(1R,2R,4S,6R)-4-isopropenyl-1,3,3-trimethyl-7-oxabicyclo[4.1.0]hept-2-yl acetate | 1292295-87-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1R,2R,4S,6R)-4-isopropenyl-1,3,3-trimethyl-7-oxabicyclo[4.1.0]hept-2-yl acetate
• 英文别名: [(1R,2R,4S,6R)-1,3,3-trimethyl-4-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptan-2-yl] acetate
• CAS: 1292295-87-4
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: CDZLQDIZPLJFJF-FMCLSXCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2R,4S,6R)-4-isopropenyl-1,3,3-trimethyl-7-oxabicyclo[4.1.0]hept-2-yl acetate 在 碳酸氢钠 、 臭氧 、 copper diacetate 、 ferrous(II) sulfate heptahydrate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.25h， 以47%的产率得到(1R,2R,4R,6R)-4-acetyl-1,3,3-trimethyl-7-oxabicyclo[4.1.0]hept-2-yl acetate
  参考文献：
  名称：

  Efficient synthesis of (1R,4S,6R)-4-Isopropenyl-1,3,3-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one

  摘要：

  A simple and convenient one-pot synthesis of (1R,4S,6R)-4-isopropenyl-1,3,3-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one was developed consisting in a thermodynamic methylation of carvone (NaH, MeI, THF, 20 degrees C) followed by the epoxidation with alkalinized hydrogen peroxide. The reduction of the obtained epoxyketone with sodium borohydride proceeded stereoselectively to give a beta-alcohol. The attempts to convert its isopropenyl fragment into an acetate group by a rearrangement of products or intermediates of the oxidative fragmentation resulted only in obtaining intermediate acyl derivatives.

  DOI：

  10.1134/s1070428011020047
• 作为产物：
  描述：

  (R)-Carvone 在 吡啶 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 40.25h， 生成 (1R,2R,4S,6R)-4-isopropenyl-1,3,3-trimethyl-7-oxabicyclo[4.1.0]hept-2-yl acetate
  参考文献：
  名称：

  Efficient synthesis of (1R,4S,6R)-4-Isopropenyl-1,3,3-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one

  摘要：

  A simple and convenient one-pot synthesis of (1R,4S,6R)-4-isopropenyl-1,3,3-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one was developed consisting in a thermodynamic methylation of carvone (NaH, MeI, THF, 20 degrees C) followed by the epoxidation with alkalinized hydrogen peroxide. The reduction of the obtained epoxyketone with sodium borohydride proceeded stereoselectively to give a beta-alcohol. The attempts to convert its isopropenyl fragment into an acetate group by a rearrangement of products or intermediates of the oxidative fragmentation resulted only in obtaining intermediate acyl derivatives.

  DOI：

  10.1134/s1070428011020047