222733-19-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S,S)-<2-(tert-butyldimethylsilyloxy)-1-phenylethyl>-(2-methoxy-1-methyl-1-phenylethyl)-amine
• 英文别名: (2S)-N-[(1S)-2-[tert-butyl(dimethyl)silyl]oxy-1-phenylethyl]-1-methoxy-2-phenylpropan-2-amine
• CAS: 222733-19-9
• 化学式: C₂₄H₃₇NO₂Si
• 分子量: 399.649
• InChiKey: XAEWPXKIIGGFMZ-ISKFKSNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S,S)-<2-(tert-butyldimethylsilyloxy)-1-phenylethyl>-(2-methoxy-1-methyl-1-phenylethyl)-amine 在 lead(IV) acetate 、 盐酸 、 乙醇 、 SCX column 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 生成 (S)-2-methylphenylglycinol
  参考文献：
  名称：

  Highly Diastereoselective Addition of Grignard Reagents to Aliphatic, Enolizable N-Alkylketimines and 2,2-Disubstituted 1,3-Oxazolidines. Asymmetric Synthesis of the Antidepressant Cericlamine

  摘要：

  Grignard reagents were added to 2,2-disubstituted 1,3-oxazolidines and enolizable ketimines prepared from hydroxyacetone and phenylglycinol derivatives, with high to excellent diastereoselectivity, to yield 2,2-disubstituted 1,2-amino alcohol derivatives. Lewis acids had considerable influence on the yield and diastereoselectivity of the addition. This method was applied to the first asymmetric synthesis of the 5-HT reuptake inhibitor Cericlamine.

  DOI：

  10.1021/jo982222+
• 作为产物：
  描述：

  (S)-2-(tert-butyldimethylsilyloxy)-1-phenylethylamine 在 magnesium sulfate 、 magnesium bromide 作用下， 以 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 30.0h， 生成 (S,S)-<2-(tert-butyldimethylsilyloxy)-1-phenylethyl>-(2-methoxy-1-methyl-1-phenylethyl)-amine
  参考文献：
  名称：

  Highly Diastereoselective Addition of Grignard Reagents to Aliphatic, Enolizable N-Alkylketimines and 2,2-Disubstituted 1,3-Oxazolidines. Asymmetric Synthesis of the Antidepressant Cericlamine

  摘要：

  Grignard reagents were added to 2,2-disubstituted 1,3-oxazolidines and enolizable ketimines prepared from hydroxyacetone and phenylglycinol derivatives, with high to excellent diastereoselectivity, to yield 2,2-disubstituted 1,2-amino alcohol derivatives. Lewis acids had considerable influence on the yield and diastereoselectivity of the addition. This method was applied to the first asymmetric synthesis of the 5-HT reuptake inhibitor Cericlamine.

  DOI：

  10.1021/jo982222+