(S)-N-(1-iso-butyl-2-hydroxyethyl)benzoylformamide | 852249-79-7

• 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: (S)-N-(1-iso-butyl-2-hydroxyethyl)benzoylformamide
• CAS: 852249-79-7
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: DJOWBHGDYJXFQH-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.4
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-N-(1-iso-butyl-2-hydroxyethyl)benzoylformamide 在 氯化亚砜 、 sodium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 (S)-2-(diphenylhydroxy)methyl-4-iso-butyl-2-oxazoline
  参考文献：
  名称：

  Synthesis of new chiral hydroxy oxazolines and their use in the catalytic asymmetric phenyl transfer to aldehydes

  摘要：

  Starting either from benzoylformic acid or ethyl oxamate and enantiopure beta-amino alcohols, several chiral alpha-hydroxy oxazolines have been prepared by short synthetic routes. Subsequently, they have been employed in the catalytic asymmetric phenyl transfer to various aldehydes, using a mixture of triphenylborane and diethylzinc as the phenyl source. The corresponding secondary alcohols were obtained with good enantioselectivities (up to 81% ee) and up to 92% yield. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.038
• 作为产物：
  描述：

  L-亮氨醇 、 苯甲酰甲酸 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以61%的产率得到(S)-N-(1-iso-butyl-2-hydroxyethyl)benzoylformamide
  参考文献：
  名称：

  Synthesis of new chiral hydroxy oxazolines and their use in the catalytic asymmetric phenyl transfer to aldehydes

  摘要：

  Starting either from benzoylformic acid or ethyl oxamate and enantiopure beta-amino alcohols, several chiral alpha-hydroxy oxazolines have been prepared by short synthetic routes. Subsequently, they have been employed in the catalytic asymmetric phenyl transfer to various aldehydes, using a mixture of triphenylborane and diethylzinc as the phenyl source. The corresponding secondary alcohols were obtained with good enantioselectivities (up to 81% ee) and up to 92% yield. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.01.038