(R)-N-(1-hydroxymethyl)propyl-2-methyl-propaneamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-N-(1-hydroxymethyl)propyl-2-methyl-propaneamide
• 英文别名: N-[(2R)-1-hydroxybutan-2-yl]-2-methylpropanamide
• 化学式: C₈H₁₇NO₂
• 分子量: 159.228
• InChiKey: BCRZDAMCDOTLEP-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-N-(1-hydroxymethyl)propyl-2-methyl-propaneamide 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以59%的产率得到(R)-4-乙基-2-异丙基-2-恶唑啉
  参考文献：
  名称：

  (N,N) vs. (N,S) chelation of palladium in asymmetric allylic substitution using bis(thiazoline) ligands: A theoretical and experimental study

  摘要：

  New thiazoline-containing ligands including non-symmetric bis(thiazolines) and oxazoline-thiazolines were synthesized and then compared to C-2-symmetric bis(thiazolines) in the palladium-catalyzed allylic substitution. The experimental results obtained in this study support the hypothesis of a competition between the (N,N) and the (N,S) palladium chelation, when sterically hindered bis(thiazolines) are used as ligands. A quantum chemical study performed on the Pd-complexes derived from three selected ligands, two C-2-symmetric bis(thiazolines) and one oxazoline-thiazoline, also supports this hypothesis. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.04.044
• 作为产物：
  描述：

  2-氨基丁醇 、 异丁酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以95%的产率得到(R)-N-(1-hydroxymethyl)propyl-2-methyl-propaneamide
  参考文献：
  名称：

  (N,N) vs. (N,S) chelation of palladium in asymmetric allylic substitution using bis(thiazoline) ligands: A theoretical and experimental study

  摘要：

  New thiazoline-containing ligands including non-symmetric bis(thiazolines) and oxazoline-thiazolines were synthesized and then compared to C-2-symmetric bis(thiazolines) in the palladium-catalyzed allylic substitution. The experimental results obtained in this study support the hypothesis of a competition between the (N,N) and the (N,S) palladium chelation, when sterically hindered bis(thiazolines) are used as ligands. A quantum chemical study performed on the Pd-complexes derived from three selected ligands, two C-2-symmetric bis(thiazolines) and one oxazoline-thiazoline, also supports this hypothesis. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.04.044