4-bromo-2-(endo-bicyclo<2.2.1>hept-2-yloxy)-1-methoxybenzene | 115898-55-0

• 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: 4-bromo-2-(endo-bicyclo<2.2.1>hept-2-yloxy)-1-methoxybenzene
• 英文别名: (1R,2S,4S)-2-(5-bromo-2-methoxyphenoxy)bicyclo[2.2.1]heptane
• CAS: 115898-55-0；131408-28-1
• 化学式: C₁₄H₁₇BrO₂
• 分子量: 297.192
• InChiKey: XSYCUGZCWCNNAJ-CWSCBRNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  4-bromo-2-(endo-bicyclo<2.2.1>hept-2-yloxy)-1-methoxybenzene 在 叔丁基锂 作用下， 以 乙醇 、 水 为溶剂， 反应 74.0h， 生成 2-(3-(((1S,4R)-bicyclo[2.2.1]heptan-2-yl)oxy)-4-methoxyphenyl)-2-(methylamino)acetonitrile
  参考文献：
  名称：

  Calcium-independent phosphodiesterase inhibitors as putative antidepressants: [3-(bicycloalkyloxy)-4-methoxyphenyl-2-imidazolidinones

  摘要：

  The synthesis and biological properties of a novel series of selective calcium-independent phosphodiesterase inhibitors are described. These compounds also inhibit the specific binding of [H-3]rolipram to rat brain membranes and exhibit efficacy in preclinical models of antidepressant activity in mice, such as reducing immobility in the forced-swim test and reversing reserpine-induced hypothermia. Imidazolidinones 4 and 16 were found to be the most potent compounds studied.

  DOI：

  10.1021/jm00105a045
• 作为产物：
  描述：

  降樟脑 在 lithium aluminium tetrahydride 、 三氯化铝 、 3 A molecular sieve 、 溴 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 乙醚 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 30.5h， 生成 4-bromo-2-(endo-bicyclo<2.2.1>hept-2-yloxy)-1-methoxybenzene
  参考文献：
  名称：

  Calcium-independent phosphodiesterase inhibitors as putative antidepressants: [3-(bicycloalkyloxy)-4-methoxyphenyl-2-imidazolidinones

  摘要：

  The synthesis and biological properties of a novel series of selective calcium-independent phosphodiesterase inhibitors are described. These compounds also inhibit the specific binding of [H-3]rolipram to rat brain membranes and exhibit efficacy in preclinical models of antidepressant activity in mice, such as reducing immobility in the forced-swim test and reversing reserpine-induced hypothermia. Imidazolidinones 4 and 16 were found to be the most potent compounds studied.

  DOI：

  10.1021/jm00105a045

文献信息

• Calcium-independent phosphodiesterase inhibitors as putative antidepressants: [3-(bicycloalkyloxy)-4-methoxyphenyl-2-imidazolidinones
  作者：Nicholas A. Saccomano、Frederic J. Vinick、B. Kenneth Koe、Jann A. Nielsen、William M. Whalen、Morgan Meltz、Douglas Phillips、Peter F. Thadieo、Stanley Jung、Douglas C. Chapin、Lorraine A. Lebel、Lorena L. Russo、David L. Helweg、Jonathan L. Johnson Jr、Jeffery L. Ives、Ian H. Williams

  DOI：10.1021/jm00105a045

  日期：1991.1

  The synthesis and biological properties of a novel series of selective calcium-independent phosphodiesterase inhibitors are described. These compounds also inhibit the specific binding of [H-3]rolipram to rat brain membranes and exhibit efficacy in preclinical models of antidepressant activity in mice, such as reducing immobility in the forced-swim test and reversing reserpine-induced hypothermia. Imidazolidinones 4 and 16 were found to be the most potent compounds studied.