2-methyl-2-(adamant-1-yl)aziridine | 888030-19-1

• 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: 2-methyl-2-(adamant-1-yl)aziridine
• 英文别名: 2-methyl-2-(adamantan-1-yl)aziridine；2-((3r,5r,7r)-adamantan-1-yl)-2-methylaziridine；2-(1-adamantyl)-2-methylaziridine
• CAS: 888030-19-1
• 化学式: C₁₃H₂₁N
• 分子量: 191.316
• InChiKey: XWAAISAHKXRPLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methyl-2-(adamant-1-yl)aziridine 在 (五甲基环戊二烯基)三氯化钛(IV) 、 C₃₀H₃₆CoF₆N₂O₂ 、 三乙胺 、 锌 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 N-(2-((3r,5r,7r)-adamantan-1-yl)allyl)benzamide
  参考文献：
  名称：

  用于 N-Bz 氮丙啶异构化为烯丙酰胺的钛钴双金属自由基氧化还原继电器

  摘要：

  本文采用双金属自由基氧化还原-中继策略，在钛(III)催化的温和条件下生成烷基自由基，并通过钴(II)催化的氢原子转移终止，以进行N -Bz氮丙啶到N -Bz的无碱异构化烯丙基酰胺。该反应提供了一种通过三步序列从烯烃合成烯丙基酰胺的替代策略，以完成正式的转位烯丙基胺化。

  DOI：

  10.1055/s-0037-1610779
• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 作用下， 生成 2-methyl-2-(adamant-1-yl)aziridine
  参考文献：
  名称：

  Heterocyclic rimantadine analogues with antiviral activity

  摘要：

  2-(1-Adamantyl)-2-methyl-pyrrolidines 3 and 4, 2-(1-adamatityl)-2-methyl-azetidines 5 and 6, and 2-(1-adamantyl)-2-methyl-aziridines 7 and 8 were synthesized and tested for their antiviral activity against influenza A. Parent molecules 3, 5, and 7 contain the alpha-methyl-1-adimantan-methanamine 2 pharmacophoric moiety (rimantadine). The ring size effect on anti-influenza A activity was investigated. Pyrrolidine 3 was the most potent anti-influenza virus A compound, 9-fold more potent than rimantadine 2, 27-fold more potent than amantadine 1, and 22-fold more potent than ribavirin. Azetidines 5 and 6 were both markedly active against influenza A H2N2 virus, 10- to 20-fold more potent than amantadine. Aziridine 7 was almost devoid of any activity against H2N2 virus but exhibited borderline activity against H3N2 influenza A strain. Thus, it appears that changing the five-, to four- to a three-membered ring results in a drop of activity against influenza A virus. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.12.056

文献信息

• Molecular design, synthesis and biological evaluation of cage compound-based inhibitors of hepatitis C virus p7 ion channels
  作者：Vadim A. Shiryaev、Eugene V. Radchenko、Vladimir A. Palyulin、Nikolay S. Zefirov、Nikolay I. Bormotov、Olga A. Serova、Larisa N. Shishkina、Marat R. Baimuratov、Kseniya M. Bormasheva、Yulia A. Gruzd、Elena A. Ivleva、Marina V. Leonova、Anton V. Lukashenko、Dmitry V. Osipov、Vitaliy A. Osyanin、Alexander N. Reznikov、Vera A. Shadrikova、Anastasia E. Sibiryakova、Ilya M. Tkachenko、Yuri N. Klimochkin

  DOI：10.1016/j.ejmech.2018.08.009

  日期：2018.10

  targets and having better pharmacological profile is highly desirable. The hepatitis C virus p7 viroporin is a relatively small hydrophobic oligomeric viral ion channel that plays a critical role during virus assembly and maturation, making it an attractive and validated target for the development of the cage compound-based inhibitors. Using the homology modeling, molecular dynamics, and molecular docking

  由丙型肝炎病毒（HCV）引起的丙型肝炎是一种急性和/或慢性肝病，其严重程度从轻度短暂疾病到严重的终生疾病，其影响全世界3％的人口，并给社会带来重大且不断增加的社会负担，经济和人文负担。在过去的十年中，通过针对非结构性病毒蛋白NS3 / 4A，NS5A和NS5B的直接作用抗病毒（DAA）药物的开发和临床实践，彻底改变了其治疗方法。然而，当前的治疗选择仍然具有重要的局限性，因此，迫切需要开发作用于不同病毒靶标并具有更好药理学特征的新型DAA。丙型肝炎病毒p7 viroporin是一个相对较小的疏水性寡聚病毒离子通道，在病毒组装和成熟过程中起着至关重要的作用，使其成为开发基于笼状化合物的抑制剂的有吸引力且经过验证的目标。使用同源性建模，分子动力学和分子对接技术，我们建立了具有代表性的丙型肝炎病毒p7离子通道模型（Gt1a，Gt1b，Gt1b_L20F，Gt2a和Gt2b），分析了抑制剂的结合位点
• Structural Transformations of 2-(Adamantan-1-Yl)Aziridines
  作者：Marina V. Leonova、Nadezhda V. Belaya、Marat R. Baimuratov、Victor B. Rybakov、Yuri N. Klimochkin

  DOI：10.1007/s10593-020-02696-3

  日期：2020.5

  of sterically hindered 2-(adamantan-1-yl)aziridine derivatives in the presence of trifluoroacetic anhydride are considered. In a reaction with trifluoroacetic anhydride, trans-2-(adamantan-1-yl)-3-methylaziridine forms the rearrangement product dihydro-1,3-oxazine condensed with homoadamantane, whereas 2-(adamantan-1-yl)aziridine forms a mixture of a derivative of oxazine and N-[1-(adamantan-1-yl)-2-hydroxyethyl]-2

  考虑了在三氟乙酸酐存在下空间受阻的2-（金刚烷-1-基）氮丙啶衍生物的转化的细节。在与三氟乙酸酐的反应中，反式-2-（金刚烷-1-基）-3-甲基氮丙啶形成与高金刚烷缩合的重排产物二氢-1,3-恶嗪，而2-（金刚烷-1-基）氮丙啶形成恶嗪衍生物与N- [1-（金刚烷-1-基）-2-羟乙基] -2,2,2-三氟乙酰胺的混合物的比例相等。
• Synthesis and Transformations of 2-(Adamantan-1-yl)aziridine
  作者：M. V. Leonova、N. V. Belaya、M. R. Baimuratov、Yu. N. Klimochkin

  DOI：10.1134/s1070428018110040

  日期：2018.11

  Mono- and disubstituted aziridines derived from sterically hindered olefins of the adamantane series are synthesized. The opening of the aziridine ring under the action of acids is quite a regio- and stereoselective process. Depending on the nature of the nucleophilic agent, the opening of the 2,2-disubstituted aziridine ring can occur by the S(N)1 or S(N)2 mechanism.