1,2-dibenzyloxy-5-(aminomethyl)-6,7,8,9-tetrahydrobenzocyclohepten-5-ol | 160848-98-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,2-dibenzyloxy-5-(aminomethyl)-6,7,8,9-tetrahydrobenzocyclohepten-5-ol
• 英文别名: 5-(Aminomethyl)-1,2-bis(phenylmethoxy)-6,7,8,9-tetrahydrobenzo[7]annulen-5-ol
• CAS: 160848-98-6
• 化学式: C₂₆H₂₉NO₃
• 分子量: 403.521
• InChiKey: KEIMVHLCACDUTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丙酮 、 1,2-dibenzyloxy-5-(aminomethyl)-6,7,8,9-tetrahydrobenzocyclohepten-5-ol 在 palladium on activated charcoal 氢气 作用下， 生成 1,2-dihydroxy-5-<(isopropylamino)methyl>-6,7,8,9-tetrahydrobenzocyclohepten-5-ol
  参考文献：
  名称：

  Conformationally restrained analogs of sympathomimetic catecholamines. Synthesis and adrenergic activity of tetrahydrobenzocycloheptene derivatives

  摘要：

  The tetrahydrobenzocycloheptene analogs 7-10 of norepinephrine (NE, 1) and isoproterenol (ISO, 2) were synthesized and tested for their alpha- and beta-adrenergic properties by means of functional tests on isolated preparations. The conformational profile of 7 was studied by means of theoretical calculations. The results of the pharmacological tests showed that, in general, the cyclization of NE (1) and ISO (2) to their semirigid analogs 7-10 leads to a marked reduction or even to the disappearance of the adrenergic activity of the corresponding open-chain compounds 1 and 2. Possible rationalizations of the differences in alpha(2)-adrenergic activity shown by the benzocycloheptene derivative 7 and the corresponding previously studied tetrahydronaphthalene derivative 3 are suggested on the basis of a comparison of their stereostructures in the preferred conformations.

  DOI：

  10.1016/0223-5234(94)90133-3
• 作为产物：
  描述：

  1,2-Bis-benzyloxy-5-trimethylsilanyloxy-6,7,8,9-tetrahydro-5H-benzocycloheptene-5-carbonitrile 在 lithium aluminium tetrahydride 作用下， 以 乙醚 、 苯 为溶剂， 反应 2.0h， 生成 1,2-dibenzyloxy-5-(aminomethyl)-6,7,8,9-tetrahydrobenzocyclohepten-5-ol
  参考文献：
  名称：

  Conformationally restrained analogs of sympathomimetic catecholamines. Synthesis and adrenergic activity of tetrahydrobenzocycloheptene derivatives

  摘要：

  The tetrahydrobenzocycloheptene analogs 7-10 of norepinephrine (NE, 1) and isoproterenol (ISO, 2) were synthesized and tested for their alpha- and beta-adrenergic properties by means of functional tests on isolated preparations. The conformational profile of 7 was studied by means of theoretical calculations. The results of the pharmacological tests showed that, in general, the cyclization of NE (1) and ISO (2) to their semirigid analogs 7-10 leads to a marked reduction or even to the disappearance of the adrenergic activity of the corresponding open-chain compounds 1 and 2. Possible rationalizations of the differences in alpha(2)-adrenergic activity shown by the benzocycloheptene derivative 7 and the corresponding previously studied tetrahydronaphthalene derivative 3 are suggested on the basis of a comparison of their stereostructures in the preferred conformations.

  DOI：

  10.1016/0223-5234(94)90133-3