(4S)-1-tert-butyldimethylsilyloxymethyl-1,2-epoxy-4-isopropylcyclohexane | 913548-03-5

• 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: (4S)-1-tert-butyldimethylsilyloxymethyl-1,2-epoxy-4-isopropylcyclohexane
• 英文别名: tert-butyl-dimethyl-[[(4S)-4-propan-2-yl-7-oxabicyclo[4.1.0]heptan-1-yl]methoxy]silane
• CAS: 913548-03-5
• 化学式: C₁₆H₃₂O₂Si
• 分子量: 284.514
• InChiKey: OAGQBXBHGCUABU-HLIUYOAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  5
• 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：

  (4S)-1-tert-butyldimethylsilyloxymethyl-1,2-epoxy-4-isopropylcyclohexane 在 sodium periodate 、 四丁基氟化铵 、 sodium hydride 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 7.5h， 生成 cis-p-menth-2-en-1-ol
  参考文献：
  名称：

  Synthesis of (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus, its racemate, (1R,4R)- and (1S,4S)-isomers

  摘要：

  (S)-Perillyl alcohol was converted to (R)-cryptone (91.5-93% ee) in six steps, which was then treated with methyllithium to give (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus. The racemic pheromone was also prepared by methylation of (+/-)-cryptone. Both (1R,4R)- and (1S,4S)-isomers (98% ee) of the pheromone were synthesized from the enantiomers of dihydrolimonene oxide. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.030
• 作为产物：
  描述：

  (S)-(-)-紫苏醇 在 platinum(IV) oxide 、 bis(acetylacetonate)oxovanadium 咪唑 、 叔丁基过氧化氢 、 氢气 作用下， 以 正己烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.5h， 生成 (4S)-1-tert-butyldimethylsilyloxymethyl-1,2-epoxy-4-isopropylcyclohexane
  参考文献：
  名称：

  Synthesis of (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus, its racemate, (1R,4R)- and (1S,4S)-isomers

  摘要：

  (S)-Perillyl alcohol was converted to (R)-cryptone (91.5-93% ee) in six steps, which was then treated with methyllithium to give (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus. The racemic pheromone was also prepared by methylation of (+/-)-cryptone. Both (1R,4R)- and (1S,4S)-isomers (98% ee) of the pheromone were synthesized from the enantiomers of dihydrolimonene oxide. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.030

文献信息

• Synthesis of (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus, its racemate, (1R,4R)- and (1S,4S)-isomers
  作者：Kenji Mori

  DOI：10.1016/j.tetasy.2006.07.030

  日期：2006.8

  (S)-Perillyl alcohol was converted to (R)-cryptone (91.5-93% ee) in six steps, which was then treated with methyllithium to give (1S,4R)-4-isopropyl-1-methyl-2-cyclohexen-1-ol, the aggregation pheromone of the ambrosia beetle Platypus quercivorus. The racemic pheromone was also prepared by methylation of (+/-)-cryptone. Both (1R,4R)- and (1S,4S)-isomers (98% ee) of the pheromone were synthesized from the enantiomers of dihydrolimonene oxide. (c) 2006 Elsevier Ltd. All rights reserved.