(R)-4'-benzyl-3,4-dihydroxytolazoline | 85612-45-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (R)-4'-benzyl-3,4-dihydroxytolazoline
• 英文别名: 4-[[(4R)-4-benzyl-4,5-dihydro-1H-imidazol-2-yl]methyl]benzene-1,2-diol;hydrochloride
• CAS: 85612-45-9
• 化学式: C₁₇H₁₈N₂O₂*ClH
• 分子量: 318.803
• InChiKey: ZSFFNOJZHIQTLN-PFEQFJNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.66
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  66.5
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (R)-4-Benzyl-2-(3,4-bis-benzyloxy-benzyl)-4,5-dihydro-1H-imidazole; hydrochloride 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以89%的产率得到(R)-4'-benzyl-3,4-dihydroxytolazoline
  参考文献：
  名称：

  Optically active catecholimidazolines: a study of steric interactions at .alpha.-adrenoreceptors

  摘要：

  The optical isomers and deoxy form of 2-(3,4, alpha-trihydroxybenzyl)imidazoline hydrochloride were examined for their alpha-adrenergic activity on rat aorta. The rank order of stimulant activity was deoxy (2) congruent to (R)-(-)-1 greater than (S)-(+)-1. This is in contrast to catecholamines in which the order of activity is (R)-(-)-epinephrine greater than (S)-(+)-epinephrine = epinine (deoxyepinephrine). The relative order of potency for the isomers of 2-(3,4, alpha-trihydroxybenzyl)imidazoline is different than that predicted by the Easson--Stedman theory for stereoisomers of catecholamines. Also, substitution of the deoxy compound 2 with substituents, methyl or benzyl, in the 4-position lowers the alpha-adrenergic agonist activity, and differences observed between optical isomers were small.

  DOI：

  10.1021/jm00361a005