(1R,4R,6R)-4-acetyl-1,3,3-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one | 1292295-88-5

• 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,4R,6R)-4-acetyl-1,3,3-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one
• CAS: 1292295-88-5
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: PJVTVWLSMFGORS-VAOFZXAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  46.67
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,4R,6R)-4-acetyl-1,3,3-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one 在 双氧水 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 以47%的产率得到(3R,5R,6S)-3-acetyl-5,6-dihydroxy-2,2,6-trimethylcyclohexan-1-one
  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：

  (1R,4S,6R)-1,3,3-trimethyl-4-(prop-1-en-2-yl)-7-oxa-bicyclo[4.1.0]heptan-2-one 在 臭氧 、 4-二甲氨基吡啶 、 乙酸酐 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 7.5h， 以50%的产率得到(1R,4R,6R)-4-acetyl-1,3,3-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one
  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

文献信息

• Efficient synthesis of (1R,4S,6R)-4-Isopropenyl-1,3,3-trimethyl-7-oxabicyclo[4.1.0]heptan-2-one
  作者：N. K. Selezneva、F. A. Gimalova、R. F. Valeev、M. S. Miftakhov

  DOI：10.1134/s1070428011020047

  日期：2011.2

  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.