(4R,5R)-N-(4-aminobutyl)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxamide | 935659-76-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-N-(4-aminobutyl)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxamide
• CAS: 935659-76-0
• 化学式: C₁₁H₂₂N₂O₄
• 分子量: 246.307
• InChiKey: JREFXSGGHGYEDF-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  93.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5R)-N-(4-aminobutyl)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxamide 、 4-碘甲苯 在 copper(l) iodide 3,4,7,8-四甲基-1,10-菲罗啉 、 3 A molecular sieve 、 caesium carbonate 作用下， 以81%的产率得到(4S,5S)-N-(4-aminobutyl)-2,2-dimethyl-5-[(4-methylphenoxy)methyl]-1,3-dioxolane-4-carboxamide
  参考文献：
  名称：

  N- versus O-Arylation of Aminoalcohols:  Orthogonal Selectivity in Copper-Based Catalysts

  摘要：

  Two complementary protocols for copper-catalyzed arylation of aminoalcohols were developed. Selective N-arylation was accomplished at room temperature using 2-isobutyrylcyclohexanone (a beta-diketone) as supporting ligand, while selective O-arylation required the use of 3,4,7,8-tetramethylphenanthroline at 80-110 degrees C. Systematic examination of the reaction scope revealed that high levels of selectivity are achieved for a variety of substrates, provided that nonchelating (or weakly chelating) aminoalcohols are used. The generality of the method was highlighted by the synthesis, in a pairwise fashion, of a number of functionalized N- and O-arylated aminoalcohols.

  DOI：

  10.1021/ja068926f
• 作为产物：
  描述：

  D-erythronolactone acetonide 、 四亚甲基二胺 以 甲醇 为溶剂， 反应 16.5h， 以80%的产率得到(4R,5R)-N-(4-aminobutyl)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxamide
  参考文献：
  名称：

  N- versus O-Arylation of Aminoalcohols:  Orthogonal Selectivity in Copper-Based Catalysts

  摘要：

  Two complementary protocols for copper-catalyzed arylation of aminoalcohols were developed. Selective N-arylation was accomplished at room temperature using 2-isobutyrylcyclohexanone (a beta-diketone) as supporting ligand, while selective O-arylation required the use of 3,4,7,8-tetramethylphenanthroline at 80-110 degrees C. Systematic examination of the reaction scope revealed that high levels of selectivity are achieved for a variety of substrates, provided that nonchelating (or weakly chelating) aminoalcohols are used. The generality of the method was highlighted by the synthesis, in a pairwise fashion, of a number of functionalized N- and O-arylated aminoalcohols.

  DOI：

  10.1021/ja068926f