N-(2-bromo-2-phenylethyl)-4-methylbenzenesulfonamide | 374067-59-1

• 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-(2-bromo-2-phenylethyl)-4-methylbenzenesulfonamide
• 英文别名: 1-bromo-1-phenyl-2-(p-toluenesulfonylamino)ethane；1-bromo-1-phenyl-2-(p-toluenesulfonamido)ethane；1-phenyl-1-bromo-2-(p-toluenesulfonamido)ethane；2-bromo-2-phenyl-N-tosylethanamine；N-(β-bromo-phenethyl)-toluene-4-sulfonamide；N-(β-Brom-phenaethyl)-toluol-4-sulfonamid
• CAS: 374067-59-1
• 化学式: C₁₅H₁₆BrNO₂S
• 分子量: 354.268
• InChiKey: IJVRTFORADAUCS-UHFFFAOYSA-N

物化性质

• 熔点：
  111 °C
• 沸点：
  463.3±55.0 °C(Predicted)
• 密度：
  1.431±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  N-(2-bromo-2-phenylethyl)-4-methylbenzenesulfonamide 在 戊醇 、 sodium 作用下， 生成 2-苯乙胺
  参考文献：
  名称：

  The Addition of N-Haloamides to Olefins

  摘要：

  DOI：

  10.1021/ja01267a057
• 作为产物：
  描述：

  (R)-2-phenyl-N-tosylaziridine 在 zinc dibromide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-(2-bromo-2-phenylethyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  卤化锌（II）对N-甲苯磺酰氮丙啶区域选择性开放的有效途径

  摘要：

  描述了N-甲苯磺酰基氮丙啶与二卤化锌（ZnX 2，X ＝ Cl，Br，I）的区域和立体选择性开环的有效途径。根据溶剂和卤化锌（II）的不同，有选择地以良好至极好的收率获得β-卤代胺或咪唑啉。

  DOI：

  10.1016/j.tetlet.2005.04.006

文献信息

• Double Functionalization of Styrenes by Cu-Mediated Assisted Tandem Catalysis
  作者：Daichi Kawauchi、Hirofumi Ueda、Hidetoshi Tokuyama

  DOI：10.1002/ejoc.201900088

  日期：2019.3.14

  Various C–C and C‐X bonds could be formed by double functionalization of olefins featuring Cu‐mediated assisted tandem catalysis. Furthermore, one‐pot indoline syntheses with o‐bromostyrenes as an application could be achieved.

  通过具有铜介导的辅助串联催化作用的烯烃的双重官能化，可以形成各种C–C和C–X键。此外，可以实现与邻溴苯乙烯的一锅二氢吲哚合成。
• Regiospecific Three-Component Aminofluorination of Olefins via Photoredox Catalysis
  作者：Jia-Nan Mo、Wan-Lei Yu、Jian-Qiang Chen、Xiu-Qin Hu、Peng-Fei Xu

  DOI：10.1021/acs.orglett.8b01760

  日期：2018.8.3

  Direct visible-light-mediated aminofluorination of styrenes has been developed with high regioselectivity. Shelf-stable N-Ts-protected 1-aminopyridine salt was used as the nitrogen-radical precursor, and the commercially available hydrogen fluoride-pyridine was used as the nucleophilic fluoride source. The synthesis of an analogue of LY503430 was performed to demonstrate the synthetic value of this

  已经开发了具有高区域选择性的直接可见光介导的苯乙烯氨基氟化。将耐贮存的N -Ts保护的1-氨基吡啶盐用作氮自由基前体，并将可商购的氟化氢-吡啶用作亲核氟化物源。进行LY503430类似物的合成以证明该策略的合成价值。
• Atmosphere- and Temperature-Controlled Regioselective Aminobromination of Olefins
  作者：Wesley Zongrong Yu、Yi An Cheng、Ming Wah Wong、Ying-Yeung Yeung

  DOI：10.1002/adsc.201600821

  日期：2017.1.19

  A complete switch of regioselectivity in the aminobromination of olefins is realized from delicate changes in the reaction temperature from 25 °C to 40 °C and the atmosphere from air to argon, under catalyst‐free conditions. The resulting α‐bromoamides can be transformed easily to high‐value compounds (e.g., Clobenzorex). Mechanistic studies revealed that the reaction went through a radical pathway

  在无催化剂条件下，反应温度从25°C到40°C以及气氛从空气到氩气的微妙变化，可以实现烯烃氨基溴化中区域选择性的完全转换。所得的α-溴酰胺可轻松转化为高价值化合物（例如，氯苯并re）。机理研究表明，该反应经历了由原位生成的溴（甲苯磺酰基）胺（TsNHBr）控制的自由基途径。
• Rasta resin–triphenylphosphine oxides and their use as recyclable heterogeneous reagent precursors in halogenation reactions
  作者：Xuanshu Xia、Patrick H Toy

  DOI：10.3762/bjoc.10.143

  日期：——

  Heterogeneous polymer-supported triphenylphosphine oxides based on the rasta resin architecture have been synthesized, and applied as reagent precursors in a wide range of halogenation reactions. The rasta resin–triphenylphosphine oxides were reacted with either oxalyl chloride or oxalyl bromide to form the corresponding halophosphonium salts, and these in turn were reacted with alcohols, aldehydes, aziridines and epoxides to form halogenated products in high yields after simple purification. The polymer-supported triphenylphosphine oxides formed as a byproduct during these reactions could be recovered and reused numerous times with no appreciable decrease in reactivity.

  基于RASTA树脂架构的异质聚合物支承的氧化三苯基膦已经被合成，并应用于广泛的卤化反应中作为试剂前体。RASTA树脂-氧化三苯基膦与草酰氯或草酰溴反应，形成相应的卤化膦盐，这些卤化膦盐再与醇、醛、氮杂环丙烷和环氧乙烷反应，在简单纯化后以高收率形成卤代产物。在这些反应中形成的聚合物支承的氧化三苯基膦作为副产品，可以被回收并多次重复使用，且没有明显的活性下降。
• Transition Metal-Catalyzed Regio- and Stereoselective Aminobromination of Olefins with TsNH₂ and NBS as Nitrogen and Bromine Sources
  作者：Vinay V. Thakur、Siva Kumar Talluri、A. Sudalai

  DOI：10.1021/ol027530f

  日期：2003.3.1

  for aminohalogenation of olefins has been developed for the preparation of vicinal haloamine derivatives in high yields by using Cu, Mn, or V catalysts with p-toluenesulfonamide (TsNH(2)) and N-bromosuccinimide (NBS) as nitrogen and bromine sources, respectively. Unprecedented regio- and stereoselectivity (anti:syn > 99:1) toward the aminohalogenation process is shown for olefinic substrates as well

  [反应：见正文]已开发出一种新的烯烃氨基卤化合成方法，该方法可通过使用铜，锰或钒催化剂与对甲苯磺酰胺（TsNH（2））和N-溴代琥珀酰亚胺高产率制备邻位卤代胺衍生物（NBS）分别作为氮和溴源。对于烯烃底物以及过渡金属催化剂，显示出前所未有的对氨基卤化过程的区域选择性和立体选择性（反比：syn> 99：1）。