(RS)-3-hydroxy-1-oxa-2,7-diazaspiro<4.5>dec-2-ene | 138163-06-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (RS)-3-hydroxy-1-oxa-2,7-diazaspiro<4.5>dec-2-ene
• 英文别名: 1-Oxa-2,7-diazaspiro[4.5]decan-3-one；1-oxa-2,9-diazaspiro[4.5]decan-3-one
• CAS: 138163-06-1
• 化学式: C₇H₁₂N₂O₂
• 分子量: 156.184
• InChiKey: IVOVAQHBLXGKPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-哌啶羧酸,3-亚甲基-,苯基甲基酯 在 palladium on activated charcoal 正丁基锂 、 氢气 、 sodium carbonate 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 39.33h， 生成 (RS)-3-hydroxy-1-oxa-2,7-diazaspiro<4.5>dec-2-ene
  参考文献：
  名称：

  Analogues of the low-efficacy partial GABAA agonist 4-PIOL. Syntheses and in vitro pharmacological studies

  摘要：

  4-PIOL (3-hydroxy-5-(4-piperidyl)isoxazole) is a low-efficacy GABA(A) agonist showing a dominating GABA(A) antagonist profile. Three dihydro analogues of 4-PIOL were synthesized, including (RS)-3-hydroxy-5-(4-piperidyl)-2-isoxazoline (1). The synthesis of 1 was based on a regioselective 1,3-dipolar cyclo-addition reaction between 1-benzyloxycarbonyl-4-vinylpiperidine (7) and bromonitrile oxide, prepared in situ from dibromoformoxime. Furthermore, the spiro analogues of 1 3-hydroxy-1-oxa-2,8-diazaspiro[4.5]dec-2-ene (2) and (RS)-3-hydroxy-1-oxa-2,7-diazaspiro[4.5]dec-2-ene (3) were were synthesized regiospecifically via cycloaddition of bromonitrile oxide to the N-benzyloxycarbonyl-protected forms of 4-methylenepiperidine (11) and 3-methylenepiperidine (15), respectively. In contrast to 4-PIOL, none of the new compounds 1-3 showed detectable effects on the binding of H-3-GABA(A) or the subunit-selective GABA(A) agonist, H-3-THIP, to GABA(A) receptor sites, and they did not significantly affect the muscimol-stimulated binding of H-3-diazepam to the benzodiazepine site of the GABA(A) receptor complex.

  DOI：

  10.1016/0223-5234(91)90198-v