rac-4-methyl-N-(pentan-2-yl)benzenesulfonamide

• 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: rac-4-methyl-N-(pentan-2-yl)benzenesulfonamide
• 英文别名: 4-methyl-N-(pentan-2-yl)benzenesulfonamide；N-(1-methylbutyl)-p-toluenesulfonamide；4-methyl-N-pentan-2-ylbenzenesulfonamide
• 化学式: C₁₂H₁₉NO₂S
• 分子量: 241.354
• InChiKey: ODMWZCBRHGGIGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  rac-4-methyl-N-(pentan-2-yl)benzenesulfonamide 在 碘苯二乙酸 、 碘 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以65%的产率得到2-methyl-1-tosylpyrrolidine
  参考文献：
  名称：

  Chemoselective Intramolecular Functionalization of Methyl Groups in Nonconstrained Molecules Promoted by N-Iodosulfonamides

  摘要：

  Mechanistic evidence observed in Hofmann-Loffler-Freytag-type reactions has been crucial to achieve the chemoselective functionalization of methyl groups under mild conditions. Radical-mediated methyl iodination and subsequent oxidative deiodination are the key steps in this functionalization, where iodine chemistry has a pivotal role on the formation of the C-N bond. The concepts of single hydrogen atom transfer (SHAT) and multiple hydrogen atom transfer (MHAT) are introduced to describe the observed chemoselectivity.

  DOI：

  10.1021/acs.orglett.5b00866
• 作为产物：
  描述：

  4-氨基戊烷-2-醇 在 三正丁基氢锡 、 三乙胺 作用下， 以 二氯甲烷 、 xylene 为溶剂， 反应 36.25h， 生成 rac-4-methyl-N-(pentan-2-yl)benzenesulfonamide
  参考文献：
  名称：

  从硫到碳的立体选择性自由基芳基迁移反应

  摘要：

  报道了从磺酸盐和磺酰胺中的硫到 C 中心自由基的立体选择性芳基迁移反应。从硫到不同取代的 C 中心自由基的 1,5-芳基迁移可以以高产率和选择性进行。官能化的芳基也可以通过这种新方法转移。提出了解释反应立体化学结果的模型，并讨论了该反应的一些机理方面。从亚磺酸盐中的硫到碳自由基的芳基迁移反应效率较低，并且根本没有观察到芳基亚砜中的相应迁移。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

  DOI：

  10.1002/1099-0690(200208)2002:16<2742::aid-ejoc2742>3.0.co;2-r

文献信息

• Flow synthesis and biological activity of aryl sulfonamides as selective carbonic anhydrase IX and XII inhibitors
  作者：Emiliano Rosatelli、Andrea Carotti、Mariangela Ceruso、Claudiu T. Supuran、Antimo Gioiello

  DOI：10.1016/j.bmcl.2014.05.086

  日期：2014.8

  A series of secondary and tertiary aryl sulfonamides were synthesized under flow conditions and evaluated for their ability to selectively inhibit tumor-associated carbonic anhydrase isoforms IX and XII. The tested compounds revealed to be highly potent CA IX inhibitors in nanomolar range, and to inhibit CA XII activity with different ranks of potencies. Remarkably, 4-methyl-N-phenyl-benzenesulfonamide

  在流动条件下合成了一系列仲和叔芳基磺酰胺，并评估了它们选择性抑制肿瘤相关的碳酸酐酶同工型IX和XII的能力。测试的化合物显示出在纳摩尔范围内是高效的CA IX抑制剂，并以不同的效力等级抑制CA XII活性。值得注意的是，4-甲基-N-苯基-苯磺酰胺是一种选择性的纳摩尔CA IX抑制剂，IC 50为90 nM。
• Copper-Catalyzed Hydrogen Atom Transfer and Aryl Migration Strategy for the Arylalkylation of Activated Alkenes
  作者：Xi Chen、Qiang Wang、Zhe Zhang、Zhi-Jie Niu、Wei-Yu Shi、Xiao-Ping Gong、Rui-Qiang Jiao、Ming-Hui Gao、Xue-Yuan Liu、Yong-Min Liang

  DOI：10.1021/acs.orglett.2c01427

  日期：2022.6.24

  arylalkylation of activated alkenes via hydrogen-atom transfer and aryl migration strategy. The reaction was carried out through a radical-mediated continuous migration pathway using N-fluorosulfonamides as the alkyl source. The primary, secondary, and tertiary alkyl radicals formed by intramolecular hydrogen-atom transfer proceeded smoothly. This methodology is an efficient approach for the synthesis of various

  在此，我们描述了通过氢原子转移和芳基迁移策略铜催化的活化烯烃芳基烷基化。该反应通过自由基介导的连续迁移途径进行，使用N-氟磺酰胺作为烷基源。分子内氢原子转移形成的伯、仲、叔烷基自由基进行得很顺利。该方法是合成具有季碳中心的各种酰胺衍生物的有效方法，具有良好的收率和高区域选择性。
• Copper-Catalyzed, Interrupted Remote Fluoromethylthiolation of Unactivated C(sp3)-H Bonds
  作者：Fan Yu、Wengui Wang、Shoufeng Wang

  DOI：10.1021/acs.orglett.4c00336

  日期：2024.3.15

  An efficient copper-catalyzed selective fluoromethylthiolation of an inert δ-C(sp3)–H bond in sulfonamides was reported. In the presence of a copper catalyst and PhSO2SRf, the radical generated through 1,5-hydrogen atom transfer (HAT) was sufficiently trapped by PhSO2SRf, instead of copper, which was prevalent in metal-catalyzed radical-relay processes, incorporating a fluoromethylthio group into molecules

  报道了磺酰胺中惰性 δ-C(sp 3 )-H 键的高效铜催化选择性氟甲基硫基化反应。在铜催化剂和PhSO 2 SR f的存在下，通过1,5-氢原子转移（HAT）产生的自由基被PhSO 2 SR f充分捕获，而不是金属催化自由基继电器中普遍存在的铜。过程，将氟甲硫基结合到分子中。通用的底物范围和温和的条件使该方法在医药和农用化学品中具有广泛的潜在应用。
• Indium Promotes Direct Sulfonamidation of Unactivated Alcohols
  作者：Yaoyao Ban、Yuhan Liu、Shuwei Zhang、Xiaodong Jia、Pan Gao、Yu Yuan

  DOI：10.1021/acs.joc.4c00311

  日期：2024.5.3

  An improved protocol has been developed for the direct sulfonamidation of unactivated alkyl alcohols using In(OTf)3 as a Lewis acid catalyst. Although the established methods using Lewis or Brønsted acids have been well-studied for the direct functionalization of alcohols, their substrate scope mainly focuses on the π-activated alcohols. In this reaction, unactivated aliphatic alcohols were evaluated

  开发了一种改进的方案，用于使用 In(OTf) 3作为路易斯酸催化剂对未活化的烷基醇进行直接磺酰胺化。尽管使用路易斯酸或布朗斯台德酸的既定方法已针对醇的直接官能化进行了深入研究，但其底物范围主要集中在 π 活化醇上。在此反应中，对未活化的脂肪醇进行了评估，并以良好至优异的收率提供了所需的磺酰胺产物。
• Building a Sulfonamide Library by Eco-Friendly Flow Synthesis
  作者：Antimo Gioiello、Emiliano Rosatelli、Michela Teofrasti、Paolo Filipponi、Roberto Pellicciari

  DOI：10.1021/co400012m

  日期：2013.5.13

  A rapid and eco-friendly synthesis of a sulfonamide library under flow conditions is described. The study illustrates an efficient, safe, and easily scalable preparation of sulfonamides by use of a meso-reactor apparatus, thus demonstrating the impact of flow technologies within drug discovery. Waste minimization, employment of green media, and nontoxic reactants are achieved by the optimization of the flow setup and experimental protocol designed to sequentially synthesize primary, secondary, and tertiary sulfonamides. Isolation of the products involves only extraction and precipitation affording pure compounds in good to high yields without further purification for biological evaluation.