(3aR,5aR,8aR,8bS)-2,2,7-trimethyl-4-cyclohexyl-3a,5a,8a,8b-tetrahydro[1,3]dioxolo[4,5-e][1,3]benzoxazole | 1229922-79-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,5aR,8aR,8bS)-2,2,7-trimethyl-4-cyclohexyl-3a,5a,8a,8b-tetrahydro[1,3]dioxolo[4,5-e][1,3]benzoxazole
• CAS: 1229922-79-5
• 化学式: C₁₇H₂₅NO₃
• 分子量: 291.39
• InChiKey: XNOJQDWWFWPBHT-FPCVCCKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  (1S,2R,5R,6S)-6-acetylamino-1,2-O-isopropylidene-5-chloro-3-cyclohexylcyclohex-3-ene-1,2-diol 在 三乙胺 作用下， 生成 (3aR,5aR,8aR,8bS)-2,2,7-trimethyl-4-cyclohexyl-3a,5a,8a,8b-tetrahydro[1,3]dioxolo[4,5-e][1,3]benzoxazole
  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.