(8R,11S)-8-methyl-3-methylidene-11-propan-2-yl-1,5-dioxaspiro[5.5]undecane | 105857-49-6

• 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: (8R,11S)-8-methyl-3-methylidene-11-propan-2-yl-1,5-dioxaspiro[5.5]undecane
• CAS: 105857-49-6
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: CODHCAKJHNXMKV-YPMHNXCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (8R,11S)-8-methyl-3-methylidene-11-propan-2-yl-1,5-dioxaspiro[5.5]undecane 在 palladium on activated charcoal 氢气 、 四氯化钛 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.75h， 生成 2-[(1R,2S,5R)-1-((R)-3-Hydroxy-2-methyl-propoxy)-2-isopropyl-5-methyl-cyclohexyl]-1-phenyl-ethanone
  参考文献：
  名称：

  Enantioselective functionalization of prochiral diols via chiral spiroketals: preparation of optically pure 2-substituted 1,3-propanediol derivatives and asymmetric synthesis of chroman ring and side chain of .alpha.-tocopherol

  摘要：

  DOI：

  10.1021/ja00236a034
• 作为产物：
  描述：

  (-)-薄荷酮 、 2-methylene-1,3-bis(trimethylsiloxy)propane 在 吡啶 、 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 作用下， 生成 (8R,11S)-8-methyl-3-methylidene-11-propan-2-yl-1,5-dioxaspiro[5.5]undecane
  参考文献：
  名称：

  Enantioselective functionalization of prochiral diols via chiral spiroketals: preparation of optically pure 2-substituted 1,3-propanediol derivatives and asymmetric synthesis of chroman ring and side chain of .alpha.-tocopherol

  摘要：

  DOI：

  10.1021/ja00236a034

文献信息

• A general method for the preparation of enantiomerically pure 2-substituted glycerol derivatives by utilizing l-menthone as a chiral template
  作者：Toshiro Harada、Hiroyuki Nakajima、Takayuki Ohnishi、Masahiro Takeuchi、Akira Oku

  DOI：10.1021/jo00028a057

  日期：1992.1

  A general method for preparation of a variety of enantiomerically pure 2-substituted glycerol derivatives 1 was developed by utilizing l-menthone as a chiral template. Spiroacetals 6 derived formally from 2-substituted 2-(trimethylsiloxy)-1,3-propanediols and l-menthone were prepared with high stereoselectivity (> 95% de) either by Grignard reactions of oxospiroacetal 4 or by epoxidation of methylenespiroacetal 5 followed by ring opening with higher order cuprates. Highly stereoselective ring-cleavage reaction of 6 with acetophenone enol trimethylsilyl ether and TiCl4 followed by protection of the resulting diol 10 and subsequent removal of the chiral auxiliary gave 2-substituted glycerol derivatives of high enantiomeric purity.
• Enantioselective functionalization of prochiral diols via chiral spiroketals: preparation of optically pure 2-substituted 1,3-propanediol derivatives and asymmetric synthesis of chroman ring and side chain of .alpha.-tocopherol
  作者：Toshiro Harada、Toshio Hayashiya、Isao Wada、Naoko Iwaake、Akira Oku

  DOI：10.1021/ja00236a034

  日期：1987.1