N-cyclopentylbenzenesulfonamide

• 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-cyclopentylbenzenesulfonamide
• 化学式: C₁₁H₁₅NO₂S
• mdl: MFCD00593338
• 分子量: 225.312
• InChiKey: DMLOAFWBQNEOJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.454
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-benzenesulfonyl-N-benzylcyclopentylamine 在 Oxone 、 potassium bromide 作用下， 以 硝基甲烷 为溶剂， 反应 24.0h， 以65%的产率得到N-cyclopentylbenzenesulfonamide
  参考文献：
  名称：

  Oxidative Debenzylation of N-Benzyl Amides and O-Benzyl Ethers Using Alkali Metal Bromide

  摘要：

  The oxidative debenzylation of N-benzyl amides and O-benzyl ethers was promoted with high efficiency by a bromo radical formed through the oxidation of bromide from alkali metal bromide under mild conditions. This reaction provided the corresponding amides from N-benzyl amides and carbonyl compounds from O-benzyl ethers in high yields.

  DOI：

  10.1021/ol501703y

文献信息

• Expedient Synthesis of Sulfinamides from Sulfonyl Chlorides
  作者：Michael Harmata、Pinguan Zheng、Chaofeng Huang、Maria G. Gomes、Weijiang Ying、Kanok-On Ranyanil、Gayatri Balan、Nathan L. Calkins

  DOI：10.1021/jo062296i

  日期：2007.1.1

  Sulfinamides were synthesized from sulfonyl chlorides using a procedure involving in situ reduction of sulfonyl chlorides. The reaction is broad in scope and easy to perform.

  使用涉及原位还原磺酰氯的方法，由磺酰氯合成亚磺酰胺。该反应范围广且易于进行。
• PTAB mediated open air synthesis of sulfonamides, thiosulfonates and symmetrical disulfanes
  作者：Debayan Sarkar、Manoj Kumar Ghosh、Nilendri Rout

  DOI：10.1016/j.tetlet.2018.05.017

  日期：2018.6

  A facile methodology has been described which has successfully simplified the generation of sulfonamides, thiosulfonates and symmetric disulfanes. This “trio” of reactions occur in an open air metal free atmosphere and has also been scaled up to grams making it suitable for commercialization. The reactions also have been successfully carried out with asymmetric variants, thus contributing to the chiral

  已经描述了一种简便的方法，该方法已成功简化了磺酰胺，硫代磺酸盐和对称二硫烷的生成。这种“三重”反应发生在无金属的露天气氛中，并且也已按比例放大至克，使其适合商业化。该反应还已经成功地用不对称变体进行，因此有助于手性库。用户友好的“三重奏”能够轻松生成这些多用途的硫类似物，并且所采用的反应条件反映了经济状况。
• Sulfonamide Synthesis through Electrochemical Oxidative Coupling of Amines and Thiols
  作者：Gabriele Laudadio、Efstathios Barmpoutsis、Christiane Schotten、Lisa Struik、Sebastian Govaerts、Duncan L. Browne、Timothy Noël

  DOI：10.1021/jacs.9b02266

  日期：2019.4.10

  continuous development of novel and efficient synthetic methods to access these functional groups. Herein, we report an environmentally benign electrochemical method which enables the oxidative coupling between thiols and amines, two readily available and inexpensive commodity chemicals. The transformation is completely driven by electricity, does not require any sacrificial reagent or additional catalysts

  磺酰胺是药物和农用化学品中的关键基序，推动了对获取这些官能团的新型有效合成方法的不断开发。在此，我们报告了一种环境友好的电化学方法，该方法可以实现硫醇和胺之间的氧化偶联，这两种容易获得且价格低廉的商品化学品。转化完全由电力驱动，不需要任何牺牲试剂或额外的催化剂，只需5分钟即可完成。氢气在对电极处作为良性副产物形成。由于反应条件温和，该反应显示出广泛的底物范围和官能团兼容性。
• One-Pot Synthesis of Sulfonamides from Sodium Sulfinates and Amines via Sulfonyl Bromides
  作者：Jie Yan、Sixue Wu、Yikun Zhang、Min Zhu

  DOI：10.1055/s-0036-1588298

  日期：——

  a new and convenient procedure has been developed for the preparation of sulfonamides from sodium sulfinates and amines with ( n -C 4 H 9 ) 4 NBr as bromine source and m -chloroperbenzoic acid as oxidant. This S–N bond formation reaction proceeds efficiently via sulfonyl bromides under neutral conditions to afford the corresponding sulfonamides in good yields at room temperature.

  开发了一种新的方便的方法，用于以 (n -C 4 H 9 ) 4 NBr 为溴源，间氯过苯甲酸为氧化剂，由亚磺酸钠和胺类制备磺胺类药物。这种 S-N 键形成反应在中性条件下通过磺酰溴有效地进行，以在室温下以良好的收率提供相应的磺酰胺。
• Synthesis of sulfonamides promoted by alkyl iodide via a hypervalent iodine intermediate
  作者：Zhongshi Zhou、Xuehan He

  DOI：10.1080/10426507.2019.1686378

  日期：2020.4.2

  amount of m-chloroperbenzoic acid as oxidant and a catalytic amount of 1-iodopropane provides the corresponding sulfonamides in good yields under mild reaction conditions. In this protocol, 1-iodopropane is first oxidized by m-chloroperbenzoic acid into the corresponding hypervalent iodine intermediate iodosylpropane, which is highly unstable and decomposes at once to form hypoiodous acid. Then, the

  摘要 开发了一种以亚磺酸钠和胺为原料制备磺胺类药物的新方法。化学计算量的间氯过苯甲酸作为氧化剂和催化量的 1-碘丙烷在温和的反应条件下以良好的产率提供相应的磺酰胺。在该协议中，1-碘丙烷首先被间氯过苯甲酸氧化成相应的高价碘中间体碘基丙烷，该中间体极不稳定，会立即分解形成次碘酸。然后，生成的活性次碘酸与亚磺酸钠和胺的以下反应产生相应的磺胺。图形概要