N,N-dimethyl-4'-nitrophenylethynesulfonamide | 110417-51-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N-dimethyl-4'-nitrophenylethynesulfonamide
• 英文别名: (4-Nitro-phenyl)-ethynesulfonic acid dimethylamide；N,N-dimethyl-2-(4-nitrophenyl)ethynesulfonamide
• CAS: 110417-51-1
• 化学式: C₁₀H₁₀N₂O₄S
• 分子量: 254.266
• InChiKey: DIOIDWKAWJJOHA-UHFFFAOYSA-N

物化性质

• 熔点：
  154 °C (decomp)
• 沸点：
  405.4±47.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-N-dimethyl-2-oxo-2-(4'-nitrophenyl)ethanesulfonamide 在 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到N,N-dimethyl-4'-nitrophenylethynesulfonamide
  参考文献：
  名称：

  取代乙炔磺酰胺的简单通用合成

  摘要：

  通过两步操作制备了各种取代的2-芳基乙炔磺酰胺：1.通过适当的甲磺酰胺碳负离子与取代的苯甲酸酯反应制备2-氧代-2-芳基乙磺酰胺，2.通过2-脱水生成的酮氯-N-甲基吡啶碘化物/ NEt 3。

  DOI：

  10.1016/s0040-4039(00)97493-8

文献信息

• Synthesis and Reactivity of α-Diazo-β-keto Sulfonamides
  作者：Stuart G. Collins、Anita R. Maguire、Evan R. Judge、Keith O’Shaughnessy、Simon E. Lawrence

  DOI：10.1055/a-2348-5631

  日期：2024.12

  Copper-mediated reactions of α-diazo-β-keto sulfonamides led to a range of products, including alkynesulfonamides, enamines, and α-halosulfonamides, with no evidence for intramolecular C–H insertion in any of the reactions, in contrast to the reactivity of the comparable α-diazo-β-oxo sulfones. Use of copper(II) triflate (5 mol%) led to the isolation of a series of alkynesulfonamides (up to 12% yield)

  α-重氮-β-酮磺酰胺的铜介导反应产生了一系列产物，包括炔磺酰胺、烯胺和 α-卤代磺酰胺，与反应性相反，没有证据表明任何反应中存在分子内 C-H 插入类似的α-重氮-β-氧代砜。使用三氟甲磺酸铜(II) (5 mol%) 可以分离出一系列炔磺酰胺（产率高达 12%）和烯胺（产率高达 64%）。使用氯化铜(II) (5 mol%)还导致形成α-卤代磺酰胺；使用化学计量的氯化铜(II)/溴化铜(II)可以轻松地将β-酮磺酰胺卤化形成α-卤代磺酰胺（产率高达63%）。
• New antifilarial agents. 1. Epoxy sulfonamides and ethynesulfonamides
  作者：Marie Josephe Brienne、Daniel Varech、Martine Leclercq、Jean Jacques、Nathalie Radembino、Christine Dessalles、Georges Mahuzier、Chantal Gueyouche、Christian Bories

  DOI：10.1021/jm00395a010

  日期：1987.12

  Two series of 2-substituted 1,2-epoxyethanesulfonamides 2 and ethynesulfonamides 5 were synthesized and evaluated for their antifilarial activity. The trans epoxides 2T were stereospecifically prepared by a Darzens reaction between aldehydes and halomethanesulfonamides. The cis isomers 2c were obtained from ethynesulfonamides 5 by semihydrogenation followed by KOCl epoxidation. 2-Substituted ethynesulfonamides 5 were synthesized from appropriate trans-ethenesulfonamides by a bromination/dehydrobromination sequence. These products, as well as several synthetic intermediates, were evaluated for antifilarial activity against Molinema dessetae either in vivo in its natural host, the rodent Proechimys oris, or in vitro by a new test using cultures of the infective larvae. Most of the epoxides 2T and acetylenic derivatives 5 bearing a 2-aryl substituent were active in vitro. Among these compounds, four epoxides 2T and one acetylenic derivative 5 showed marked macrofilaricidal activity in vivo without any microfilaricidal activity. The differences between the in vivo and in vitro results may be due, in part, to the low chemical stability of the epoxy sulfonamides 2T. Despite this limitation, the activities observed in this reliable animal model suggest further development and testing of both series 2T and 5 as macrofilaricides.
• LECLERCO, MARTINE;BRIENNE, MARIE-JOSEPHE, TETRAHEDRON LETT., 31,(1990) N7, C. 3875-3878
  作者：LECLERCO, MARTINE、BRIENNE, MARIE-JOSEPHE

  DOI：——

  日期：——
• BRIENE, MARIE-JOSEPHE;VARECH, DANIEL;LECLERCQ, MARTINE;JACQUES, JEAN;BADE+, J. MED. CHEM., 30,(1987) N 12, 2232-2239
  作者：BRIENE, MARIE-JOSEPHE、VARECH, DANIEL、LECLERCQ, MARTINE、JACQUES, JEAN、BADE+

  DOI：——

  日期：——