N-(1-ethylhexyl)-4-methylbenzenesulfonamide | 220901-34-8

• 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-(1-ethylhexyl)-4-methylbenzenesulfonamide
• 英文别名: N-(1-ethylhexyl)-p-toluenesulfonamide；N-(3-octyl)-p-toluenesulfonamide；N-tosyl-3-aminooctane；N-tosyl-3-octanamine；Benzenesulfonamide, N-(1-ethylhexyl)-4-methyl-；4-methyl-N-octan-3-ylbenzenesulfonamide
• CAS: 220901-34-8
• 化学式: C₁₅H₂₅NO₂S
• 分子量: 283.435
• InChiKey: IPVUDTJGOZVZNT-UHFFFAOYSA-N

物化性质

• 沸点：
  391.8±35.0 °C(Predicted)
• 密度：
  1.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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-(p-toluenesulfonyl)-2-bromomethylaziridine 在 CuCN 作用下， 以 乙醚 为溶剂， 反应 12.0h， 生成 N-(1-ethylhexyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Ring opening reactions of 1-arenesulfonyl-2-(bromomethyl)aziridines

  摘要：

  The reactivity of 1-arenesulfonyl-2-(bromomethyl)aziridines with respect to lithium dialkylcyanocuprates and lithium dialkylcuprates (Gilman reagents) has been evaluated for the first time, pointing to the conclusion that these substrates can be applied successfully as synthetic equivalents for the 2-aminopropane dication synthon towards 2-alkylaziridines and alpha-branched N-tosylamides in good yields. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.059

文献信息

• Gold(I)-Catalyzed Intra- and Intermolecular Hydroamination of Unactivated Olefins
  作者：Junliang Zhang、Cai-Guang Yang、Chuan He

  DOI：10.1021/ja053864z

  日期：2006.2.1

  Ph3PAuOTf catalyzes efficient intra- and intermolecular hydroamination of unactivated olefins with sulfonamides.

  Ph3PAuOTf 用磺酰胺催化未活化烯烃的有效分子内和分子间加氢胺化。
• Gold<i>versus</i>Silver-Catalyzed Intermolecular Hydroaminations of Alkenes and Dienes
  作者：Xavier Giner、Carmen Nájera、Gábor Kovács、Agustí Lledós、Gregori Ujaque

  DOI：10.1002/adsc.201100478

  日期：2011.12

  Comparative studies about the hydroamination of unactivated alkenes and dienes catalyzed by either cationic gold(I) triphenyl phosphite complexes or silver salts were performed using sulfonamides, anilines and carbamates as nucleophiles. Gold-catalyzed reactions generally, need lower loadings than those carried out with silver salts. Simple alkenes react only with sulfonamides and weak aromatic amines

  使用磺酰胺，苯胺和氨基甲酸酯作为亲核试剂，对阳离子金（I）亚磷酸三苯酯配合物或银盐催化的未活化烯烃和二烯的加氢胺化进行了比较研究。与银盐进行的反应相比，金催化的反应通常需要较低的负载量。简单烯烃仅与磺酰胺和弱芳族胺（例如对位）反应-硝基苯胺，而对于共轭二烯，也可以使用氨基甲酸酯。碳-碳双键异构化仅在使用金的情况下才能观察到，与使用三氟甲磺酸相似，在相同情况下可提供区域异构体产物的混合物。银催化的加氢胺化反应除苯乙烯外均不能用于末端烯烃。共轭二烯可以在85°C的甲苯中或室温下的二氯甲烷中进行氨化。非共轭的1,4-和1,5-二烯经历两次加氢胺化反应，生成饱和的N-甲苯磺酸化杂环胺。已对银（I）催化的加氢胺化过程的催化循环进行了计算分析，类似于金（I）催化的过程。 ，尽管有一些显着差异。
• Zirconium-Catalyzed Intermolecular Hydroamination of Unactivated Olefins
  作者：Li-Wen Xu、Chun-Gu Xia、Lei Yang、Wei Zhou、Yue-Hua Gao、Wei Sun

  DOI：10.1055/s-0028-1088151

  日期：2009.4

  Highly efficient hydroamination reactions of sulfonamides, carboxamides, and carbamates with unactivated olefins catalyzed by simple and inexpensive zirconium salts under mild reaction conditions were presented for the practical preparation of various amines. These processes gave good to excellent yields of the addition products in Markovnikov addition fashion.

  提出了在温和的反应条件下，在温和的反应条件下，磺酰胺、甲酰胺和氨基甲酸酯与未活化烯烃的高效加氢胺化反应，用于实际制备各种胺。这些方法以马尔科夫尼科夫加成方式提供了良好至极好的加成产物的产率。
• Mono- vs. Dinuclear Gold-Catalyzed Intermolecular Hydroamidation
  作者：Juan M. Serrano-Becerra、Alexander F. G. Maier、Sandra González-Gallardo、Eric Moos、Christoph Kaub、Maximilian Gaffga、Gereon Niedner-Schatteburg、Peter W. Roesky、Frank Breher、Jan Paradies

  DOI：10.1002/ejoc.201402068

  日期：2014.7

  Mono- and dinuclear gold catalysts were investigated in the intermolecular hydroamidation of olefins. Upon activation of [Ph3PAuCl] and [xantphos(AuCl)2] with various silver salts (AgOTf, Ag[BF4], and Ag[SbF6]), diverging reactivity of the resulting cationic gold complexes was observed. It was found that both the binding ability of the counterion and the solvent have a significant impact on the reactivity

  在烯烃的分子间加氢酰胺化中研究了单核和双核金催化剂。在用各种银盐（AgOTf、Ag[BF4] 和 Ag[SbF6]）活化 [Ph3PAuCl] 和 [xantphos(AuCl)2] 后，观察到所得阳离子金配合物的不同反应性。发现抗衡离子和溶剂的结合能力对单核和双核复合物的反应性都有显着影响。
• Hydroamination and Hydroalkoxylation Catalyzed by Triflic Acid. Parallels to Reactions Initiated with Metal Triflates
  作者：Devon C. Rosenfeld、Shashank Shekhar、Akihiro Takemiya、Masaru Utsunomiya、John F. Hartwig

  DOI：10.1021/ol061174+

  日期：2006.9.1

  Intermolecular additions of the O-H bonds of phenols and alcohols and the N-H bonds of sulfonamides and benzamide to olefins catalyzed by 1 mol % of triflic acid and studies to define the relationship between these reactions and those catalyzed by metal triflates are reported. Cyclization of an alcohol containing pendant monosubstituted and trisubstituted olefins catalyzed by either triflic acid or metal triflates form products from addition to the more substituted olefin, and additions of tosylamide catalyzed by triflic acid or metal triflates form indistinguishable ratios of the two N-alkyl sulfonamides.