2-[(1R,3S,4S)-3-bromo-4-methoxy-4-methylcyclohexyl]-2-methyloxirane | 1025858-03-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: 2-[(1R,3S,4S)-3-bromo-4-methoxy-4-methylcyclohexyl]-2-methyloxirane
• CAS: 1025858-03-0
• 化学式: C₁₁H₁₉BrO₂
• 分子量: 263.175
• InChiKey: FKHNBILUIHDLRB-LCVSCUNMSA-N

物化性质

• 沸点：
  278.2±40.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[(1R,3S,4S)-3-bromo-4-methoxy-4-methylcyclohexyl]-2-methyloxirane 在 氯化铵 、 锌 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以8.4 g的产率得到(R)-8,9-limonene oxide
  参考文献：
  名称：

  Chemoselective Formation of 8,9‐Epoxy‐limonene

  摘要：

  We present here a synthetic path to produce, exclusively, 8,9-epoxy-limonene in 75% overall yields. We developed a three step synthetic route. First, the 1,2-double bond of limonene was protected by the formation of the bromo-methylether by cohalogenation with NBS in MeOH. Then, this product was oxidized by m-chloro-perbenzoic acid to give the corresponding epoxides. Finally, the 1,2-double bond was restored by a reaction with NH4Cl/Zn leading to 8,9-epoxy-limonene. The great advantage of this methodology is that the intermediate purification steps are not necessary.

  DOI：

  10.1081/scc-200057232
• 作为产物：
  描述：

  甜橙提取物 在 N-溴代丁二酰亚胺(NBS) 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 生成 2-[(1R,3S,4S)-3-bromo-4-methoxy-4-methylcyclohexyl]-2-methyloxirane
  参考文献：
  名称：

  Chemoselective Formation of 8,9‐Epoxy‐limonene

  摘要：

  We present here a synthetic path to produce, exclusively, 8,9-epoxy-limonene in 75% overall yields. We developed a three step synthetic route. First, the 1,2-double bond of limonene was protected by the formation of the bromo-methylether by cohalogenation with NBS in MeOH. Then, this product was oxidized by m-chloro-perbenzoic acid to give the corresponding epoxides. Finally, the 1,2-double bond was restored by a reaction with NH4Cl/Zn leading to 8,9-epoxy-limonene. The great advantage of this methodology is that the intermediate purification steps are not necessary.

  DOI：

  10.1081/scc-200057232

文献信息

• Chemoselective Formation of 8,9‐Epoxy‐limonene
  作者：Queli A. R. Almeida、Joel Jones

  DOI：10.1081/scc-200057232

  日期：2005.5.1

  We present here a synthetic path to produce, exclusively, 8,9-epoxy-limonene in 75% overall yields. We developed a three step synthetic route. First, the 1,2-double bond of limonene was protected by the formation of the bromo-methylether by cohalogenation with NBS in MeOH. Then, this product was oxidized by m-chloro-perbenzoic acid to give the corresponding epoxides. Finally, the 1,2-double bond was restored by a reaction with NH4Cl/Zn leading to 8,9-epoxy-limonene. The great advantage of this methodology is that the intermediate purification steps are not necessary.