(4R,5S,8R)-5-isopropyl-8-methyl-1-oxaspiro[3.5]nonane | 196792-59-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (4R,5S,8R)-5-isopropyl-8-methyl-1-oxaspiro[3.5]nonane
• 英文别名: (4R,5S,8R)-8-methyl-5-propan-2-yl-1-oxaspiro[3.5]nonane
• CAS: 196792-59-3
• 化学式: C₁₂H₂₂O
• 分子量: 182.306
• InChiKey: QSXSQWAIGOHWPS-WOPDTQHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4R,5S,8R)-5-isopropyl-8-methyl-1-oxaspiro[3.5]nonane 在 4,4'-二叔丁基苯并 、 重水 、 lithium 作用下， 生成 (1S,5S,5R)-1-(2-deuterioethyl)-2-isopropyl-5-methylcyclohexanol
  参考文献：
  名称：

  Enantiomerically pure γ-oxidofunctionalised organolithium compounds from chiral oxetanes

  摘要：

  The reductive opening of chiral oxetanes 1, ent-1, 4 and 7 with lithium powder and a catalytic amount of DTBB (5 mol%) in THF at 0 degrees C or -20 degrees C, followed by treatment with different electrophiles [H2O, D2O, (BuCHO)-C-t, PhCHO, Me2CO, (CH2)(5)CO and CO2] at -78 degrees C leads, after hydrolysis with water to functionalised alcohols 3, ent-3, 6 and 9. Monoprotected diols 6d and 9d give enantiomerically pure 1,2,5-triols 10 and ent-10 or spirohydroxyethers 11 and ent-11 under acidic conditions in methanol in almost quantitative yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00274-7
• 作为产物：
  描述：

  (-)-薄荷酮 、 dimethylsulfoxonium methylide 以 叔丁醇 为溶剂， 反应 72.0h， 以45%的产率得到(4R,5S,8R)-5-isopropyl-8-methyl-1-oxaspiro[3.5]nonane
  参考文献：
  名称：

  Enantiomerically pure γ-oxidofunctionalised organolithium compounds from chiral oxetanes

  摘要：

  The reductive opening of chiral oxetanes 1, ent-1, 4 and 7 with lithium powder and a catalytic amount of DTBB (5 mol%) in THF at 0 degrees C or -20 degrees C, followed by treatment with different electrophiles [H2O, D2O, (BuCHO)-C-t, PhCHO, Me2CO, (CH2)(5)CO and CO2] at -78 degrees C leads, after hydrolysis with water to functionalised alcohols 3, ent-3, 6 and 9. Monoprotected diols 6d and 9d give enantiomerically pure 1,2,5-triols 10 and ent-10 or spirohydroxyethers 11 and ent-11 under acidic conditions in methanol in almost quantitative yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00274-7

文献信息

• Enantiomerically pure γ-oxidofunctionalised organolithium compounds from chiral oxetanes
  作者：Abderrazak Bachki、Larry R Falvello、Francisco Foubelo、Miguel Yus

  DOI：10.1016/s0957-4166(97)00274-7

  日期：1997.8

  The reductive opening of chiral oxetanes 1, ent-1, 4 and 7 with lithium powder and a catalytic amount of DTBB (5 mol%) in THF at 0 degrees C or -20 degrees C, followed by treatment with different electrophiles [H2O, D2O, (BuCHO)-C-t, PhCHO, Me2CO, (CH2)(5)CO and CO2] at -78 degrees C leads, after hydrolysis with water to functionalised alcohols 3, ent-3, 6 and 9. Monoprotected diols 6d and 9d give enantiomerically pure 1,2,5-triols 10 and ent-10 or spirohydroxyethers 11 and ent-11 under acidic conditions in methanol in almost quantitative yield. (C) 1997 Elsevier Science Ltd.