7-oxo-5,8-labdene-3β,15-diol dimethylether | 152451-42-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-oxo-5,8-labdene-3β,15-diol dimethylether
• 英文别名: (4aR,7S)-7-methoxy-4-[(3S)-5-methoxy-3-methylpentyl]-3,4a,8,8-tetramethyl-6,7-dihydro-5H-naphthalen-2-one
• CAS: 152451-42-8
• 化学式: C₂₂H₃₆O₃
• 分子量: 348.526
• InChiKey: ZPFXFODTSVQGBG-GJULWVSJSA-N

物化性质

• 沸点：
  439.7±45.0 °C(predicted)
• 密度：
  0.99±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-oxo-5,8-labdene-3β,15-diol dimethylether 在 溶剂黄146 、 锌 作用下， 反应 5.0h， 以91%的产率得到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：

  8-labdene-3β,15-diol dimethylether 在 selenium(IV) oxide 、 sodium chromate(VI) 、 sodium acetate 、 乙酸酐 、 溶剂黄146 作用下， 以 溶剂黄146 、 叔丁醇 为溶剂， 反应 9.0h， 生成 7-oxo-5,8-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.