2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl acrylate | 206362-27-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl acrylate
• 英文别名: acrylic acid 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl ester；2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl 2-propenoate；2-(2-methyl-5-nitroimidazol-1-yl)ethyl prop-2-enoate
• CAS: 206362-27-8
• 化学式: C₉H₁₁N₃O₄
• 分子量: 225.204
• InChiKey: MAWGIUDKGUTHLG-UHFFFAOYSA-N

物化性质

• 熔点：
  42-43 °C
• 沸点：
  419.4±25.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl acrylate 、 2-甲基-4-硝基咪唑 在 三乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 以81%的产率得到3-(2-methyl-5-nitro-1H-imidazol-1-yl)-propionic acid 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl ester
  参考文献：
  名称：

  Imidazole derivatives as possible microbicides with dual protection

  摘要：

  Twenty seven derivatives (2-28) of 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol were synthesized and evaluated for anti-trichomonas, spermicidal and antifungal activities. Twenty six compounds were active against Trichomonas vaginalis at MIC ranging from 1-42 mu M and seven compounds (9,18,19,22,24,26,28) immobilized 100% human spermatozoa at 1% concentration (w/v). Twenty three compounds (2,3,5,8-26,28) exhibited antifungal activity at 25-50 mu g/mL concentration. Seven compounds (9,18,19,22,24,26,28) showed significant anti-trichomonas and spermicidal activities and also exhibited mild antifungal activity. All the compounds were highly safe towards human cervical cell line (HeLa) as shown by the cell-viability assay of HeLa cells at 200 mu g/mL concentration, whereas nonoxynol-9 (N-9, the marketed spermicidal microbicide) was highly cytotoxic. Therefore, it may be concluded that introduction of the pharmacophore responsible for spermicidal activity into a proven anti-trichomonas structure may lead to a potent dual function microbicide better and safer than N-9. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.021
• 作为产物：
  描述：

  甲硝唑 、 丙烯酰氯 在 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 24.0h， 生成 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl acrylate
  参考文献：
  名称：

  一种含甲硝唑的药物单体及其制备方法

  摘要：

  本发明公开了一种含甲硝唑的药物单体及其制备方法。具体地说，是以甲硝唑和丙烯酰胺为原料，在一定的条件下反应生成2‑(2‑甲基‑5‑硝基‑1H‑咪唑‑1‑基)乙基丙烯酸酯，并对产物进行核磁表征。2‑(2‑甲基‑5‑硝基‑1H‑咪唑‑1‑基)乙基丙烯酸酯同时具有硝基咪唑基团和丙烯酸酯基团。硝基咪唑基团具有低氧响应性，丙烯酸酯基团可以进行自由基聚合或者与巯基、氨基等进行迈克尔加成反应，因此该单体可对聚合物进行修饰，使其带有硝基咪唑基团，从而获得具有低氧响应性的聚合物，在生物工程领域有着潜在的应用价值。

  公开号：

  CN112552240A

文献信息

• Palladium‐Catalyzed Enantioselective C−H Olefination to Access Planar‐Chiral Cyclophanes by Dynamic Kinetic Resolution
  作者：Ziyang Dong、Jia Li、Ting Yao、Changgui Zhao

  DOI：10.1002/anie.202315603

  日期：2023.12.18

  enantioselective C−H olefination of prochiral cyclophanes has been disclosed. The low rotational barrier of less hindered benzene ring in the substrates allows the reaction to proceed through a dynamic kinetic resolution. The chirality of the resulted cyclophanes arises from the bond rotation constraint of the benzene ring around the macrocycle plane, rather than the C−N axis.

  首次公开了 Pd(II) 催化的前手性环烷的对映选择性 CH 烯化反应。底物中受阻较少的苯环的低旋转势垒允许反应通过动态动力学拆分进行。所得环烷的手性来自苯环围绕大环平面的键旋转约束，而不是 C−N 轴。
• Imidazole derivatives as possible microbicides with dual protection
  作者：Lalit Kumar、Amit Sarswat、Nand Lal、Vishnu L. Sharma、Ashish Jain、Rajeev Kumar、Vikas Verma、Jagdamba P. Maikhuri、Awanit Kumar、Praveen K. Shukla、Gopal Gupta

  DOI：10.1016/j.ejmech.2009.10.021

  日期：2010.2

  Twenty seven derivatives (2-28) of 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol were synthesized and evaluated for anti-trichomonas, spermicidal and antifungal activities. Twenty six compounds were active against Trichomonas vaginalis at MIC ranging from 1-42 mu M and seven compounds (9,18,19,22,24,26,28) immobilized 100% human spermatozoa at 1% concentration (w/v). Twenty three compounds (2,3,5,8-26,28) exhibited antifungal activity at 25-50 mu g/mL concentration. Seven compounds (9,18,19,22,24,26,28) showed significant anti-trichomonas and spermicidal activities and also exhibited mild antifungal activity. All the compounds were highly safe towards human cervical cell line (HeLa) as shown by the cell-viability assay of HeLa cells at 200 mu g/mL concentration, whereas nonoxynol-9 (N-9, the marketed spermicidal microbicide) was highly cytotoxic. Therefore, it may be concluded that introduction of the pharmacophore responsible for spermicidal activity into a proven anti-trichomonas structure may lead to a potent dual function microbicide better and safer than N-9. (C) 2009 Elsevier Masson SAS. All rights reserved.
• 一种含甲硝唑的药物单体及其制备方法
  申请人：天津大学

  公开号：CN112552240A

  公开（公告）日：2021-03-26

  本发明公开了一种含甲硝唑的药物单体及其制备方法。具体地说，是以甲硝唑和丙烯酰胺为原料，在一定的条件下反应生成2‑(2‑甲基‑5‑硝基‑1H‑咪唑‑1‑基)乙基丙烯酸酯，并对产物进行核磁表征。2‑(2‑甲基‑5‑硝基‑1H‑咪唑‑1‑基)乙基丙烯酸酯同时具有硝基咪唑基团和丙烯酸酯基团。硝基咪唑基团具有低氧响应性，丙烯酸酯基团可以进行自由基聚合或者与巯基、氨基等进行迈克尔加成反应，因此该单体可对聚合物进行修饰，使其带有硝基咪唑基团，从而获得具有低氧响应性的聚合物，在生物工程领域有着潜在的应用价值。