(1R,1'R)-N-benzyl-1-phenyl-1'-methyl-2,2'-dihydroxydiethylamine

• 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: (1R,1'R)-N-benzyl-1-phenyl-1'-methyl-2,2'-dihydroxydiethylamine
• 英文别名: (2R)-2-[benzyl-[(1R)-2-hydroxy-1-phenylethyl]amino]propan-1-ol
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: NQTHPRABFPACRR-QAPCUYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,1'R)-N-benzyl-1-phenyl-1'-methyl-2,2'-dihydroxydiethylamine 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以71%的产率得到D-氨基丙醇
  参考文献：
  名称：

  Stereoselective Synthesis of Optically Active Diethanolamines Utilizing Diastereoselective Reaction of 1,3-Oxazolidines with Grignard Reagents

  摘要：

  The highly diastereoselective addition of isopropoxydimethylsilylmethylmagnesium chloride to N-benzyl-1,3-oxazolidines derived from (R)-phenyl-glycinol, followed by oxidation of adducts with hydrogen peroxide in the presence of potassium fluoride, provided the 1-substituted (1R, 1'R)-N-benzyl-1'-phenyl-2,2'-dihydroxydiethylamines (1a-d).

  DOI：

  10.3987/com-95-7116
• 作为产物：
  描述：

  magnesium,methanidyl-dimethyl-propan-2-yloxysilane,chloride 、 (-)-(2R,4R)-3-benzyl-2-methyl-4-phenyloxazolidine 在 potassium fluoride 、 双氧水 、 碳酸氢钠 作用下， 生成 (1R,1'R)-N-benzyl-1-phenyl-1'-methyl-2,2'-dihydroxydiethylamine
  参考文献：
  名称：

  Stereoselective Synthesis of Optically Active Diethanolamines Utilizing Diastereoselective Reaction of 1,3-Oxazolidines with Grignard Reagents

  摘要：

  The highly diastereoselective addition of isopropoxydimethylsilylmethylmagnesium chloride to N-benzyl-1,3-oxazolidines derived from (R)-phenyl-glycinol, followed by oxidation of adducts with hydrogen peroxide in the presence of potassium fluoride, provided the 1-substituted (1R, 1'R)-N-benzyl-1'-phenyl-2,2'-dihydroxydiethylamines (1a-d).

  DOI：

  10.3987/com-95-7116

文献信息

• Stereoselective Synthesis of Optically Active Diethanolamines Utilizing Diastereoselective Reaction of 1,3-Oxazolidines with Grignard Reagents
  作者：Kimio Higashiyama、Katuyuki Nakagawa、Hiroshi Takahashi

  DOI：10.3987/com-95-7116

  日期：——

  The highly diastereoselective addition of isopropoxydimethylsilylmethylmagnesium chloride to N-benzyl-1,3-oxazolidines derived from (R)-phenyl-glycinol, followed by oxidation of adducts with hydrogen peroxide in the presence of potassium fluoride, provided the 1-substituted (1R, 1'R)-N-benzyl-1'-phenyl-2,2'-dihydroxydiethylamines (1a-d).