8-labdene-3β,15-diol dimethylether | 152451-40-6

• 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: 8-labdene-3β,15-diol dimethylether
• 英文别名: (3S,4aR,8aS)-3-methoxy-8-[(3S)-5-methoxy-3-methylpentyl]-4,4,7,8a-tetramethyl-1,2,3,4a,5,6-hexahydronaphthalene
• CAS: 152451-40-6
• 化学式: C₂₂H₄₀O₂
• 分子量: 336.558
• InChiKey: PUGUHSWGYSJOSG-RAWXMELESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  8-labdene-3β,15-diol dimethylether 在 selenium(IV) oxide 、 sodium chromate(VI) 、 sodium acetate 、 乙酸酐 、 溶剂黄146 、 锌 作用下， 以 溶剂黄146 、 叔丁醇 为溶剂， 反应 14.0h， 生成 3β,15-dimethoxy-20-nor-labda-5,7,9-trien-7-ol
  参考文献：
  名称：

  Chemistry of 7-labden-3β,15-diol (I): homochiral synthesis of fregenedadiol

  摘要：

  7-labden-3beta,15-diol was transformed into its diacetyl or dimethoxy derivatives. By double bond isomerization, allylic oxidation and dehydrogenation the diacetyl derivative was transformed into a dienone that was aromatized with good yield by methyl loss to afford 3beta,15-diacetoxy-20-nor-5,7,9-labdatrien-7-ol. An analog procedure was used to transform the dimethoxy derivative into 3beta,15-dimethoxy-20-nor-5,7,9-labdatrien- 7-ol. The triflate of the latter was transformed by a cross-coupling reaction into fregenedadiol dimethyl ether that was demethylated to afford fregenedadiol.

  DOI：

  10.1016/s0040-4020(01)87192-1
• 作为产物：
  描述：

  7-labden-3β,15-diol 在 碘 、 sodium hydride 作用下， 以 苯 为溶剂， 反应 164.5h， 生成 8-labdene-3β,15-diol dimethylether
  参考文献：
  名称：

  Chemistry of 7-labden-3β,15-diol (I): homochiral synthesis of fregenedadiol

  摘要：

  7-labden-3beta,15-diol was transformed into its diacetyl or dimethoxy derivatives. By double bond isomerization, allylic oxidation and dehydrogenation the diacetyl derivative was transformed into a dienone that was aromatized with good yield by methyl loss to afford 3beta,15-diacetoxy-20-nor-5,7,9-labdatrien-7-ol. An analog procedure was used to transform the dimethoxy derivative into 3beta,15-dimethoxy-20-nor-5,7,9-labdatrien- 7-ol. The triflate of the latter was transformed by a cross-coupling reaction into fregenedadiol dimethyl ether that was demethylated to afford fregenedadiol.

  DOI：

  10.1016/s0040-4020(01)87192-1

文献信息

• Chemistry of 7-labden-3β,15-diol (I): homochiral synthesis of fregenedadiol
  作者：Julio G. Urones、Isidro S. Marcos、Pilar Basabe、Narciso M. Garrido、Asunción Jorge、Rosalina F. Moro、Anna M. Lithgow

  DOI：10.1016/s0040-4020(01)87192-1

  日期：1993.7

  7-labden-3beta,15-diol was transformed into its diacetyl or dimethoxy derivatives. By double bond isomerization, allylic oxidation and dehydrogenation the diacetyl derivative was transformed into a dienone that was aromatized with good yield by methyl loss to afford 3beta,15-diacetoxy-20-nor-5,7,9-labdatrien-7-ol. An analog procedure was used to transform the dimethoxy derivative into 3beta,15-dimethoxy-20-nor-5,7,9-labdatrien- 7-ol. The triflate of the latter was transformed by a cross-coupling reaction into fregenedadiol dimethyl ether that was demethylated to afford fregenedadiol.