(3-methyl-2-oxaadamant-1-yl)amine hydrochloride | 1160239-41-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (3-methyl-2-oxaadamant-1-yl)amine hydrochloride
• 英文别名: 3-methyl-2-oxaadamantane-1-amine hydrochloride；3-Methyl-2-oxatricyclo[3.3.1.13,7]decan-1-amine;hydrochloride；3-methyl-2-oxatricyclo[3.3.1.13,7]decan-1-amine;hydrochloride
• CAS: 1160239-41-7
• 化学式: C₁₀H₁₇NO*ClH
• 分子量: 203.712
• InChiKey: VNOCQKRYVKVDCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.25
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3-methyl-2-oxaadamant-1-yl)amine hydrochloride 、 环己甲酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 以39%的产率得到N-(3-methyl-2-oxaadamant-1-yl)cyclohexanecarboxamide
  参考文献：
  名称：

  Novel 11β-HSD1 inhibitors: C-1 versus C-2 substitution and effect of the introduction of an oxygen atom in the adamantane scaffold

  摘要：

  The adamantane scaffold is found in several marketed drugs and in many investigational 11 beta-HSD1 inhibitors. Interestingly, all the clinically approved adamantane derivatives are C-1 substituted. We demonstrate that, in a series of paired adamantane isomers, substitution of the adamantane in C-2 is preferred over the substitution at C-1 and is necessary for potency at human 11 beta-HSD1. Furthermore, the introduction of an oxygen atom in the hydrocarbon scaffold of adamantane is deleterious to 11 beta-HSD1 inhibition. Molecular modeling studies provide a basis to rationalize these features. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.07.097
• 作为产物：
  描述：

  (1r,3s,5R,7S)-3-methyl-2-oxaadamantan-1-amine 在 盐酸 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 以3.60 g的产率得到(3-methyl-2-oxaadamant-1-yl)amine hydrochloride
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of (2-oxaadamant-1-yl)amines

  摘要：

  The synthesis of several (2-oxaadamant-1-yl) amines is reported. They were evaluated as NMDA receptor antagonists and several of them were more active than amantadine, but none was more potent than memantine. None of the tested compounds displayed antiviral activity. Two of the derivatives showed a significant level of trypanocidal activity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.007