3-acetyl-1-methyl-5,6-O-isopropylidene-2-oxa-3-azabicyclo[2.2.2]oct-7-ene-5,6-diol | 1229922-62-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetyl-1-methyl-5,6-O-isopropylidene-2-oxa-3-azabicyclo[2.2.2]oct-7-ene-5,6-diol
• CAS: 1229922-62-6
• 化学式: C₁₂H₁₇NO₄
• 分子量: 239.271
• InChiKey: NOKDADUVQDKZPU-WDCWCFNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.0
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  48.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-acetyl-1-methyl-5,6-O-isopropylidene-2-oxa-3-azabicyclo[2.2.2]oct-7-ene-5,6-diol 在 水 、 molybdenum hexacarbonyl 作用下， 以 乙腈 为溶剂， 以68%的产率得到(1S,2S,3S,6R)-6-acetylamino-1,2-O-isopropylidene-3-methylcyclohex-4-ene-1,2,3-triol
  参考文献：
  名称：

  Synthesis of 1,2- and 1,4-amino alcohols from 1,3-dienes via oxazines. Rearrangements of 1,4-amino alcohol derivatives to oxazolines

  摘要：

  Conjugated dienes were converted to 1,2-oxazines by reaction with an acyl nitroso dienophile. The oxazines were reduced to 1,4-N-acetylamino alcohols, which were rearranged to the corresponding oxazolines upon treatment with methanesulfonyl chloride or anhydride. The oxazolines yielded 1,2-N-acetylamino alcohols upon hydrolysis. Thus either 1,4- or 1,2-N-acetylamino alcohols are available from 1,3-dienes via this methodology. Experimental and spectral data are provided for all new compounds. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.059
• 作为产物：
  描述：

  乙酰氧肟酸 、 (3aR,7aS)-2,2,4-trimethyl-3a,7a-dihydro-1,3-benzodioxole 在 sodium periodate 作用下， 以 甲醇 为溶剂， 以720 mg的产率得到3-acetyl-1-methyl-5,6-O-isopropylidene-2-oxa-3-azabicyclo[2.2.2]oct-7-ene-5,6-diol
  参考文献：
  名称：

  Synthesis of 1,2- and 1,4-amino alcohols from 1,3-dienes via oxazines. Rearrangements of 1,4-amino alcohol derivatives to oxazolines

  摘要：

  Conjugated dienes were converted to 1,2-oxazines by reaction with an acyl nitroso dienophile. The oxazines were reduced to 1,4-N-acetylamino alcohols, which were rearranged to the corresponding oxazolines upon treatment with methanesulfonyl chloride or anhydride. The oxazolines yielded 1,2-N-acetylamino alcohols upon hydrolysis. Thus either 1,4- or 1,2-N-acetylamino alcohols are available from 1,3-dienes via this methodology. Experimental and spectral data are provided for all new compounds. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.059