N-(adamantan-2-yl)cyclohexanecarboxamide | 325820-49-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(adamantan-2-yl)cyclohexanecarboxamide
• 英文别名: N-(2-adamantyl)cyclohexanecarboxamide
• CAS: 325820-49-3
• 化学式: C₁₇H₂₇NO
• 分子量: 261.407
• InChiKey: PHXXNOOSGAGIII-UHFFFAOYSA-N

物化性质

• 沸点：
  442.2±12.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)
• 溶解度：
  1.6 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-金刚烷胺盐酸盐 、 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71%的产率得到N-(adamantan-2-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

文献信息

• Photoinduced, Copper-Catalyzed Alkylation of Amides with Unactivated Secondary Alkyl Halides at Room Temperature
  作者：Hien-Quang Do、Shoshana Bachman、Alex C. Bissember、Jonas C. Peters、Gregory C. Fu

  DOI：10.1021/ja4126609

  日期：2014.2.5

  The development of a mild and general method for the alkylation of amides with relatively unreactive alkyl halides (i.e., poor substrates for SN2 reactions) is an ongoing challenge in organic synthesis. We describe herein a versatile transition-metal-catalyzed approach: in particular, a photoinduced, copper-catalyzed monoalkylation of primary amides. A broad array of alkyl and aryl amides (as well as

  开发一种温和而通用的方法，用相对不活泼的卤代烷（即 SN2 反应的不良底物）对酰胺进行烷基化是有机合成中的一个持续挑战。我们在此描述了一种通用的过渡金属催化方法：特别是光诱导、铜催化的伯酰胺单烷基化。一系列广泛的烷基和芳基酰胺（以及内酰胺和 2-恶唑烷酮）与未活化的仲（和受阻伯）烷基溴和碘结合使用一组相对简单和温和的条件：廉价的 CuI 作为催化剂，无需单独添加配体，并在室温下形成 CN 键。该方法与多种官能团兼容，例如烯烃、氨基甲酸酯、噻吩和吡啶，并已应用于阿片受体拮抗剂的合成。一系列机械观察，包括反应性和立体化学研究，与耦合途径一致，包括铜-酰胺络合物的光激发，然后是电子转移以形成烷基。
• Novel 11β-HSD1 inhibitors: C-1 versus C-2 substitution and effect of the introduction of an oxygen atom in the adamantane scaffold
  作者：Rosana Leiva、Constantí Seira、Andrew McBride、Margaret Binnie、F. Javier Luque、Axel Bidon-Chanal、Scott P. Webster、Santiago Vázquez

  DOI：10.1016/j.bmcl.2015.07.097

  日期：2015.10

  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.