(5S)-5-benzyl-4-isopropyl-3-propanoyl-2H-1,3,4-oxadiazinan-2-one

• 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: (5S)-5-benzyl-4-isopropyl-3-propanoyl-2H-1,3,4-oxadiazinan-2-one
• 英文别名: (5S)-5-benzyl-3-propanoyl-4-propan-2-yl-1,3,4-oxadiazinan-2-one
• 化学式: C₁₆H₂₂N₂O₃
• 分子量: 290.362
• InChiKey: ARWKTDPXIFVMJT-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S)-5-benzyl-4-isopropyl-3-propanoyl-2H-1,3,4-oxadiazinan-2-one 、 苯甲醛 在 四氯化钛 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以47%的产率得到(2'S,3'S,5S)-5-benzyl-3-(3-hydroxy-2-methyl-3-phenylpropanoyl)-4-isopropyl-2H-1,3,4-oxadiazinan-2-one
  参考文献：
  名称：

  Synthesis, reactivity and conformational stability of an l-phenylalanine derived oxadiazinanone

  摘要：

  An L-phenylalanine derived oxadiazinanone bearing an isopropyl group at the N-4-position was prepared and acylated with either hydrocinnamoyl or propanoyl chloride. These oxadiazinanones were utilized in titanium-mediated asymmetric aldol reactions with aromatic and aliphatic aldehydes. The diastereoselectivities observed from these reactions ranged from fair to very good and suggested that the N-4-isopropyl-L-phenylalanine based oxadiazinanones are conformationally and configurationally stable at the N-4-nitrogen. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.002
• 作为产物：
  描述：

  (S)-N-isopropyl(phenylalaninol) 在 盐酸 、 lithium aluminium tetrahydride 、 lithium hydride 、 sodium nitrite 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 62.0h， 生成 (5S)-5-benzyl-4-isopropyl-3-propanoyl-2H-1,3,4-oxadiazinan-2-one
  参考文献：
  名称：

  Synthesis, reactivity and conformational stability of an l-phenylalanine derived oxadiazinanone

  摘要：

  An L-phenylalanine derived oxadiazinanone bearing an isopropyl group at the N-4-position was prepared and acylated with either hydrocinnamoyl or propanoyl chloride. These oxadiazinanones were utilized in titanium-mediated asymmetric aldol reactions with aromatic and aliphatic aldehydes. The diastereoselectivities observed from these reactions ranged from fair to very good and suggested that the N-4-isopropyl-L-phenylalanine based oxadiazinanones are conformationally and configurationally stable at the N-4-nitrogen. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.09.002