α-(S,S)-1-(2-piperidyl)-1,2-ethanediol hydrochloride | 30162-99-3

• 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: α-(S,S)-1-(2-piperidyl)-1,2-ethanediol hydrochloride
• 英文别名: (4S,6S)-1-(2-piperidyl)-1,2-ethanediol hydrochloride
• CAS: 30162-99-3
• 化学式: C₇H₁₅NO₂*ClH
• 分子量: 181.663
• InChiKey: MSORVUQKYGOBAI-UOERWJHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.49
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  9-芴酮二甲基缩醛 、 α-(S,S)-1-(2-piperidyl)-1,2-ethanediol hydrochloride 在 对甲苯磺酸 作用下， 以 异丙醇 为溶剂， 反应 0.33h， 生成 (4S,6S)-4-(2-piperidyl)spiro[1,3-dioxolane-2,9'-[9H]fluorene]
  参考文献：
  名称：

  Analogs of the dioxolanes dexoxadrol and etoxadrol as potential phencyclidine-like agents. Synthesis and structure activity relationships

  摘要：

  A series of dioxolane analogues based on dexoxadrol ((4S,6S)-2,2-diphenyl-4-(2-piperidyl)-1,3-dioxolane) and etoxadrol ((2S,4S,6S)-2-ethyl-2-phenyl-4-(2-piperidyl)-1,3-dioxolane) were prepared and tested for their ability to displace [H-3]TCP (1-[1-(2-thienyl)cyclohexyl]piperidine) from PCP (1-(1-phenylcyclohexyl)piperidine) binding sites in rat brain tissue homogenates. Qualitative structure-activity relationships within this series were explored through modifications of the three major structural units of dexoxadrol, the piperidine, 1,3-dioxolane, and aromatic rings of the molecule. N-Alkyl derivatives of dexoxadrol were found to be inactive, as were those analogues where the dioxolane ring was modified. Phenyl-substituted etoxadrol analogues were compared to similarly substituted PCP analogues and distinct differences were found in their structure-activity relationships suggesting that the aromatic rings in these two drug classes interact differently with the PCP binding sites. The replacement of the phenyl ring in etoxadrol by either a 2- or 3-thienyl ring led to compounds with affinity comparable to etoxadrol, and the replacement of the ethyl moiety on etoxadrol's dioxolane ring with propyl (7) or isopropyl (8) led to compounds which were more potent than etoxadrol or PCP. The most potent compound was (2S,4S,6S)-2-ethyl-2-(1-chlorophenyl)-4-(2-piperidyl)-1,3-dioxolane (11), where a chlorine moiety was placed in the ortho position in the aromatic ring of etoxadrol. Its potency was comparable with TCP in vitro.

  DOI：

  10.1021/jm00086a001
• 作为产物：
  描述：

  右奥沙屈 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 10.0h， 以100%的产率得到α-(S,S)-1-(2-piperidyl)-1,2-ethanediol hydrochloride
  参考文献：
  名称：

  强大的苯环利定样激动剂艾托沙醇的合成，绝对构型和分子模型研究。

  摘要：

  由（S，S）-1-（2-哌啶基）合成了Etoxadrol（2a），它是2-乙基-2-苯基-4-（2-哌啶基）-1,3-二氧戊环的8种可能的光学异构体之一）-1,2-乙二醇，它是由右旋沙多醇（1a，（S，S）-2,2-二苯基-4-（2-哌啶基）-1,3-二氧戊环）的裂解获得的。通过单晶X射线分析，确定其在生理学上呈苯环类化合​​物的艾托沙醇盐酸盐的绝对构型，在其三个手性中心处分别为2S，4S和6S。还从合成中获得了在C-2中心与依托沙醇一起异构的表艾托沙醇（2b）。这种效力低得多的对映异构体具有2R，4S，6S构型。发现埃托沙醇对苯环利定结合位点的亲和力可与苯环利定本身相当，并且其效价为其差向异构体表哌沙他醇的35倍。制备了三种非对映异构体混合物，它们对苯环利定位点的亲和力低。在对这些化合物的区分刺激特性进行的研究中，发现只有艾托沙特能代替苯环利定刺激。通过使用计算机辅助分子建模技术，已经开

  DOI：

  10.1021/jm00120a004