(3aS,4R,5S,7aS)-2,3a-dimethyl-4,5-O-isopropylidene-3a,4,5,7a-tetrahydrobenzo[d]oxazole-4,5-diol | 1229922-72-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4R,5S,7aS)-2,3a-dimethyl-4,5-O-isopropylidene-3a,4,5,7a-tetrahydrobenzo[d]oxazole-4,5-diol
• CAS: 1229922-72-8
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: VBDHZCVPEDAGBI-GMOBBJLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  40.05
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  N-((3aR,4S,7R,7aS)-7-hydroxy-2,2,4-trimethyl-3a,4,7,7a-tetrahydrobenzo[d][1,3]dioxol-4-yl)acetamide 在 甲基磺酰氯 、 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 以57%的产率得到(3aS,4R,5S,7aS)-2,3a-dimethyl-4,5-O-isopropylidene-3a,4,5,7a-tetrahydrobenzo[d]oxazole-4,5-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

文献信息

• Synthesis of 1,2- and 1,4-amino alcohols from 1,3-dienes via oxazines. Rearrangements of 1,4-amino alcohol derivatives to oxazolines
  作者：Lukas Werner、Jason Reed Hudlicky、Martina Wernerova、Tomas Hudlicky

  DOI：10.1016/j.tet.2010.03.059

  日期：2010.5

  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.