11,12-Dimethoxy-20-nor-abieta-5(10),6,8,11,13-pentaene | 182306-54-3

• 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: 11,12-Dimethoxy-20-nor-abieta-5(10),6,8,11,13-pentaene
• 英文别名: 5,6-dimethoxy-1,1-dimethyl-7-propan-2-yl-3,4-dihydro-2H-phenanthrene
• CAS: 182306-54-3
• 化学式: C₂₁H₂₈O₂
• 分子量: 312.452
• InChiKey: PFXZWOPFLXIDNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  429.3±45.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  11,12-Dimethoxy-20-nor-abieta-5(10),6,8,11,13-pentaene 在 ammonium cerium(IV) nitrate 、 三溴化硼 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.0h， 生成 次丹参醌
  参考文献：
  名称：

  Use of Conjugated Dienones in Cyclialkylations:  Total Syntheses of Arucadiol, 1,2-Didehydromiltirone, (±)-Hinokione, (±)-Nimbidiol, Sageone, and Miltirone

  摘要：

  Functionalized hydrophenanthrenes can be prepared using a cyclialkylation-based strategy. These annulations are highly dependent on the directing effects of the arene substitutents and on conformational considerations. The utility of this methodology was featured in the syntheses of six diterpenoids.

  DOI：

  10.1021/jo970570q
• 作为产物：
  描述：

  5,6-Dimethoxy-1,1-dimethyl-7-propan-2-yl-2,3,9,10-tetrahydrophenanthren-4-one 在 盐酸 、 溴甲酚绿 、 sodium cyanoborohydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 环丁砜 、 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 32.0h， 生成 11,12-Dimethoxy-20-nor-abieta-5(10),6,8,11,13-pentaene
  参考文献：
  名称：

  Use of Conjugated Dienones in Cyclialkylations:  Total Syntheses of Arucadiol, 1,2-Didehydromiltirone, (±)-Hinokione, (±)-Nimbidiol, Sageone, and Miltirone

  摘要：

  Functionalized hydrophenanthrenes can be prepared using a cyclialkylation-based strategy. These annulations are highly dependent on the directing effects of the arene substitutents and on conformational considerations. The utility of this methodology was featured in the syntheses of six diterpenoids.

  DOI：

  10.1021/jo970570q

文献信息

• Rearrangement of methyl 11,12-di-O-methyl-6,7-didehydrocarnosate in basic medium. Easy hemisynthesis of miltirone
  作者：Javier G. Luis、Lucía S. Andrés、Winston Q. Fletcher、El Hassane Lahlou、Aurea Perales

  DOI：10.1039/p19960002207

  日期：——

  Methyl 11,12-di-O-methyl-6,7-didehydrocarnosate 3, obtained from the abundant natural product carnosol 1, undergoes an interesting rearrangement when treated with potassium tert-butoxide in dimethyl sulfoxide to give 11,12-dimethoxy-20(10-->7)abeo-abieta-5(10),8,11,13-tetraen-20- oic acid 4, in which an additional double bond is formed between C-5 and C-10 and the carboxylic acid group has migrated from C-10 to C-7, Deprotection of the two methyl ether moieties in 4 with BBr3 allows spontaneous air oxidation and decarboxylation of the catechol derivative to give the potent benzodiazepine agonist miltirone 10. The structure of 6 has been unequivocally elucidated by X-ray diffraction analysis and indirect chemical correlation between 4 and 6 has been established.
• Use of Conjugated Dienones in Cyclialkylations:  Total Syntheses of Arucadiol, 1,2-Didehydromiltirone, (±)-Hinokione, (±)-Nimbidiol, Sageone, and Miltirone
  作者：George Majetich、Shuang Liu、Jing Fang、David Siesel、Yong Zhang

  DOI：10.1021/jo970570q

  日期：1997.10.1

  Functionalized hydrophenanthrenes can be prepared using a cyclialkylation-based strategy. These annulations are highly dependent on the directing effects of the arene substitutents and on conformational considerations. The utility of this methodology was featured in the syntheses of six diterpenoids.