4aβ-Methyl-3,4,4a,7,8,8a-hexahydronaphthalin-2(1)-on | 18680-70-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4aβ-Methyl-3,4,4a,7,8,8a-hexahydronaphthalin-2(1)-on
• 英文别名: (4aR,8aR)-4a-methyl-1,3,4,7,8,8a-hexahydronaphthalen-2-one
• CAS: 18680-70-1；22489-59-4；80800-81-3；150931-94-5
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: AZIVURUBLCCCKL-MWLCHTKSSA-N

物化性质

• 沸点：
  243.5±39.0 °C(Predicted)
• 密度：
  1.007±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4aβ-Methyl-3,4,4a,7,8,8a-hexahydronaphthalin-2(1)-on 在 2,6-二叔丁基-4-甲基苯酚 3,5-二甲基吡唑 、 chromium(VI) oxide 作用下， 以 二氯甲烷 、 萘烷 为溶剂， 反应 8.0h， 生成
  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：

  (4aS*,8aS*)-8a-methyloctahydro-2H-spiro[naphthalene-1,2'-[1,3]dioxolan]-6-ol 在 草酰氯 、 甲基锂 、 对甲苯磺酸 、 二甲基亚砜 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 5.5h， 生成 4aβ-Methyl-3,4,4a,7,8,8a-hexahydronaphthalin-2(1)-on
  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

文献信息

• Synthesis of stereoisomeric 9a-methylhydrodicyclopenta[a,d]cyclooctan-1-ones related to the ophiobolins and ceroplastins via annelative ring expansion of hydrindene precursors
  作者：Robert M. Coates、Jack W. Muskopf、Peter A. Senter

  DOI：10.1021/jo00219a022

  日期：1985.9
• Synthesis of hydroazulenes by solvolytic rearrangement of 9-methyl-1-declyl tosylates
  作者：Clayton H. Heathcock、Ronald Ratcliffe、James Van

  DOI：10.1021/jo00976a029

  日期：1972.6