4-methyl-N-(3-oxobutyl)benzenesulfonamide | 82125-95-9

• 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: 4-methyl-N-(3-oxobutyl)benzenesulfonamide
• 英文别名: Benzenesulfonamide, 4-methyl-N-(3-oxobutyl)-
• CAS: 82125-95-9
• 化学式: C₁₁H₁₅NO₃S
• 分子量: 241.311
• InChiKey: NQPYXNZQRKEDAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-N-(3-oxobutyl)benzenesulfonamide 在 甲醇 、 sodium tetrahydroborate 作用下， 生成 N-(3-hydroxybutyl)-4-methylbenzene-1-sulfonamide
  参考文献：
  名称：

  中断 Barton-McCombie 反应：O-烷基硫代碳酸酯的水性脱氧三氟甲基化

  摘要：

  脂肪族系统的位点选择性三氟甲基化仍然是一个重要的挑战。这项工作描述了O-烷基硫代碳酸酯的光驱动、铜介导的三氟甲基化。该反应提供了广泛的官能团耐受性（例如，炔烃、烯烃、苯酚、游离醇、富电子和缺电子芳烃），从而为三氟甲基化提供正交性和实用性。提出了一种自由基有机金属机理。

  DOI：

  10.1021/acs.orglett.0c04039
• 作为产物：
  描述：

  1-(1-tosylaziridin-2-yl)ethanone 在 甲醇 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以95%的产率得到4-methyl-N-(3-oxobutyl)benzenesulfonamide
  参考文献：
  名称：

  Reduction of 2-Acylaziridines by Samarium(II) Iodide. An Efficient and Regioselective Route to .beta.-Amino Ketones and Esters

  摘要：

  DOI：

  10.1021/jo00126a005

文献信息

• PROCESS FOR THE SYNTHESIS OF KETONES FROM INTERNAL ALKENES
  申请人：CALIFORNIA INSTITUTE OF TECHNOLOGY

  公开号：US20140194604A1

  公开（公告）日：2014-07-10

  The present invention is directed to methods for oxidizing internal olefins to ketones. In various embodiments, each method comprising contacting an organic substrate, having an initial internal olefin, with a mixture of (a) a biscationic palladium salt; and (b) an oxidizing agent; dissolved or dispersed in a solvent system to form a reaction mixture, said solvent system comprising at least one C 2-6 carbon nitrile and optionally at least one secondary alkyl amide, said method conducted under conditions sufficient to convert at least 50 mol % of the initial internal olefin to a ketone, said ketone positioned on a carbon of the initial internal olefin. The transformation occurs at room temperature and shows wide substrate scope. Applications to the oxidation of seed oil derivatives and a bioactive natural product are described.

  本发明涉及将内烯烃氧化为酮的方法。在各种实施方式中，每种方法包括将具有初始内烯烃的有机底物与（a）双阳离子钯盐的混合物；和（b）氧化剂接触，溶解或分散在溶剂体系中形成反应混合物，所述溶剂体系包括至少一种C2-6碳腈和可选地至少一种次烷基酰胺，所述方法在足以将初始内烯烃的至少50摩尔％转化为酮的条件下进行，所述酮位于初始内烯烃的碳上。该转化在室温下发生，并显示出广泛的底物范围。描述了将其应用于种子油衍生物和生物活性天然产物的氧化。
• Regioselective Wacker Oxidation of Internal Alkenes: Rapid Access to Functionalized Ketones Facilitated by Cross-Metathesis
  作者：Bill Morandi、Zachary K. Wickens、Robert H. Grubbs

  DOI：10.1002/anie.201303587

  日期：2013.9.9

  Wacka wacka: The title reaction makes use of a wide range of directing groups (DG) to enable the highly regioselective oxidation of alkenes, and occurs predictably at the distal position. Both E and Z alkenes afford valuable functionalized ketones and cross‐metathesis was shown to facilitate the preparation of the starting materials. BQ=benzoquinone.

  Wacka wacka：标题反应利用了广泛的导向基团（DG）来实现烯烃的高度区域选择性氧化，并且可预测地发生在末端位置。既Ë和Ž 烯烃得到有价值官能酮和交叉复分解显示出促进起始原料的制备。BQ ＝苯醌。
• Regioselective Wacker-Type Oxidation of Internal Olefins in ^<i>t</i>BuOH Using Oxygen as the Sole Oxidant and ^<i>t</i>BuONO as the Organic Redox Cocatalyst
  作者：Qing Huang、Ya-Wei Li、Xiao-Shan Ning、Guo-Qing Jiang、Xiao-Wei Zhang、Jian-Ping Qu、Yan-Biao Kang

  DOI：10.1021/acs.orglett.9b04503

  日期：2020.2.7

  A regioselective Wacker-Tsuji oxidation of internal olefins in tBuOH has been developed using oxygen as the terminal oxidant and tert-butyl nitrite as the simple organic redox cocatalyst without the involvement of hazardous cocatalysts or harsh reaction conditions. A series of internal olefins bearing various functional groups can be oxidized to the corresponding substituted ketones in generally good

  使用氧气作为末端氧化剂，使用亚硝酸叔丁酯作为简单的有机氧化还原助催化剂，开发了tBuOH中内部烯烃的区域选择性Wacker-Tsuji氧化方法，而没有涉及危险的助催化剂或苛刻的反应条件。一系列带有各种官能团的内烯烃可以以高区域选择性的通常良好的收率被氧化成相应的取代的酮。
• Photocatalytic carbanion generation from C–H bonds – reductant free Barbier/Grignard-type reactions
  作者：Anna Lucia Berger、Karsten Donabauer、Burkhard König

  DOI：10.1039/c9sc04987h

  日期：——

  generation of carbanions from benzylic C–H bonds in a photocatalytic Grignard-type reaction. The combination of photo- and hydrogen atom transfer (HAT) catalysis enables the abstraction of a benzylic hydrogen atom, generating a radical intermediate. This radical is reduced in situ by the organic photocatalyst to a carbanion, which is able to react with electrophiles such as aldehydes or ketones, yielding homobenzylic

  我们报道了在光催化格利雅型反应中从苄基CH键生成碳负离子的氧化还原中性方法。光和氢原子转移（HAT）催化的结合使抽象的氢苄基原子，产生自由基中间体。该自由基被有机光催化剂原位还原成碳负离子，该碳负离子能够与亲电子试剂（如醛或酮）反应，生成均苄基仲和叔醇。
• Amino acid synthesis via ring opening of N-sulphonyl aziridine-2-carboxylate esters with organometallic reagents.
  作者：Jack E. Baldwin、Alan C. Spivey、Christopher J. Schofield、Joseph B. Sweeney

  DOI：10.1016/s0040-4020(01)87968-0

  日期：1993.7

  Nucleophilic ring opening of optically active N-sulphonyl aziridine-2-carboxylate esters with organometallic reagents has been investigated as a method of preparation of optically active amino acids.

  作为制备旋光氨基酸的方法，已经研究了旋光N-磺酰基氮丙啶-2-羧酸酯与有机金属试剂的亲核开环。