3β,15-diacetoxy-7-oxo-8-labdene | 114360-02-0

• 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: 3β,15-diacetoxy-7-oxo-8-labdene
• 英文别名: [(3S)-5-[(4aR,6S,8aS)-6-acetyloxy-2,5,5,8a-tetramethyl-3-oxo-4a,6,7,8-tetrahydro-4H-naphthalen-1-yl]-3-methylpentyl] acetate
• CAS: 114360-02-0
• 化学式: C₂₄H₃₈O₅
• 分子量: 406.563
• InChiKey: MINQQBSSSOGTOB-BLVZXNIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3β,15-diacetoxy-7-oxo-8-labdene 在 selenium(IV) oxide 、 溶剂黄146 、 锌 作用下， 以 叔丁醇 为溶剂， 反应 31.0h， 生成 3β,15-diacetoxy-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 吡啶 、 sodium chromate(VI) 、 碘 、 sodium acetate 、 乙酸酐 作用下， 以 溶剂黄146 、 苯 为溶剂， 反应 119.0h， 生成 3β,15-diacetoxy-7-oxo-8-labdene
  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

• URONES, JULIO G.;MARCOS, ISIDRO SANCHEZ;BARCALA, PILAR BASABE;GARRIDO, NA+, PHYTOCHEMISTRY, 27,(1988) N 2, 501-504
  作者：URONES, JULIO G.、MARCOS, ISIDRO SANCHEZ、BARCALA, PILAR BASABE、GARRIDO, NA+

  DOI：——

  日期：——
• Diterpenoids of Halimium viscosum
  作者：Julio G. Urones、Isidro Sanchez Marcos、Pilar Basabe Barcala、Narciso Martin Garrido

  DOI：10.1016/0031-9422(88)83130-3

  日期：1988.1
• 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.