(2R)-2-phenyl-2-[[(1R)-1-(4,4,6,6-tetramethyl-1,3-dioxan-2-yl)propyl]amino]ethanol | 160069-68-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2R)-2-phenyl-2-[[(1R)-1-(4,4,6,6-tetramethyl-1,3-dioxan-2-yl)propyl]amino]ethanol
• CAS: 160069-68-1
• 化学式: C₁₉H₃₁NO₃
• 分子量: 321.46
• InChiKey: UGNKTXTYNVAWMZ-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-2-phenyl-2-[[(1R)-1-(4,4,6,6-tetramethyl-1,3-dioxan-2-yl)propyl]amino]ethanol 在 钯 甲酸铵 、 三乙胺 作用下， 生成 benzyl N-[(1R)-1-(4,4,6,6-tetramethyl-1,3-dioxan-2-yl)propyl]carbamate
  参考文献：
  名称：

  Enantioselective synthesis of α-amino acetals (aldehydes) via nucleophilic 1,2-addition to chiral 1,3-oxazolidines

  摘要：

  A general procedure for the diastereoselective addition of Grignard reagents to chiral 2-(4,4,6,6-tetramethyl-1,3-dioxan-2-yl)-4-substituted-1,3-oxazolidines 4 is described. Chemical yields and diastereoselectivities are generally excellent (91-100% de). The resulting amino alcohols 6 may be oxidatively or reductively cleaved to enantiomerically enriched alpha-amino acetals 3 which are useful chiral building blocks.

  DOI：

  10.1016/s0040-4039(00)78325-0
• 作为产物：
  描述：

  乙基氯化镁 、 2-(4,4,6,6-tetramethyl-1,3-dioxan-2-yl)-4-(R)-phenyl-1,3-oxazolidine 在 cerium(III) chloride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (R)-2-Phenyl-2-[(S)-1-(4,4,6,6-tetramethyl-[1,3]dioxan-2-yl)-propylamino]-ethanol 、 (2R)-2-phenyl-2-[[(1R)-1-(4,4,6,6-tetramethyl-1,3-dioxan-2-yl)propyl]amino]ethanol
  参考文献：
  名称：

  Enantioselective synthesis of α-amino acetals (aldehydes) via nucleophilic 1,2-addition to chiral 1,3-oxazolidines

  摘要：

  A general procedure for the diastereoselective addition of Grignard reagents to chiral 2-(4,4,6,6-tetramethyl-1,3-dioxan-2-yl)-4-substituted-1,3-oxazolidines 4 is described. Chemical yields and diastereoselectivities are generally excellent (91-100% de). The resulting amino alcohols 6 may be oxidatively or reductively cleaved to enantiomerically enriched alpha-amino acetals 3 which are useful chiral building blocks.

  DOI：

  10.1016/s0040-4039(00)78325-0

文献信息

• Enantioselective synthesis of α-amino acetals (aldehydes) via nucleophilic 1,2-addition to chiral 1,3-oxazolidines
  作者：K.Raman Muralidharan、Mohamed K. Mokhallalati、Lendon N. Pridgen

  DOI：10.1016/s0040-4039(00)78325-0

  日期：1994.10

  A general procedure for the diastereoselective addition of Grignard reagents to chiral 2-(4,4,6,6-tetramethyl-1,3-dioxan-2-yl)-4-substituted-1,3-oxazolidines 4 is described. Chemical yields and diastereoselectivities are generally excellent (91-100% de). The resulting amino alcohols 6 may be oxidatively or reductively cleaved to enantiomerically enriched alpha-amino acetals 3 which are useful chiral building blocks.