(S,S)-2-(2-methoxy-1-methyl-1-phenylethylamino)-2-phenylethanol | 222733-14-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S,S)-2-(2-methoxy-1-methyl-1-phenylethylamino)-2-phenylethanol
• 英文别名: (2S)-2-[[(2S)-1-methoxy-2-phenylpropan-2-yl]amino]-2-phenylethanol
• CAS: 222733-14-4
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: ZTSMUGPOQJWPTG-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S,S)-2-(2-methoxy-1-methyl-1-phenylethylamino)-2-phenylethanol 在 lead(IV) acetate 、 SCX column 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 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：

  L-苯甘氨醇 在 盐酸 、 4-二甲氨基吡啶 、 乙醇 、 magnesium sulfate 、 三乙胺 、 magnesium bromide 作用下， 以 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 55.0h， 生成 (S,S)-2-(2-methoxy-1-methyl-1-phenylethylamino)-2-phenylethanol
  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+

文献信息

• Highly Diastereoselective Addition of Grignard Reagents to Aliphatic, Enolizable <i>N</i>-Alkylketimines and 2,2-Disubstituted 1,3-Oxazolidines. Asymmetric Synthesis of the Antidepressant Cericlamine
  作者：Arno G. Steinig、Denice M. Spero

  DOI：10.1021/jo982222+

  日期：1999.4.1

  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.