(4S,6R)-1-methyl-6-(4'-nitrobenzoyloxy)-4-(methoxycarbonyl)cyclohexene | 607353-60-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S,6R)-1-methyl-6-(4'-nitrobenzoyloxy)-4-(methoxycarbonyl)cyclohexene
• 英文别名: [(1R,5S)-5-methoxycarbonyl-2-methylcyclohex-2-en-1-yl] 4-nitrobenzoate
• CAS: 607353-60-6
• 化学式: C₁₆H₁₇NO₆
• 分子量: 319.314
• InChiKey: YGAUSOHRQQLIPM-GXTWGEPZSA-N

物化性质

• 沸点：
  448.9±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,6R)-1-methyl-6-(4'-nitrobenzoyloxy)-4-(methoxycarbonyl)cyclohexene 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以93%的产率得到(4S,6R)-6-hydroxy-1-methyl-4-(methoxycarbonyl)cyclohexene
  参考文献：
  名称：

  A Convenient, Large Scale Synthesis oftrans-(+)-Sobrerol

  摘要：

  A convenient and highly efficient synthesis of optically pure trans(+)-sobrerol (1), starting from methyl 3,5-dihydroxy-4-methyl benzoate 2 in 8 steps with overall yield 26%, is reported. The key intermediate 4 is prepared in remarkably high yield by selectively esterification of 3 using lipase as catalyst. A critical step to stereoselectively inverse the configuration of 7 is realized under Mistunobu conditions.

  DOI：

  10.1081/scc-120021040
• 作为产物：
  描述：

  (1R,3S,4S,5R)-5-acetoxy-3-hydroxy-4-methyl-1-(methoxycarbonyl)cyclohexane 在 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 (4S,6R)-1-methyl-6-(4'-nitrobenzoyloxy)-4-(methoxycarbonyl)cyclohexene
  参考文献：
  名称：

  A Convenient, Large Scale Synthesis oftrans-(+)-Sobrerol

  摘要：

  A convenient and highly efficient synthesis of optically pure trans(+)-sobrerol (1), starting from methyl 3,5-dihydroxy-4-methyl benzoate 2 in 8 steps with overall yield 26%, is reported. The key intermediate 4 is prepared in remarkably high yield by selectively esterification of 3 using lipase as catalyst. A critical step to stereoselectively inverse the configuration of 7 is realized under Mistunobu conditions.

  DOI：

  10.1081/scc-120021040

文献信息

• A Convenient, Large Scale Synthesis of<i>trans</i>-(+)-Sobrerol
  作者：Qiuan Wang、Yanlin Li、Qingqi Chen

  DOI：10.1081/scc-120021040

  日期：2003.7

  A convenient and highly efficient synthesis of optically pure trans(+)-sobrerol (1), starting from methyl 3,5-dihydroxy-4-methyl benzoate 2 in 8 steps with overall yield 26%, is reported. The key intermediate 4 is prepared in remarkably high yield by selectively esterification of 3 using lipase as catalyst. A critical step to stereoselectively inverse the configuration of 7 is realized under Mistunobu conditions.