(2R,4R)-N-(3,4-dimethoxybenzyl)-2,4-diphenyl-1,3-oxazolidine | 215870-51-2

• 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: (2R,4R)-N-(3,4-dimethoxybenzyl)-2,4-diphenyl-1,3-oxazolidine
• 英文别名: (2R,4R)-3-[(3,4-dimethoxyphenyl)methyl]-2,4-diphenyl-1,3-oxazolidine
• CAS: 215870-51-2
• 化学式: C₂₄H₂₅NO₃
• 分子量: 375.467
• InChiKey: VINCNISPOMNMPM-XUZZJYLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲基溴化镁 、 (2R,4R)-N-(3,4-dimethoxybenzyl)-2,4-diphenyl-1,3-oxazolidine 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 (1R,1'R)-N-(2'-hydroxy-1'-phenylethyl)-N-(3,4-dimethoxybenzyl)-1-phenylethylamine 、 (1S,1'R)-N-(2'-hydroxy-1'-phenylethyl)-N-(3,4-dimethoxybenzyl)-1-phenylethylamine
  参考文献：
  名称：

  Stereocontrolled Addition of Grignard Reagents to Chiral 1,3-Oxazolidines Having N-Methoxybenzyl Groups: Effect of N-Substituent in Diastereoselectivity

  摘要：

  Chiral 1,3-oxazolidines having various N-methoxybenzyl groups were synthesized from (R)-phenylglycinol in three steps. The reactions of chiral 1,3-oxazolidines with Grignard reagents proceeded gently to give the corresponding chiral amines in quantitative yield and high diastereoselectivity. The best results regarding diastereoselectivity were achieved using a chiral 1,3-oxazolidine having N-2,4,6-trimethoxybenzyl moiety. These nitrogen functional groups could be easily removed from the chiral amines using TFA.

  DOI：

  10.3987/com-98-8211
• 作为产物：
  描述：

  D-苯甘氨醇 在 3 A molecular sieve 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 (2R,4R)-N-(3,4-dimethoxybenzyl)-2,4-diphenyl-1,3-oxazolidine
  参考文献：
  名称：

  Stereocontrolled Addition of Grignard Reagents to Chiral 1,3-Oxazolidines Having N-Methoxybenzyl Groups: Effect of N-Substituent in Diastereoselectivity

  摘要：

  Chiral 1,3-oxazolidines having various N-methoxybenzyl groups were synthesized from (R)-phenylglycinol in three steps. The reactions of chiral 1,3-oxazolidines with Grignard reagents proceeded gently to give the corresponding chiral amines in quantitative yield and high diastereoselectivity. The best results regarding diastereoselectivity were achieved using a chiral 1,3-oxazolidine having N-2,4,6-trimethoxybenzyl moiety. These nitrogen functional groups could be easily removed from the chiral amines using TFA.

  DOI：

  10.3987/com-98-8211