(3aS,4S,5R,7aR)-4-acetamido-7-cyclohexyl-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxol-5-yl methanesulfonate | 1229922-83-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4S,5R,7aR)-4-acetamido-7-cyclohexyl-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxol-5-yl methanesulfonate
• CAS: 1229922-83-1
• 化学式: C₁₈H₂₉NO₆S
• 分子量: 387.497
• InChiKey: HXGKBCVHXYQTML-VQHPVUNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  90.93
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3aS,4S,5R,7aR)-4-acetamido-7-cyclohexyl-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxol-5-yl methanesulfonate 、 甲基磺酰氯 、 三乙胺 以 二氯甲烷 为溶剂， 反应 0.08h， 以40%的产率得到(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
• 作为产物：
  描述：

  (1S,2S,3S,6R)-6-acetylamino-1,2-O-isopropylidene-3-cyclohexylcyclohex-4-ene-1,2,3-triol 、 甲基磺酰氯 在 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 (3aS,4S,5R,7aR)-4-acetamido-7-cyclohexyl-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxol-5-yl 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