2-bromo-N,N-dimethyl-2-nitroethenamine | 26507-23-3

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-bromo-N,N-dimethyl-2-nitroethenamine
• 英文别名: 1-Nitro-1-brom-2-dimethylamino-aethylen
• CAS: 26507-23-3
• 化学式: C₄H₇BrN₂O₂
• 分子量: 195.016
• InChiKey: LYKZYHPHABGFPO-UHFFFAOYSA-N

物化性质

• 沸点：
  181.1±35.0 °C(Predicted)
• 密度：
  1.609±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.02
• 重原子数：
  9.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.38
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-bromo-N,N-dimethyl-2-nitroethenamine 、 硫脲 在 盐酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以75 %的产率得到2-氨基-5-硝基噻唑
  参考文献：
  名称：

  [EN] AN IMPROVED PROCESS FOR THE PREPARATION OF NITAZOXANIDE AND INTERMEDIATES THEREOF
  [FR] PROCÉDÉ AMÉLIORÉ POUR PRÉPARER DU NITAZOXANIDE ET DE SES INTERMÉDIAIRES

  摘要：

  The present invention relates to the process for the preparation of Nitazoxanide and intermediates thereof. The invention explores readily available starting materials with reaction conditions that are suitable for industrial scale applications. The present invention discloses, a single vessel process to prepare 5-nitrothiazol-2-amine starting from a very basic starting material 1,1-dimethoxy-N, N-dimethylmethanamine. Overall intermediates throughout the process is free from column chromatography and the final product Nitazoxanide is purified by precipitation. All the synthesized compounds were confirmed by various spectroscopic techniques such as Fourier transform infrared spectroscopy,1H NMR,13C NMR, HRMS and elemental analysis.

  公开号：

  WO2023058046A1
• 作为产物：
  描述：

  1-(二甲氨基)-2-硝基乙烯 生成 2-bromo-N,N-dimethyl-2-nitroethenamine
  参考文献：
  名称：

  乙炔，电子负离子和电子负离子† ‡

  摘要：

  可以通过溴化和消除HBr，从相应取代的烯烃以高收率获得同时具有给电子基团和电子接受基团（1）的乙炔。乙炔醛1a与质子酸的反应在伯加合物重排后产生β-取代的丙烯酰胺。亲核试剂的加入导致β-二取代的α.β-不饱和羰基化合物。用肼得到吡唑和吡唑啉酮。乙炔1经历[2 + 2]-，[2 + 3]-和[2 + 4]-环加成反应。

  DOI：

  10.1002/hlca.19690520845

文献信息

• Development of 5-nitrothiazole derivatives: Identification of leads against both replicative and latent Mycobacterium tuberculosis
  作者：Variam Ullas Jeankumar、Manoj Chandran、Ganesh Samala、Mallika Alvala、Pulla Venkat Koushik、Perumal Yogeeswari、Elena G. Salina、Dharmarajan Sriram

  DOI：10.1016/j.bmcl.2012.10.060

  日期：2012.12

  Twenty eight 5-nitrothiazole derivatives were synthesized and evaluated for in vitro activities against Mycobacterium tuberculosis (MTB), cytotoxicity against HEK 293T. Among the compounds, 5-nitro-N-(5-nitrothiazol-2-yl)furan-2-carboxamide (20) was found to be the most active compound in vitro with MICs of 5.48 mu M against log-phase culture of MTB and also non-toxic up to 100 mu M. (C) 2012 Elsevier Ltd. All rights reserved.