N,N-diethylthiophene-2-sulfonamide | 41895-11-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N,N-diethylthiophene-2-sulfonamide
• CAS: 41895-11-8
• 化学式: C₈H₁₃NO₂S₂
• mdl: MFCD02135295
• 分子量: 219.329
• InChiKey: JOYQKVKJPNYDOA-UHFFFAOYSA-N

物化性质

• 沸点：
  321.8±34.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  74
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-diethylthiophene-2-sulfonamide 、 4-溴苯甲酰苯 在 potassium acetate 、 palladium diacetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 16.0h， 以81%的产率得到5-(4-benzoylphenyl)thiophene-2-sulfonic acid diethylamide
  参考文献：
  名称：

  Palladium-Catalyzed Direct Arylation of Thiophenes Bearing SO₂R Substituents

  摘要：

  The palladium-catalyzed direct arylation of SO2R-substituted thiophene derivatives was found to proceed regioselectively at CS and in high yields using a variety of aryl bromides and as low as 0.5-0.1 mol % of phosphine-free Pd(OAc)(2) as the catalyst. For these reactions, sulfonyls, sulfonamides, or even a sulfonic ester as the thiophene substituents were successfully employed.

  DOI：

  10.1021/jo200918n
• 作为产物：
  描述：

  2-噻吩磺酰氯 、 N,N-二乙基苄胺 在 calcium hydride 、 methyl violet 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以72%的产率得到N,N-diethylthiophene-2-sulfonamide
  参考文献：
  名称：

  可见光促进叔苄胺的去苄基磺酰化

  摘要：

  描述了叔苄胺的可见光光催化脱苄基磺酰化，以高收率提供了一系列磺酰胺。该操作简单的转化显示出高官能团相容性和广泛的底物范围。

  DOI：

  10.1002/ejoc.202100144

文献信息

• [EN] PIPERAZINE DERIVATIVES USEFUL FOR THE TREATMENT OF GASTROINTESTINAL DISORDERS<br/>[FR] DERIVES DE PIPERAZINE CONVENANT POUR LE TRAITEMENT DE TROUBLES GASTRO-INTESTINAUX
  申请人：GLAXO GROUP LTD

  公开号：WO2006010629A1

  公开（公告）日：2006-02-02

  The invention provides compounds of formula (I) or pharmaceutically acceptable salts thereof, wherein Ra, Rb, Rc, Rd, Re, Rf and Y are as defined in the specification. The compounds are partial or full agonists at the growth hormone secretagogue (GHS) receptors . Pharmaceutical compositions comprising the compounds, methods of preparing the compounds, uses of the compounds and methods involving the compounds are also provided.

  这项发明提供了式（I）的化合物或其药用盐，其中Ra、Rb、Rc、Rd、Re、Rf和Y如规范中所定义。这些化合物是生长激素分泌素（GHS）受体的部分或全激动剂。还提供了包括这些化合物的药物组合物、制备这些化合物的方法、这些化合物的用途以及涉及这些化合物的方法。
• Synthesis of sulfonamides via copper-catalyzed oxidative C–N bond cleavage of tertiary amines
  作者：Jing Ji、Zhengyi Liu、Ping Liu、Peipei Sun

  DOI：10.1039/c6ob01208f

  日期：——

  A copper-catalyzed coupling reaction of sulfonyl chlorides with tertiary amines via the oxidative C–N bond cleavage of tertiary amines was developed. Sulfonamides were synthesized using this strategy in moderate to good yields. The reaction was applicable to various tertiary amines, as well as sulfonyl chlorides.

  开发了铜催化的磺酰氯与叔胺通过叔胺的氧化C–N键裂解的偶联反应。使用该策略以中等至良好的产率合成了磺酰胺。该反应适用于各种叔胺以及磺酰氯。
• Charge-Transfer Complex Promoted Regiospecific C−N Bond Cleavage of Vicinal Tertiary Diamines
  作者：Ying Fu、Qin-Shan Xu、Chun-Zhao Shi、Zhengyin Du、Caiqin Xiao

  DOI：10.1002/adsc.201800591

  日期：2018.9.17

  A catalyst‐free, charge‐transfer complex promoted coupling of sulfonyl chlorides with vicinal tertiary diamines to generate sulfonamides is presented. Mechanistic studies showed that these reactions are proceeded via charge transfer of vicinal tertiary diamines to sulfonyl chlorides, forming the unstable sulfonyl quaternary ammonium like complexes which induced the regiospecific intramolecular C−N

  提出了一种无催化剂，电荷转移的复合物，可促进磺酰氯与邻位叔二胺的偶联，从而生成磺酰胺。机理研究表明，这些反应是通过将邻位叔二胺电荷转移至磺酰氯而进行的，形成了不稳定的磺酰基季铵盐状复合物，从而诱导了邻位叔二胺的区域特异性分子内C-N键裂解。
• NaI-Catalyzed Oxidative Amination of Aromatic Sodium Sulfinates: Synergetic Effect of Ethylene Dibromide and Air as Oxidants
  作者：Ying Fu、Quan-Zhou Li、Qin-Shan Xu、Helmut Hügel、Ming-Peng Li、Zhengyin Du

  DOI：10.1002/ejoc.201801386

  日期：2018.12.31

  A novel NaI-catalyzed oxidative amination of sodium sulfinates, employing both ethylene dibromide (EDB) and air as the oxidants, is described. EDB was first demonstrated to be a promising mild organic oxidant that in air, converted NaI into molecular iodine to promote the cross-coupling reactions of aromatic sodium sulfinates with amines to produce arylsulfonamides. Mechanistic studies indicated that

  描述了一种使用二溴化乙烯 (EDB) 和空气作为氧化剂的新型 NaI 催化亚磺酸钠氧化胺化。EDB 首次被证明是一种有前途的温和有机氧化剂，它在空气中将 NaI 转化为分子碘，以促进芳族亚磺酸钠与胺的交叉偶联反应，生成芳基磺酰胺。机理研究表明，反应过程中可能涉及自由基途径。
• Double C–N bond cleavages of <i>N</i>-alkyl 4-oxopiperidinium salts: access to unsymmetrical tertiary sulfonamides
  作者：Ying Fu、Ming-Peng Li、Chun-Zhao Shi、Fang-Rong Li、Zhengyin Du、Congde Huo

  DOI：10.1039/c9ob02107h

  日期：——

  paper, regiospecific, double intraannular C–N bond cleavages of N-alkyl 4-oxopiperidinium salts are presented. The reaction sequence involves a charge-transfer complex, in situ formed between sulfonyl chloride and N-methylmorpholine, which induces S–Cl bond homolysis of sulfonyl chloride, yielding a reactive sulfonyl radical that further induces the double C–N bond cleavages of N-alkyl 4-oxopiperidinium

  在本文中，提出了N-烷基4-氧代哌啶鎓盐的区域特异性双环内C–N键裂解。反应顺序包括一个电荷转移络合物，原位磺酰氯和之间形成Ñ甲基吗啉，磺酰氯，其诱导S-Cl键均裂，产生反应性基团磺酰进一步诱导的双C-N键断裂ñ -烷基4-氧代哌啶鎓盐。如此产生的仲胺被磺酰氯捕获，得到所需的磺酰胺产物。该协议的关键特征是，在无金属和无氧化剂的条件下，一步切割了4-氧杂环哌啶环的两个环内C–N键。