(6RS,11RS)-2-benzyl-11-hydroxymethyl-2-azaspiro<5.5>undecane | 140886-85-7

• 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: (6RS,11RS)-2-benzyl-11-hydroxymethyl-2-azaspiro<5.5>undecane
• 英文别名: (6RS, 7RS)-N-benzyl-7-hydroxymethyl-2-azaspiro<5.5>undecane
• CAS: 140886-85-7
• 化学式: C₁₈H₂₇NO
• 分子量: 273.418
• InChiKey: VVKAHEDOWHCMMZ-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  23.47
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (6RS,11RS)-2-benzyl-11-hydroxymethyl-2-azaspiro<5.5>undecane 在 chromium(VI) oxide 、 硫酸 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 生成 (6S,7S)-2-Benzyl-2-aza-spiro[5.5]undecane-7-carboxylic acid
  参考文献：
  名称：

  Synthesis and biochemical studies of spirocyclic amino acids. II. Activity of 2-azaspiro[5.5]undecane-7-carboxylates as GABA-uptake inhibitors

  摘要：

  Novel GABA analogous spirocyclic amino acids were prepared and investigated for interaction with GABA-A and GABA-B receptors as well as the GABA uptake system. Starting from known bromopropyl lactones and arylalkylamines, spirocyclic hydroxyalkyl lactams were obtained, which were reduced by LiAlH4 to yield spirocyclic hydroxymethyl piperidines. Oxidation by Jones' reagent followed by subsequent esterification gave the title compounds which represent conformationally restricted analogues of GABA. Whereas the new spirocyclic amino acids showed no activity at GABA receptors they proved to be active as GABA uptake inhibitors. An examination of the relationship between structure and GABA uptake inhibition;revealed a strong dependence of activity on the length of the aikyl chain in N-arylalkyl substituents.

  DOI：

  10.1016/0223-5234(96)88288-2
• 作为产物：
  描述：

  hexahydro-isobenzo[c]furan-1-one 在 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 35.0h， 生成 (6RS,11RS)-2-benzyl-11-hydroxymethyl-2-azaspiro<5.5>undecane
  参考文献：
  名称：

  Dostal, Claudia; Lauritz, Silvia; Urban, Ernst, Heterocycles, 1992, vol. 34, # 1, p. 135 - 148

  摘要：

  DOI：