3a-Methyl-3,3a-dihydro-2H-phenalene-1,6-dione | 150931-89-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3a-Methyl-3,3a-dihydro-2H-phenalene-1,6-dione
• CAS: 150931-89-8
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: UBYYTPGQVRVJGK-UHFFFAOYSA-N

物化性质

• 沸点：
  389.9±42.0 °C(predicted)
• 密度：
  1.256±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4,7-dimethoxy-1,3-dihydrobenzo[c]thiophene 2,2-dioxide 、 3a-Methyl-3,3a-dihydro-2H-phenalene-1,6-dione 在 2,6-二叔丁基-4-甲基苯酚 萘烷 作用下， 反应 20.0h， 以87%的产率得到9,12-Dimethoxy-13b-methyl-1,7a,8,13,13a,13b-hexahydro-2H-benzo[de]naphthacene-3,7-dione
  参考文献：
  名称：

  Protein tyrosine kinase inhibitory properties of planar polycyclics obtained from the marine sponge Xestospongia cf. carbonaria and from total synthesis

  摘要：

  Nine related polycyclic quinones and hydroquinones of the halenaquinone class were isolated from two Indo-Pacific collections of the sponge Xestospongia cf. carbonaria. The halenaquinone family appears not to be of polyketide origin but can be biogenetically derived by the union of a sesquiterpene and a quinone. Four new metabolites were characterized including tetrahydrohalenaquinone B (8a), 14-methoxyhalenaquinone (9), xestoquinolide A (10), and xestoquinolide B (11). These were accompanied by five known compounds, halenaquinone (3), halenaquinol (4), halenaquinol sulfate (5), xestoquinone (6), and tetrahydrohalenaquinone A (7a). The new structures were established from 2D NMR data, and the absolute stereochemistry of the chiral centers in 7 and 8 was determined by the formation of 7b and 7c, the bis esters of O-methylmandelic acid. A series of polycyclic models of natural products 3 and 6 were synthesized and included 16-23. The more complex members of this group were assembled via a 4 + 2 cycloaddition between an o-quinodimethane and a functionalized enone. The marine natural products plus two known fungal metabolites, viridin (13) and wortmannin (14), along with halenaquinone synthetic model compounds, were each tested for their ability to inhibit the activity of pp60v-src protein tyrosine kinase (PTK). Halenaquinone and 14-methoxyhalenaquinone were the most potent with IC50 values <10 muM. The other compounds were either less potent or inactive, and a rationalization for this SAR (structure activity relationship) pattern is presented.

  DOI：

  10.1021/jo00070a023
• 作为产物：
  描述：

  3a-Methyl-2,3,3a,4,5,6-hexahydro-phenalen-1-on 在 2,4,6-三甲基吡啶 、 Celite 、 溴 、 pyridinium chlorochromate 作用下， 以 乙醚 、 苯 为溶剂， 反应 1.5h， 生成 3a-Methyl-3,3a-dihydro-2H-phenalene-1,6-dione
  参考文献：
  名称：

  Protein tyrosine kinase inhibitory properties of planar polycyclics obtained from the marine sponge Xestospongia cf. carbonaria and from total synthesis

  摘要：

  Nine related polycyclic quinones and hydroquinones of the halenaquinone class were isolated from two Indo-Pacific collections of the sponge Xestospongia cf. carbonaria. The halenaquinone family appears not to be of polyketide origin but can be biogenetically derived by the union of a sesquiterpene and a quinone. Four new metabolites were characterized including tetrahydrohalenaquinone B (8a), 14-methoxyhalenaquinone (9), xestoquinolide A (10), and xestoquinolide B (11). These were accompanied by five known compounds, halenaquinone (3), halenaquinol (4), halenaquinol sulfate (5), xestoquinone (6), and tetrahydrohalenaquinone A (7a). The new structures were established from 2D NMR data, and the absolute stereochemistry of the chiral centers in 7 and 8 was determined by the formation of 7b and 7c, the bis esters of O-methylmandelic acid. A series of polycyclic models of natural products 3 and 6 were synthesized and included 16-23. The more complex members of this group were assembled via a 4 + 2 cycloaddition between an o-quinodimethane and a functionalized enone. The marine natural products plus two known fungal metabolites, viridin (13) and wortmannin (14), along with halenaquinone synthetic model compounds, were each tested for their ability to inhibit the activity of pp60v-src protein tyrosine kinase (PTK). Halenaquinone and 14-methoxyhalenaquinone were the most potent with IC50 values <10 muM. The other compounds were either less potent or inactive, and a rationalization for this SAR (structure activity relationship) pattern is presented.

  DOI：

  10.1021/jo00070a023