(1S,2R,5S,6S)-6-acetylamino-1,2-O-isopropylidene-5-chloro-3-cyclohexylcyclohex-3-ene-1,2-diol | 1229922-86-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,5S,6S)-6-acetylamino-1,2-O-isopropylidene-5-chloro-3-cyclohexylcyclohex-3-ene-1,2-diol
• CAS: 1229922-86-4
• 化学式: C₁₇H₂₆ClNO₃
• 分子量: 327.851
• InChiKey: HTYLCFQVQVGNGR-JJXSEGSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,5S,6S)-6-acetylamino-1,2-O-isopropylidene-5-chloro-3-cyclohexylcyclohex-3-ene-1,2-diol 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
• 作为产物：
  描述：

  N-((3aS,4R,5R,7aR)-7-cyclohexyl-5-hydroxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxol-4-yl)acetamide 、 甲基磺酰氯 、 三乙胺 以 1,2-二氯乙烷 为溶剂， 生成 (1S,2R,5S,6S)-6-acetylamino-1,2-O-isopropylidene-5-chloro-3-cyclohexylcyclohex-3-ene-1,2-diol 、 、 (3aS,4R,5S,7aR)-4-acetamido-7-cyclohexyl-N,N,N-triethyl-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxol-5-ammonium methanesulfonate
  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