4a-Methyl-5-vinyl-7,8-dihydro-4aH-naphthalen-2-one | 152769-53-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4a-Methyl-5-vinyl-7,8-dihydro-4aH-naphthalen-2-one
• CAS: 152769-53-4
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: VAWZRWJSQKPADS-UHFFFAOYSA-N

物化性质

• 沸点：
  324.4±42.0 °C(predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  水合茚三酮 、 4a-Methyl-5-vinyl-7,8-dihydro-4aH-naphthalen-2-one 以 甲苯 为溶剂， 反应 0.17h， 以49%的产率得到5',6',8',9',10',10a'-hexahydro-10a'-methylspiro<2H-indene-2,3'<3H>-naphtho<2,1-b>pyran-1,3,8'(6a'H)-trione>
  参考文献：
  名称：

  Non-steroidal glucocorticoid-like substances: receptor binding and in vivo activity

  摘要：

  Compounds of general structure I, prepared by a Diels-Alder reaction with diene 3, are relatives of the known potent glucocorticoid II but possess a markedly modified C- and D-ring environment. Despite these structural changes, 4, 5, 9, 10, 12a, 13, and 14 bound to the glucocorticoid receptor with an affinity which approximated that of the reference standard, 6-alpha-methylprednisolone. Four of these compounds not only exhibited antiinflammatory activity in the alpha-tocopherol pouch test but also exhibited marked adrenal suppression and other typical glucocorticoid properties at doses in the same range as the effective antiinflammatory doses.

  DOI：

  10.1021/jm00074a008
• 作为产物：
  描述：

  5-ethenyl-4,4a,7,8-tetrahydro-4a-methyl-2(3H)-naphthalenone 在 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 41.0h， 生成 4a-Methyl-5-vinyl-7,8-dihydro-4aH-naphthalen-2-one
  参考文献：
  名称：

  Non-steroidal glucocorticoid-like substances: receptor binding and in vivo activity

  摘要：

  Compounds of general structure I, prepared by a Diels-Alder reaction with diene 3, are relatives of the known potent glucocorticoid II but possess a markedly modified C- and D-ring environment. Despite these structural changes, 4, 5, 9, 10, 12a, 13, and 14 bound to the glucocorticoid receptor with an affinity which approximated that of the reference standard, 6-alpha-methylprednisolone. Four of these compounds not only exhibited antiinflammatory activity in the alpha-tocopherol pouch test but also exhibited marked adrenal suppression and other typical glucocorticoid properties at doses in the same range as the effective antiinflammatory doses.

  DOI：

  10.1021/jm00074a008