3-cyano-3-(1-piperidinyl)-3,4,5,6-tetrahydro-2H-thiopyran | 112799-07-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: 3-cyano-3-(1-piperidinyl)-3,4,5,6-tetrahydro-2H-thiopyran
• 英文别名: 3-Piperidino-5,6-dihydro-2H-thiopyran-3(4H)-carbonitril；3-piperidinotetrahydro-2H-thiopyran-3-carbonitrile；Thioxane-3-carbonitrile, 3-piperidyl-；3-piperidin-1-ylthiane-3-carbonitrile
• CAS: 112799-07-2
• 化学式: C₁₁H₁₈N₂S
• 分子量: 210.343
• InChiKey: IMYZVFFDFAAPLC-UHFFFAOYSA-N

物化性质

• 熔点：
  96 °C
• 沸点：
  354.2±42.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  magnesium,2H-thiophen-2-ide,bromide 、 3-cyano-3-(1-piperidinyl)-3,4,5,6-tetrahydro-2H-thiopyran 以 乙醚 为溶剂， 反应 20.0h， 以83%的产率得到1-<3-(2-thienyl)-3,4,5,6-tetrahydro-2H-thiopyran-3-yl>piperidine
  参考文献：
  名称：

  The search for TCP analogues binding to the low affinity PCP receptor sites in the rat cerebellum

  摘要：

  With the aim of obtaining selective ligands of the low affinity binding sites of [H-3]-1-[1-(2-thienyl) cyclohexyl] piperidine ([H-3]TCP) in the rat cerebellum, oxygen and sulfur atoms were introduced in the TCP structure and derivatives to obtain analogues with a lowered lipophilicity. These compounds, and others already obtained, were assayed comparatively to determine their affinities for three sites labeled with [H-3]TCP: one in the forebrain, the originally described PCP receptor, and two in the rat cerebellum. Lowering the Lipophilicity and modifying the hetero-aromatic moiety yielded some Ligands with increased affinity for the low affinity sites in the rat cerebellum and decreased affinity for the high affinity sites in the forebrain. Particularly, two compounds displaying both a high affinity and a good selectivity might be valuable tools to elucidate the pharmacology of the low affinity PCP sites labeled with [H-3]TCP in the rat cerebellum. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80046-4
• 作为产物：
  描述：

  二氢-2H-硫代吡喃-3(4h)-酮 、 哌啶 以92%的产率得到
  参考文献：
  名称：

  EIDEN F.; SCHMIDT M.; BUCHBORN H., ARCH. PHARM., 320,(1987) N 4, 348-361

  摘要：

  DOI：

文献信息

• Synthese und pharmakologische Prüfung ZNS-wirksamer Phenyl-tetrahydropyrane und -thiopyrane: Oxa- und Thia-phencyclidine
  作者：Fritz Eiden、Michael Schmidt、Helga Buchborn

  DOI：10.1002/ardp.19873200413

  日期：——

  Aus den Pyranonen 2 und 14 sowie den Thiopyranonen 3 und 15 wurden Phencyclidin‐oxa‐ und ‐thiaanaloge dargestellt. An Mäusen zeigten die Pyranderivate ein günstigeres Verhältnis von Analgesie und Erregung als Phencyclidin. Während die analgetischen Eigenschaften der Enantiomere (+)‐20b und (−)‐20b gleich waren, ließ sich eine erregende Wirkung bei (+)‐20b nicht mehr feststellen. Die Thiopyranderivate

  由吡喃酮 2 和 14 以及吡喃酮 3 和 15 制备苯环利定氧杂和硫杂类似物。在小鼠中，吡喃衍生物显示出比苯环利定更有利的镇痛和唤醒比率。虽然对映异构体 (+) - 20b 和 (-) - 20b 的镇痛特性相同，但 (+) - 20b 不再能确定令人兴奋的效果。噻喃衍生物无效。
• Substituted 1-(2-Thienyl)cyclohexylamines and Related Compounds as Potential NMDA Antagonists
  作者：Karel Šindelář、Karel Dobrovský、Ivan Krejčí、Zdeněk Polívka

  DOI：10.1135/cccc19950894

  日期：——

  Reactions of bisulfite addition compounds prepared in situ from cyclohexanone or 3,4,5,6-tetrahydro-2H-thiopyran-3-one with potassium cyanide and corresponding amines resulted with high yields in amino nitriles type of V and VI. These compounds were subjected to reactions with 2-thienylmagnesium bromide and in the case of the amino nitriles Vc and Vf with 5-bromo-2-thienylmagnesium bromide. Only in the case of compound Vf, a by-product X was isolated in addition to the desired 1-[1-(5-bromo-2-thienyl)-1-cyclohexyl]piperidine (VIIf). Compound VIIf was used for the synthesis of the carboxylic acid XI. The compounds prepared were tested by some methods of biochemical and behavioural pharmacology.

  通过从环己酮或3,4,5,6-四氢-2H-硫吡喃-3-酮与氰化钾和相应胺反应制备的亚硫酸氢盐加合物，在高收率下生成了氨基腈类的化合物V和VI。这些化合物经过与2-噻吩基镁溴化物的反应，以及在氨基腈Vc和Vf的情况下与5-溴-2-噻吩基镁溴化物的反应。只有在化合物Vf的情况下，除了所需的1-[1-(5-溴-2-噻吩基)-1-环己基]哌啶（VIIf）之外，还分离出了副产物X。化合物VIIf被用于合成羧酸XI。制备的化合物经过一些生化和行为药理学方法进行了测试。