N-[1-(adamantan-1-yl)ethyl]acetamide | 127619-43-6

• 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-(adamantan-1-yl)ethyl]acetamide
• 英文别名: N-(1-adamantylethyl)acetamide；N-[1-(1-adamantyl)ethyl]acetamide
• CAS: 127619-43-6
• 化学式: C₁₄H₂₃NO
• mdl: MFCD00181719
• 分子量: 221.343
• InChiKey: HDEIBESKFFIEPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.928
• 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-(adamantan-1-yl)ethyl]acetamide 在 硫酸 、 硝酸 、 水 、 sodium hydroxide 作用下， 反应 3.0h， 以51%的产率得到N-[1-(3-hydroxyadamantan-1-yl)ethyl]acetamide
  参考文献：
  名称：

  基于N-[（金刚烷-1-基）烷基]乙酰胺的金刚烷官能衍生物的合成

  摘要：

  以N -[（金刚烷-1-基）烷基]-乙酰胺为原料合成了一系列新的多官能衍生物。反应在酸性介质中进行。所获得的化合物可以被认为是构象受限的拟肽合成的基础。

  DOI：

  10.1134/s1070428016110026
• 作为产物：
  描述：

  盐酸金刚乙胺 、 乙酰氯 在 氢氧化钾 作用下， 以 乙醚 、 水 为溶剂， 反应 0.25h， 以95%的产率得到N-[1-(adamantan-1-yl)ethyl]acetamide
  参考文献：
  名称：

  Synthesis and antiviral activity of metabolites of rimantadine

  摘要：

  The hydroxy metabolites of rimantadine (3-5) were synthesized and compared to amantadine (1) and rimantadine (2) for their ability to inhibit the replication of influenza viruses in vitro. All three metabolites were inhibitory to wild-type influenza A viruses (H3N2 and H1N1). In particular, 2-hydroxyrimantadine (3) showed similar activity to amantadine, but the 3- and 4-hydroxy metabolites (4 and 5, respectively), both of which are found in rimantadine-treated patients, showed only modest inhibitory activity. A rimantadine-resistant isolate of influenza A virus exhibited cross-resistance to amantadine and to each of the metabolites 3-5. None of the compounds were effective against influenza B virus.

  DOI：

  10.1021/jm00169a029

文献信息

• Selcetive biohydroxylation of 1-substituted adamantanes using Absidia cylindrospora(I.M.I. 342950)
  作者：Patrick D. Bailey、Stanley D. Higgins、Colin H. Ridyard、Stanley M. Roberts、Georgina M. Rosair、Roger A. Whittaker、Andrew J. Willetts

  DOI：10.1039/cc9960001833

  日期：——

  The biohydroxylation of 1-substituted adamantanes using Absidia cylindrospora in a whole-cell oxidation system exclusively generated 3-hydroxy and 4ax-hydroxy derivatives; the assignments were confirmed by three X-ray crystal structure determinations.

  利用Absidia cylindrospora的全细胞氧化系统对1-取代金刚烷的生物羟基化反应中，仅生成3-羟基和4轴向-羟基衍生物；这些产物通过三个X射线晶体结构测定得到了确认。
• MANCHAND, PERCY S.;CERRUTI, RICHARD L.;MARTIN, JOSEPH A.;HILL, CHRISTOPHE+, J. MED. CHEM., 33,(1990) N, C. 1992-1995
  作者：MANCHAND, PERCY S.、CERRUTI, RICHARD L.、MARTIN, JOSEPH A.、HILL, CHRISTOPHE+

  DOI：——

  日期：——
• The unusual reaction of 2-isocyanatophenyl acetate with amines and water
  作者：Boris P. Gladkikh、Vladimir S. D'yachenko、Vladimir V. Burmistrov、Gennady M. Butov、Ivan A. Novakov

  DOI：10.1016/j.mencom.2022.09.039

  日期：2022.9
• Synthesis of adamantane functional derivatives basing on N-[(adamantan-1-yl)alkyl]acetamides
  作者：E. A. Ivleva、I. M. Tkachenko、Yu. N. Klimochkin

  DOI：10.1134/s1070428016110026

  日期：2016.11

  A series of new polyfunctional derivatives was synthesized with use of N-[(adamantan-1-yl)alkyl]-acetamides as a starting material. The reactions were carried out in acid media. The obtained compounds could be considered as a building blocks for the synthesis of conformationally restricted peptidomimetics.

  以N -[（金刚烷-1-基）烷基]-乙酰胺为原料合成了一系列新的多官能衍生物。反应在酸性介质中进行。所获得的化合物可以被认为是构象受限的拟肽合成的基础。
• Synthesis and antiviral activity of metabolites of rimantadine
  作者：Percy S. Manchand、Richard L. Cerruti、Joseph A. Martin、Christopher H. Hill、John H. Merrett、Elizabeth Keech、Robert B. Belshe、Edward V. Connell、Iain S. Sim

  DOI：10.1021/jm00169a029

  日期：1990.7

  The hydroxy metabolites of rimantadine (3-5) were synthesized and compared to amantadine (1) and rimantadine (2) for their ability to inhibit the replication of influenza viruses in vitro. All three metabolites were inhibitory to wild-type influenza A viruses (H3N2 and H1N1). In particular, 2-hydroxyrimantadine (3) showed similar activity to amantadine, but the 3- and 4-hydroxy metabolites (4 and 5, respectively), both of which are found in rimantadine-treated patients, showed only modest inhibitory activity. A rimantadine-resistant isolate of influenza A virus exhibited cross-resistance to amantadine and to each of the metabolites 3-5. None of the compounds were effective against influenza B virus.