2-甲基-1-(2-丙炔-1-基)-1H-咪唑 | 82418-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-甲基-1-(2-丙炔-1-基)-1H-咪唑
• 英文名称: 2-methyl-1-(prop-2-yn-1-yl)-1H-imidazole
• 英文别名: 2-Methyl-1-prop-2-ynylimidazole
• CAS: 82418-40-4
• 化学式: C₇H₈N₂
• 分子量: 120.154
• InChiKey: NBDYHRSJLDRXNG-UHFFFAOYSA-N

物化性质

• 沸点：
  235.4±23.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-甲基-1-(2-丙炔-1-基)-1H-咪唑 在 bis-triphenylphosphine-palladium(II) chloride 、 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 铜 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (±)-4-(3-(2-((2R)-2-hydroxy-7-azabicyclo[2.2.1]heptan-7-yl)acetyl)-2-methyl-5-((E)-3-(2-methyl-1H-imidazol-1-yl)prop-1-en-1-yl)-1H-pyrrol-1-yl)benzonitrile
  参考文献：
  名称：

  WO2020006296A5

  摘要：

  公开号：

  WO2020006296A5
• 作为产物：
  描述：

  2-甲基咪唑 、 3-氯丙炔 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-甲基-1-(2-丙炔-1-基)-1H-咪唑
  参考文献：
  名称：

  Ehrhardt, Heinz; Mildenberger, Hilmar, Liebigs Annalen der Chemie, 1982, # 5, p. 989 - 993

  摘要：

  DOI：

文献信息

• Copper-Catalyzed Hydroamination of <i>N</i> -Allenylazoles: Access to Amino-Substituted <i>N</i> -Vinylazoles
  作者：Luca Alessandro Perego、Rémi Blieck、Julie Michel、Ilaria Ciofini、Laurence Grimaud、Marc Taillefer、Florian Monnier

  DOI：10.1002/adsc.201700965

  日期：2017.12.19

  and simple procedure for the hydroamination of N‐allenylazoles with secondary amines. The reaction proceeds under mild conditions by copper(I) catalysis yielding the corresponding original linear E allylic amines with total regio‐ and stereoselectivity. Density Functional Theory (DFT) calculations offer a mechanistic explanation of the significantly higher reactivity of N‐allenyl‐(1,2)‐azoles compared

  在机理研究的基础上，已利用吡咯类化合物作为引导基团的先天能力来设计一种有效而简单的程序，用于将N-烯丙基唑类化合物与仲胺进行加氢胺化。在铜（I）催化下，反应在温和条件下进行，得到相应的原始线性E烯丙基胺，具有总的区域和立体选择性。密度泛函理论（DFT）计算提供了一种机械解释，表明N-烯丙基-（1,2）-吡咯的反应活性明显高于其1,3-类似物，这是由于类似吡啶的反应增强了配位作用氮到达铜中心。
• Design and synthesis of N-substituted-2-hydroxyiminoacetamides and interactions with cholinesterases
  作者：Nikola Maraković、Anamarija Knežević、Vladimir Vinković、Zrinka Kovarik、Goran Šinko

  DOI：10.1016/j.cbi.2016.05.035

  日期：2016.11

  Within this study, we designed and synthesized four new oxime compounds of the N-substituted 2-hydroxyiminoacetamide structure and evaluated their interactions with acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Our aim was to explore the possibility of extending the dual-binding mode of interaction between the enzyme and the inhibitor to a so-called triple-binding mode of interaction through the introduction of an additional binding moiety. N-substituted 2-hydroxyiminoacetamide 1 was prepared via BOP catalyzed amidation of hydroxyiminoacetic acid with 3-azido-1-phenylpropylamine. An azide group enabled us to prepare more elaborate structures 2-4 by the copper-catalyzed azide-alkyne cycloaddition. The new compounds 1-4 differed in their presumed AChE peripheral site binding moiety, which ranged from an azide group to functionalized heterocycles. Molecular docking studies revealed that all three binding moieties are involved in the non-covalent interactions with ChEs for all of the four compounds, albeit not always in the complete accordance with the proposed hypothesis. All of the four compounds reversibly inhibited the ChEs with their inhibition potency increasing in the same order for both enzymes (1 < 2 < 4 < 3). A higher preference for binding to BChE (K-I from 0.30 mu mol/L to 130 mu mol/L) over AChE (K-I from 50 mmol/L to 1200 mmol/L) was observed for all of the compounds. Compounds were screened for reactivation of cyclosarin-, sarin-and VX-inhibited AChE and BChE. (C) 2016 Elsevier Ireland Ltd. All rights reserved.
• EHRHARDT, H.;MILDENBERGER, H., LIEBIGS ANN. CHEM., 1982, N 5, 989-993
  作者：EHRHARDT, H.、MILDENBERGER, H.

  DOI：——

  日期：——
• QINOLINE DERIVATIVES INHIBITING THE EFFECT OF GROWTH FACTORS SUCH AS VEGF
  申请人：AstraZeneca AB

  公开号：EP0929526B1

  公开（公告）日：2005-07-27
• OXINDOLYLQUINAZOLINE DERIVATIVES AS ANGIOGENESIS INHIBITORS
  申请人：AstraZeneca AB

  公开号：EP1005470B1

  公开（公告）日：2007-08-01