3-(hydroxymethyl)-1-methyl-1-oxopiperidine | 103003-02-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-(hydroxymethyl)-1-methyl-1-oxopiperidine
• 英文别名: 3-Piperidinemethanol, 1-methyl-, 1-oxide；(1-methyl-1-oxidopiperidin-1-ium-3-yl)methanol
• CAS: 103003-02-7
• 化学式: C₇H₁₅NO₂
• 分子量: 145.202
• InChiKey: PKDMWYQZOGACKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(hydroxymethyl)-1-methyl-1-oxopiperidine 、 (E),(Z)-(6-chloro-11H-dibenzazepin-11-ylidene)acetonitrile 生成 2-[6-[(1-methyl-1-oxidopiperidin-1-ium-3-yl)methoxy]benzo[c][1]benzazepin-11-ylidene]acetonitrile
  参考文献：
  名称：

  Tricyclic epines. Novel (E)- and (Z)-11H-dibenz[b,e]azepines as potential central nervous system agents. Variation of the basic side chain

  摘要：

  The synthesis and pharmacological activity of new (E),(Z)-[6-(alkylamino)-11H-dibenz[b,e]azepin-11- ylidene]acetonitriles 12-45 and (E),(Z)-[6-(aminoalkoxy)-11H-dibenz[b,e]azepin-11-ylidene] acetonitriles 46-51 are described. The introduction of the cyanomethylene group into the 11-position of the 11H-dibenz[b,e]azepine framework has been carried out by a Wittig-Horner reaction under mild conditions. The (E),(Z) isomers were separated by fractional crystallization, assignment being achieved by X-ray analysis. A number of (E),(Z)-[6-(alkylamino)-11H-dibenz-[b,e]azepin-11-ylidene] acetonitriles (12, 14, 16, 20) show potent neuroleptic activity (2-7 times that of clozapine) in animal tests. The screening included tests for sedative and anticholinergic activity in mice, apomorphine and tryptamine antagonism in rats, and muscle-relaxing activity in rabbits. The divergence in the activity profile in the case of the separated (E),(Z) isomers has been observed as an interesting new aspect: the (Z) isomers show a significantly higher sedative and muscle-relaxant activity, whereas the (E) isomers possess a higher anticholinergic efficacy and somewhat greater apomorphine antagonism. Broad changes in the basic side chain were made in order to investigate structure-activity relationships. The important geometrical parameters for the molecules, obtained by X-ray analysis, were compared with the corresponding features in dopamine agonists and antagonists.

  DOI：

  10.1021/jm00160a015