(1S,2S,3S,6R)-6-acetylamino-1,2-O-isopropylidene-3-cyclohexylcyclohex-4-ene-1,2,3-triol | 1229922-77-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,3S,6R)-6-acetylamino-1,2-O-isopropylidene-3-cyclohexylcyclohex-4-ene-1,2,3-triol
• 英文别名: N-[(3aS,4R,7S,7aS)-7-cyclohexyl-7-hydroxy-2,2-dimethyl-4,7a-dihydro-3aH-1,3-benzodioxol-4-yl]acetamide
• CAS: 1229922-77-3
• 化学式: C₁₇H₂₇NO₄
• 分子量: 309.406
• InChiKey: JMNVUYKVSNZVQQ-WBTNSWJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S,3S,6R)-6-acetylamino-1,2-O-isopropylidene-3-cyclohexylcyclohex-4-ene-1,2,3-triol 在 甲基磺酰氯 、 三乙胺 、 乙醇 、 sodium hydroxide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 17.0h， 以58%的产率得到N-((3aS,4R,5R,7aR)-7-cyclohexyl-5-hydroxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxol-4-yl)acetamide
  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：

  3-acetyl-1-cyclohexyl-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69%的产率得到(1S,2S,3S,6R)-6-acetylamino-1,2-O-isopropylidene-3-cyclohexylcyclohex-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