2-(bicyclo<2.2.1>hept-2-yl)-1,3-benzodioxole | 80083-51-8

• 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: 2-(bicyclo<2.2.1>hept-2-yl)-1,3-benzodioxole
• 英文别名: Spiro[1,3-benzodioxole-2,2'-bicyclo[2.2.1]heptane]
• CAS: 80083-51-8
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: NJNXUJQUDNXWKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(bicyclo<2.2.1>hept-2-yl)-1,3-benzodioxole 在 lithium aluminium tetrahydride 、 三氯化铝 、 溴 、 叔丁基锂 、 potassium carbonate 作用下， 以 乙醚 、 乙醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 89.5h， 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 、 邻苯二酚 在 3 A molecular sieve 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以85%的产率得到2-(bicyclo<2.2.1>hept-2-yl)-1,3-benzodioxole
  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

• Diallylation of 2,2-dialkylbenzodioxoles from TiCl4-mediated allylsilane reaction
  作者：Nicolas Galy、Delphine Moraleda、Maurice Santelli

  DOI：10.1016/j.tetlet.2009.07.033

  日期：2009.9

  Reaction of aliphatic ketones with catechol afforded 2,2-dialkylbenzodioxoles. Treatment of these benzodioxoles with allyltrimethylsilane in the presence of titanium tetrachloride led to 4,4-dialkylhepta-1,6-dienes resulting from a diallylation process. Ring-closing metathesis gave rise to 4,4-dialkylcyclopentenes. (C) 2009 Elsevier Ltd. All rights reserved.