N¹,N¹-dimethyl-N²-4-chlorophenylsulfonylformamidine | 29619-30-5

• 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: N¹,N¹-dimethyl-N²-4-chlorophenylsulfonylformamidine
• 英文别名: N,N-dimethyl-N'-<(4-chlorophenyl)sulfonyl>formamidine；N′-(4-chlorophenylsulfonyl)-N,N-dimethylformimidamide；4-chloro-N-[(dimethylamino)methylidene]benzenesulfonamide；N'-(4-chlorophenylsulfonyl)-N,N-dimethylformimidamide；N,N-dimethyl-N'-(4-chlorophenylsulfonyl)formimidamide；N,N-dimethyl-N'-4-chlorobenzenesulfonylformamidine；N'-(4-chlorophenyl)sulfonyl-N,N-dimethylmethanimidamide
• CAS: 29619-30-5
• 化学式: C₉H₁₁ClN₂O₂S
• 分子量: 246.718
• InChiKey: XUCBLSSGWYJQIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  58.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N,N-dichloro-4-chlorobenzenesulfonamide 反应 9.0h， 生成 N¹,N¹-dimethyl-N²-4-chlorophenylsulfonylformamidine
  参考文献：
  名称：

  Mirskova, A. N.; Levkovskaya, G. G.; Bryuzgin, A. A., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 1.2, p. 119 - 125

  摘要：

  DOI：

文献信息

• Topically active carbonic anhydrase inhibitors. 4. [(Hydroxyalkyl)sulfonyl]benzene and [(hydroxyalkyl)sulfonyl]thiophenesulfonamides
  作者：Kenneth L. Shepard、Samuel L. Graham、Ronald J. Hudcosky、Stuart R. Michelson、Thomas H. Scholz、Harvey Schwam、Anthony M. Smith、John M. Sondey、Kim M. Strohmaier

  DOI：10.1021/jm00114a020

  日期：1991.10

  active carbonic anhydrase inhibitor. Recent results from several research groups indicate that considerable progress has been made toward this objective. In this report, we present the design and synthesis of (hydroxyalkyl)sulfonyl-substituted benzene- and thiophenesulfonamides. These compounds exhibit inhibition of carbonic anhydrase II in the nanomolar range and lower intraocular pressure in the

  几十年来，治疗原发性开角型青光眼的诱人目标一直是开发局部活性的碳酸酐酶抑制剂。几个研究小组的最新结果表明，朝着这个目标已经取得了相当大的进步。在这份报告中，我们介绍了（羟烷基）磺酰基取代的苯-和噻吩磺酰胺的设计和合成。在局部滴注后，这些化合物在纳摩尔浓度范围内表现出对碳酸酐酶II的抑制作用，并且在经α-胰凝乳蛋白酶处理的高眼压性高血压兔模型中具有较低的眼内压。
• A Novel Synthesis of N-Sulfonylformamidines from N-Sulfonyl­sulfonamides
  作者：Hakjune Rhee、Yuri Jeong、Jaeyoung Ban、Minkyung Lim

  DOI：10.1055/s-0036-1591936

  日期：2018.5

  p-toluenesulfonyl chloride (TsCl) and N,N -disubstituted formamides. In this reaction, it was expected that mixing TsCl with the N,N-disubstituted formamide would generate an iminium salt (Vilsmeier reagent). The reaction avoids the use of metal catalysts and hazardous reagents, and the desired N-sulfonylformamidines were obtained in 60% to quantitative yields. N-Sulfonylformamidines were synthesized from N-sulfonylsulfonamides

  ‡这些作者对这项工作做出了同等的贡献 抽象的 Ñ -Sulfonylformamidines从合成Ñ -sulfonylsulfonamides通过与反应p甲苯磺酰氯（的TsCl）和Ñ，ñ -二取代的甲酰胺。在该反应中，预期将TsCl与N，N-二取代的甲酰胺混合将产生亚胺盐（Vilsmeier试剂）。该反应避免了使用金属催化剂和有害试剂，并且以60％至定量收率获得了所需的N-磺酰基甲am。 Ñ -Sulfonylformamidines从合成Ñ -sulfonylsulfonamides通过与反应p甲苯磺酰氯（的TsCl）和Ñ，ñ -二取代的甲酰胺。在该反应中，预期将TsCl与N，N-二取代的甲酰胺混合将产生亚胺盐（Vilsmeier试剂）。该反应避免了使用金属催化剂和有害试剂，并且以60％至定量收率获得了所需的N-磺酰基甲am。
• Otherwise inert reaction of sulfonamides/carboxamides with formamides via proton transfer-enhanced reactivity
  作者：Zaihai Niu、Shaoxia Lin、Zhiyong Dong、Hao Sun、Fushun Liang、Jingping Zhang

  DOI：10.1039/c3ob27351b

  日期：——

  NBS-mediated addition–elimination reaction of sulfonamides/carboxamides and formamides afforded N-sulfonylamidines and N-formylarylamides, respectively, depending on the different mechanism of elimination. Hydrogen bond-induced proton transfer leads to enhanced reactivities and was proposed as the key driving force for the reaction to take place. The protocol demonstrates the possibility of constructing chemical bonds based on a proton transfer strategy induced by noncovalent hydrogen bond interaction.

  NBS介导的磺胺/羧酰胺和甲酰胺的加成-消除反应分别提供了N-磺酰亚胺和N-甲酰芳基酰胺，这取决于不同的消除机理。氢键诱导的质子转移导致反应活性增强，并被认为是反应发生的关键驱动力。该方案展示了基于非共价氢键相互作用诱导的质子转移策略构建化学键的可能性。
• Metal- and solvent-free synthesis of N-sulfonylformamidines
  作者：Nisha Chandna、Navneet Chandak、Pawan Kumar、Jitander K. Kapoor、Pawan K. Sharma

  DOI：10.1039/c3gc40797g

  日期：——

  A solvent-free green synthesis of N-sulfonylformamidines is reported via the direct condensation of N,N-dimethylformamide dimethyl acetal (DMF-DMA) and sulfonamide derivatives at room temperature. The described method avoids the use of metal catalysts as well as hazardous solvents, which are not permitted for pharmaceutical manufacture, for the reactions or isolation of products. Hence, the current work presents a fast and efficient alternative to earlier reported methods. The mild nature of the procedure is demonstrated by varied functional group tolerance.

  报道了一种无溶剂的绿色合成N-磺酰基甲酰胺的方案，通过在室温下直接冷凝N,N-二甲基甲酰胺二甲基缩醛(DMF-DMA)和磺酰胺衍生物。该方法避免了使用金属催化剂以及对药物生产不允许的危险溶剂，从而用于反应或产品的分离。因此，目前的工作提供了一种比之前报道的方法更快速高效的替代方案。该程序的温和特性通过不同功能团的耐受性得到了验证。
• Gross,H.; Costisella,B., Justus Liebigs Annalen der Chemie, 1971, vol. 750, p. 44 - 52
  作者：Gross,H.、Costisella,B.

  DOI：——

  日期：——