4-(4-(chloromethyl)phenyl)-1,2-dimethyl-5-nitro-1H-imidazole | 1332315-16-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-(chloromethyl)phenyl)-1,2-dimethyl-5-nitro-1H-imidazole
• 英文别名: 4-[4-(chloromethyl)phenyl]-1,2-dimethyl-5-nitro-1H-imidazole；4-[4-(Chloromethyl)phenyl]-1,2-dimethyl-5-nitroimidazole；4-[4-(chloromethyl)phenyl]-1,2-dimethyl-5-nitroimidazole
• CAS: 1332315-16-8
• 化学式: C₁₂H₁₂ClN₃O₂
• 分子量: 265.699
• InChiKey: WHAXTXLURFAFPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-(chloromethyl)phenyl)-1,2-dimethyl-5-nitro-1H-imidazole 在 2-硝基丙烷钠盐 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 72.0h， 生成 4-(1,2-dimethyl-5-nitro-1H-imidazol-4-yl)benzaldehyde
  参考文献：
  名称：

  Long distance-SRN1 in nitroimidazole series favored by temperature

  摘要：

  New reductive alkylating agents in 4- and 5-nitroimidazole series produce exclusively O-alkylation with nitronate anions under classical S(RN)1 conditions at room temperature. Electron-transfer C-alkylation is observed under microwave irradiation or under conventional heating. Furthermore, X-ray spectroscopy shows that the dihedral angles between the phenyl and imidazole rings for the two series are different, which could greatly influence reactivity in 4- and 5-nitroimidazole series. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.096
• 作为产物：
  描述：

  4-羟甲基苯硼酸 在 四(三苯基膦)钯 、 氯化亚砜 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 17.0h， 生成 4-(4-(chloromethyl)phenyl)-1,2-dimethyl-5-nitro-1H-imidazole
  参考文献：
  名称：

  5-硝基-1H-咪唑衍生物的高度官能化：TDAE 方法

  摘要：

  我们在此报告了取代的 2--[4-(1,2-二甲基-5-硝基-1H-咪唑-4-基)苯基]-1-芳基乙醇、乙基 3-[4-(1,2-二甲基-5-硝基-1H-咪唑-4-基)-苯基]-2-羟基丙酸酯和2-[4-(1,2-二甲基-5-硝基-1H-咪唑-4-基)苄基]-2 -羟基-苊-1(2H)-来自 4-[4-(氯甲基)苯基]-1,2-二甲基-5-硝基-1H-咪唑与各种芳香羰基和α-羰基酯衍生物的反应，使用四（二甲氨基）乙烯（TDAE）方法。

  DOI：

  10.3390/molecules16086883

文献信息

• Mild and Metal-Free Diastereoselective Synthesis of N-tert-Butanesulfinylamines by Using Tetrakis(dimethylamino)ethylene
  作者：Patrice Vanelle、Cédric Spitz、Anna Lin、Thierry Terme

  DOI：10.1055/s-0034-1378636

  日期：——

  on tetrakis(dimethylamino)ethylene. Good yields and diastereo­selectivities were achieved by addition of o-nitrobenzyl chloride or 4-[4-(chloromethyl)phenyl]-1,2-dimethyl-5-nitro-1H-imidazole to readily available N-tert-butanesulfinimines. A mild and metal-free diastereoselective synthesis of N-tert-butanesulfinylamines was developed by using a strategy based on tetrakis(dimethylamino)ethylene. Good

  摘要 的温和和无金属非对映选择性合成ñ -叔-butanesulfinylamines通过使用基于四（二甲基氨基）乙烯的策略开发的。良好的产率和非对映选择性通过加入实现ö硝基苄酰氯或4- [4-（氯甲基）苯基] -1,2-二甲基-5-硝基-1- ħ咪唑到容易获得ñ -叔-butanesulfinimines。 的温和和无金属非对映选择性合成ñ -叔-butanesulfinylamines通过使用基于四（二甲基氨基）乙烯的策略开发的。良好的产率和非对映选择性通过加入实现ö硝基苄酰氯或4- [4-（氯甲基）苯基] -1,2-二甲基-5-硝基-1- ħ咪唑到容易获得ñ -叔-butanesulfinimines。
• Practical and Metal-Free Synthesis of Novel Enantiopure Amides Containing the Potentially Bioactive 5-Nitroimidazole Moiety
  作者：Cédric Spitz、Fanny Mathias、Alain Giuglio-Tonolo、Thierry Terme、Patrice Vanelle

  DOI：10.3390/molecules21111472

  日期：——

  practical and metal-free synthesis of novel enantiopure amides containing the drug-like 5-nitroimidazole scaffold. The first step was a metal-free diastereoselective addition of 4-(4-(chloromethyl)phenyl)-1,2-dimethyl-5-nitro-1H-imidazole to enantiomerically pure N-tert-butanesulfinimine. Then, the N-tert-butanesulfinyl-protected amine was easily deprotected under acidic conditions. Finally, the primary

  我们在这里报告了实用和无金属合成的新型对映纯酰胺类药物的5-硝基咪唑支架。第一步是将4-（4-（氯甲基）苯基）-1,2-二甲基-5-硝基-1H-咪唑进行无金属非对映选择性加成对映体纯的N-叔丁烷亚磺酰亚胺。然后，在酸性条件下，容易将N-叔丁烷亚磺酰基保护的胺脱保护。最后，将伯胺与不同的酰氯或酸偶合，得到相应的酰胺。温和的反应条件和对各种取代基的高耐受性使该方法对于构建具有药理意义的5-硝基咪唑具有吸引力。
• Long distance-SRN1 in nitroimidazole series favored by temperature
  作者：Laura Zink、Maxime D. Crozet、Thierry Terme、Patrice Vanelle

  DOI：10.1016/j.tetlet.2011.10.096

  日期：2011.12

  New reductive alkylating agents in 4- and 5-nitroimidazole series produce exclusively O-alkylation with nitronate anions under classical S(RN)1 conditions at room temperature. Electron-transfer C-alkylation is observed under microwave irradiation or under conventional heating. Furthermore, X-ray spectroscopy shows that the dihedral angles between the phenyl and imidazole rings for the two series are different, which could greatly influence reactivity in 4- and 5-nitroimidazole series. (C) 2011 Elsevier Ltd. All rights reserved.
• High Functionalization of 5-Nitro-1H-imidazole Derivatives: The TDAE Approach
  作者：Thierry Juspin、Laura Zink、Maxime D. Crozet、Thierry Terme、Patrice Vanelle

  DOI：10.3390/molecules16086883

  日期：——

  We report herein the synthesis of substituted 2--[4-(1,2-dimethyl-5-nitro-1H-imidazol-4-yl)phenyl]-1-arylethanols, ethyl 3-[4-(1,2-dimethyl-5-nitro-1H-imidazol-4-yl)-phenyl]-2-hydroxypropanoate and 2-[4-(1,2-dimethyl-5-nitro-1H-imidazol-4-yl)benzyl]-2-hydroxy-acenaphthylen-1(2H)-one from the reactions of 4-[4-(chloromethyl)phenyl]-1,2-dimethyl-5-nitro-1H-imidazole with various aromatic carbonyl and

  我们在此报告了取代的 2--[4-(1,2-二甲基-5-硝基-1H-咪唑-4-基)苯基]-1-芳基乙醇、乙基 3-[4-(1,2-二甲基-5-硝基-1H-咪唑-4-基)-苯基]-2-羟基丙酸酯和2-[4-(1,2-二甲基-5-硝基-1H-咪唑-4-基)苄基]-2 -羟基-苊-1(2H)-来自 4-[4-(氯甲基)苯基]-1,2-二甲基-5-硝基-1H-咪唑与各种芳香羰基和α-羰基酯衍生物的反应，使用四（二甲氨基）乙烯（TDAE）方法。