(4R,6S)-4-hydroxymethyl-6-methyl-1,3-oxazin-2-one | 676473-31-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (4R,6S)-4-hydroxymethyl-6-methyl-1,3-oxazin-2-one
• 英文别名: (4R,6S)-4-(hydroxymethyl)-6-methyl-1,3-oxazinan-2-one
• CAS: 676473-31-7
• 化学式: C₆H₁₁NO₃
• 分子量: 145.158
• InChiKey: WNWNDDXBUWHURV-CRCLSJGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (4R,6S)-4-hydroxymethyl-6-methyl-1,3-oxazin-2-one 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以71%的产率得到(2R,4S)-2-amino-pentane-1,4-diol
  参考文献：
  名称：

  Novel enantiomerically pure 2-amino-1,4-diols from chiral 4-hydroxymethyl-5-iodo-1,3-oxazin-2-ones

  摘要：

  Reduction of (4S,5S,6S)-4-hydroxymethyl-5-iodo-6-methyl-1,3-oxazin-2-one 2a and (4S,5S,6R)-4-hydroxyrncthyl-5-iodo-6-phenyl-1,3-oxazin-2-one 2b with tributyltin hydride in ethanol afforded 1,3-oxazin-2-one 3a and 1,3-oxazolidin-2-one 4b, respectively. Hydrolysis of 3a and 4b under basic conditions led to enantiomerically pure aminodiols 1a and 1b. Reduction of 2b in refluxing toluene led to the unexpected bicyclic tetrahydrofuro[3a,d]-1,3-oxazolidin-2-one 5 as the sole product. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.12.022
• 作为产物：
  描述：

  (4S,5S,6S)-1-aza-5-iodo-4,9,9-trimethyl-3,8-dioxa-2-oxobicyclo<4.3.0>nonane 在 偶氮二异丁腈 、 三正丁基氢锡 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 22.0h， 生成 (4R,6S)-4-hydroxymethyl-6-methyl-1,3-oxazin-2-one
  参考文献：
  名称：

  Novel enantiomerically pure 2-amino-1,4-diols from chiral 4-hydroxymethyl-5-iodo-1,3-oxazin-2-ones

  摘要：

  Reduction of (4S,5S,6S)-4-hydroxymethyl-5-iodo-6-methyl-1,3-oxazin-2-one 2a and (4S,5S,6R)-4-hydroxyrncthyl-5-iodo-6-phenyl-1,3-oxazin-2-one 2b with tributyltin hydride in ethanol afforded 1,3-oxazin-2-one 3a and 1,3-oxazolidin-2-one 4b, respectively. Hydrolysis of 3a and 4b under basic conditions led to enantiomerically pure aminodiols 1a and 1b. Reduction of 2b in refluxing toluene led to the unexpected bicyclic tetrahydrofuro[3a,d]-1,3-oxazolidin-2-one 5 as the sole product. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.12.022