7-异丙基-5,6-二甲氧基-1,1-二甲基-1,2,3,4,9,10-六氢菲-9-羧酸 | 182306-50-9

• 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
• 中文名称: 7-异丙基-5,6-二甲氧基-1,1-二甲基-1,2,3,4,9,10-六氢菲-9-羧酸
• 英文名称: 5,6-dimethoxy-1,1-dimethyl-7-propan-2-yl-3,4,9,10-tetrahydro-2H-phenanthrene-9-carboxylic acid
• CAS: 182306-50-9
• 化学式: C₂₂H₃₀O₄
• 分子量: 358.478
• InChiKey: GCUWPQSUUWMMAD-UHFFFAOYSA-N

物化性质

• 沸点：
  512.7±50.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-异丙基-5,6-二甲氧基-1,1-二甲基-1,2,3,4,9,10-六氢菲-9-羧酸 在 三溴化硼 作用下， 以 氘代氯仿 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 次丹参醌
  参考文献：
  名称：

  Rearrangement of methyl 11,12-di-O-methyl-6,7-didehydrocarnosate in basic medium. Easy hemisynthesis of miltirone

  摘要：

  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.

  DOI：

  10.1039/p19960002207
• 作为产物：
  描述：

  11,12-dimethoxy-abieta-6,8,11,13-tetraen-20-oic acid methyl ester 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 11,12-Dimethoxy-20-nor-abieta-5(10),6,8,11,13-pentaene 、 7-异丙基-5,6-二甲氧基-1,1-二甲基-1,2,3,4,9,10-六氢菲-9-羧酸 、 5,6-dimethoxy-1,1-dimethyl-7-propan-2-yl-3,4-dihydro-2H-phenanthrene-9-carboxylic acid 、 (4aR,10aS)-5,6-dimethoxy-1,1-dimethyl-7-propan-2-yl-2,3,4,10a-tetrahydrophenanthrene-4a-carboxylic acid
  参考文献：
  名称：

  Rearrangement of methyl 11,12-di-O-methyl-6,7-didehydrocarnosate in basic medium. Easy hemisynthesis of miltirone

  摘要：

  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.

  DOI：

  10.1039/p19960002207

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.