N-(1-adamantyl)-α-iodoacetamide | 136860-55-4

• 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-(1-adamantyl)-α-iodoacetamide
• 英文别名: N-iodoacetyl-1-aminoadamantane；N-(iodoacetyl)adamantan-1-amine；N-(adamantan-1-yl)-2-iodoacetamide；N-(1-adamantyl)-2-iodoacetamide
• CAS: 136860-55-4
• 化学式: C₁₂H₁₈INO
• 分子量: 319.186
• InChiKey: ZJLGCWVWKXPRDX-UHFFFAOYSA-N

物化性质

• 沸点：
  417.1±24.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(1-adamantyl)-α-iodoacetamide 、 二乙醇胺 在 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 N-Adamantan-1-yl-2-[bis-(2-hydroxy-ethyl)-amino]-acetamide
  参考文献：
  名称：

  Synthesis and investigation of viral-inhibitory activity of nitrogen-containing derivatives of adamantane

  摘要：

  DOI：

  10.1007/bf00772005
• 作为产物：
  描述：

  2-碘乙酰胺 、 1-金刚烷醇 在 硫酸 作用下， 反应 2.0h， 以71%的产率得到N-(1-adamantyl)-α-iodoacetamide
  参考文献：
  名称：

  Synthesis and investigation of viral-inhibitory activity of nitrogen-containing derivatives of adamantane

  摘要：

  DOI：

  10.1007/bf00772005

文献信息

• Addition of lithium carbenoids to isocyanates: a direct access to synthetically useful N-substituted 2-haloacetamides
  作者：Vittorio Pace、Laura Castoldi、Wolfgang Holzer

  DOI：10.1039/c3cc44255a

  日期：——

  presence of variously functionalized substituents on the nitrogen atom, including sterically demanding ones and reactive halogens. No erosion of the enantiopurity was observed in the case of optically active isocyanates. One of the substrates prepared has been employed in Charette's type chemoselective addition of a Grignard reagent to access an alpha-chloroketone.

  向异氰酸酯中添加类胡萝卜酸锂可提供N-取代的2-卤代乙酰胺的通用途径：该反应可耐受氮原子上存在各种官能化的取代基，包括空间上需要的取代基和反应性卤素。在光学活性异氰酸酯的情况下，未观察到对映体纯度的侵蚀。所制备的底物之一已用于格氏试剂的Charette型化学选择性添加中，从而获得α-氯酮。
• Synthesis and Chemical Transformations of N-Adamantylated Amides
  作者：Yu. N. Klimochkin、E. A. Ivleva

  DOI：10.1134/s1070428022050050

  日期：2022.5

  Abstract N-Adamantylated amides have been synthesized from 1-adamantyl nitrate. The reactions were carried out in the sulfuric acid media. The proposed method is usefulness for the preparation of antiviral drug tromantadine. A number of new cage aminoamides have been synthesized by reactions of N-(1-adamantyl)-2-chloroacetamide with nitrogen-containing nucleophiles. with potential biological activity

  摘要 N-金刚烷基化的酰胺是由 1-金刚烷基硝酸盐合成的。反应在硫酸介质中进行。所提出的方法可用于制备抗病毒药物曲金刚乙胺。N -(1-金刚烷基)-2-氯乙酰胺与含氮亲核试剂反应合成了许多新的笼形氨基酰胺。具有潜在的生物活性。
• Homologation of Isocyanates with Lithium Carbenoids: A Straightforward Access to α-Halomethyl- and α,α-Dihalomethylamides
  作者：Vittorio Pace、Laura Castoldi、Ashenafi Mamuye、Wolfgang Holzer

  DOI：10.1055/s-0034-1379209

  日期：——

  Treatment of widely available isocyanates with monohalolithium and dihalolithium carbenoids provides a valuable protocol for the one-pot preparation of -halo- and ,-dihaloacetamide derivatives. While monohalolithium carbenoids can be prepared by a smooth lithium-halogen exchange, the preparation of the corresponding dihalo compounds proved to be highly dependent on the base used to realize the deprotonation, with lithium 2,2,6,6-tetramethylpiperidine emerging as optimal. The clear advantages of the procedure are: (a) broad scope of isocyanates that can be employed; (b) preservation of the optical purity when chiral materials are used; (c) divergent access to different haloamides by simply selecting the homologating agents. We also report an application of Charette's imidoyl triflate activation of a secondary amide to the synthesis of an -chloro ketone and N-15 NMR data for selected compounds.