(4S,5R,6S)-3,4,5,6-tetrahydro-4-benzyl-5-hydroxy-6-(2-methylpropyl)-2H-1,3-oxazin-2-one | 182204-90-6

• 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: (4S,5R,6S)-3,4,5,6-tetrahydro-4-benzyl-5-hydroxy-6-(2-methylpropyl)-2H-1,3-oxazin-2-one
• 英文别名: (4S,5R,6S)-4-benzyl-5-hydroxy-6-(2-methylpropyl)-1,3-oxazinan-2-one
• CAS: 182204-90-6
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: OCTCCOLISBHJBX-MELADBBJSA-N

物化性质

• 沸点：
  476.5±34.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5R,6S)-3,4,5,6-tetrahydro-4-benzyl-5-hydroxy-6-(2-methylpropyl)-2H-1,3-oxazin-2-one 在 lithium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以96%的产率得到(2S,3R,4S)-2-Amino-6-methyl-1-phenyl-heptane-3,4-diol
  参考文献：
  名称：

  Selective Inversion of the Proximal or Distal Hydroxyl Groups in syn,syn-3-[N-(Alkoxycarbonyl)amino] 1,2-Diols via Cyclic Sulfates

  摘要：

  The formation of cyclic sulfates (4) from syn,syn-3-[N-(benzyloxycarbonyl)amino] 1,2-diols provides a common intermediate to access other diastereomers via two inversion procedures. Thermolysis of the cyclic sulfates in acetonitrile normally leads to inversion of the distal hydroxyl group to form a 1,3-oxazin-2-one (6). Catalytic hydrogenation of the cyclic sulfates under basic conditions (NEt(3)) results in inversion at the proximal hydroxyl group to form a 1,3-oxazolidin-2-one (5).

  DOI：

  10.1021/jo961060j
• 作为产物：
  描述：

  (2S,3R,4R)-2--6-methyl-1-phenylheptane-3,4-diol 在 palladium on activated charcoal ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 硫酸 、 氢气 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 19.58h， 生成 (4S,5R,6S)-3,4,5,6-tetrahydro-4-benzyl-5-hydroxy-6-(2-methylpropyl)-2H-1,3-oxazin-2-one
  参考文献：
  名称：

  Selective Inversion of the Proximal or Distal Hydroxyl Groups in syn,syn-3-[N-(Alkoxycarbonyl)amino] 1,2-Diols via Cyclic Sulfates

  摘要：

  The formation of cyclic sulfates (4) from syn,syn-3-[N-(benzyloxycarbonyl)amino] 1,2-diols provides a common intermediate to access other diastereomers via two inversion procedures. Thermolysis of the cyclic sulfates in acetonitrile normally leads to inversion of the distal hydroxyl group to form a 1,3-oxazin-2-one (6). Catalytic hydrogenation of the cyclic sulfates under basic conditions (NEt(3)) results in inversion at the proximal hydroxyl group to form a 1,3-oxazolidin-2-one (5).

  DOI：

  10.1021/jo961060j

文献信息

• Selective Inversion of the Proximal or Distal Hydroxyl Groups in <i>syn,syn</i>-3-[<i>N</i>-(Alkoxycarbonyl)amino] 1,2-Diols via Cyclic Sulfates
  作者：Scott J. Kemp、Jianming Bao、Steven F. Pedersen

  DOI：10.1021/jo961060j

  日期：1996.1.1

  The formation of cyclic sulfates (4) from syn,syn-3-[N-(benzyloxycarbonyl)amino] 1,2-diols provides a common intermediate to access other diastereomers via two inversion procedures. Thermolysis of the cyclic sulfates in acetonitrile normally leads to inversion of the distal hydroxyl group to form a 1,3-oxazin-2-one (6). Catalytic hydrogenation of the cyclic sulfates under basic conditions (NEt(3)) results in inversion at the proximal hydroxyl group to form a 1,3-oxazolidin-2-one (5).