(E)-N-(1,3-di-p-tolylallyl)-4-methylbenzenesulfonamide | 1026688-79-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-N-(1,3-di-p-tolylallyl)-4-methylbenzenesulfonamide
• 英文别名: N-[(E)-1,3-bis(4-methylphenyl)prop-2-enyl]-4-methylbenzenesulfonamide
• CAS: 1026688-79-8
• 化学式: C₂₄H₂₅NO₂S
• 分子量: 391.534
• InChiKey: HIJIJBNANDICBA-SFQUDFHCSA-N

物化性质

• 沸点：
  566.5±60.0 °C(Predicted)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  (E)-N-(1,3-di-p-tolylallyl)-4-methylbenzenesulfonamide 在 1,10-菲罗啉 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以93%的产率得到1,3-二(4-甲基苯基)-1-丙酮
  参考文献：
  名称：

  Transition-Metal-Free Self-Hydrogen-Transferring Allylic Isomerization

  摘要：

  Phenanthroline and tert-butoxide have been established as powerful radical initiators in reactions such as the S(RN)1-type coupling reactions due to the cooperation of large heteroarenes and a special feature of tert-butoxide. The first phenanthroline-tert-butoxide-catalyzed transition-metal-free allylic isomerization is described. The resulting ketones are key intermediates for indenes. The control experiments rule out the base-promoted allylic anion pathway. The radical pathway is supported by experimental evidence that includes kinetic study, kinetic isotope effect, isotope-labeling experiments, trapping experiments, and EPR experiments.

  DOI：

  10.1021/acs.orglett.5b03124
• 作为产物：
  描述：

  对甲基苯甲醛 在 甲醇 、 sodium tetrahydroborate 、 三氟甲磺酸钠 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 5.0h， 生成 (E)-N-(1,3-di-p-tolylallyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  使用磺酰胺，酰胺和苯胺在烯丙醇中H- * BEA沸石催化的亲核取代

  摘要：

  为了将烯丙醇有效地转化为增值化合物：开发了沸石催化用亲核试剂取代烯丙醇中羟基的第一个实例。在相对温和的反应条件下，沸石催化的取代反应广泛适用于底物。

  DOI：

  10.1002/ejoc.202000296

文献信息

• Electro-oxidative Intermolecular Allylic C(sp³)–H Aminations
  作者：Yulei Wang、Zhipeng Lin、João C. A. Oliveira、Lutz Ackermann

  DOI：10.1021/acs.joc.1c00682

  日期：2021.11.19

  The oxidative intermolecular nitrogenation of C(sp3)–H bonds represents one of the most straightforward strategies to construct nitrogen-containing molecules. However, a sacrificial chemical oxidant is generally required. Herein, we describe electrochemical oxidative intermolecular allylic C(sp3)–H aminations in an undivided cell by electric current. The cross-dehydrogenative amination proceeded efficiently

  C(sp 3 )-H 键的氧化分子间氮化代表了构建含氮分子的最直接的策略之一。然而，通常需要牺牲化学氧化剂。在此，我们通过电流描述了未分割电池中的电化学氧化分子间烯丙基 C(sp 3 )-H 胺化。在无金属和无化学氧化剂的反应条件下，交叉脱氢胺化反应在大范围内有效进行，得到分子 H 2作为唯一的副产物。
• Iridium(III)-Catalyzed Intermolecular Allylic C–H Amidation of Internal Alkenes with Sulfonamides
  作者：Pinki Sihag、Masilamani Jeganmohan

  DOI：10.1021/acs.joc.9b02047

  日期：2019.10.18

  aryl-alkyl alkenes, the amidation selectively takes place at the alkyl-substituted allylic carbon. Meanwhile, the better selectivity was also observed in the unsymmetrical aryl-aryl alkenes having an electron-withdrawing substituent at one of the aryl groups. A possible reaction mechanism involving a π-allyl iridium intermediate was proposed and supported by the deuterium labeling studies. The deuterium labeling

  证明了具有取代基的内酰胺与取代的磺酰胺的Ir（III）催化的直接烯丙基CH酰胺化反应，而没有取代基。本方案以高度原子经济和分步经济的方式提供了取代的烯丙基胺。该反应与对称和不对称内部烯烃以及取代的磺酰胺相容。有趣的是，在芳基-烷基烯烃的反应中，酰胺化选择性地发生在烷基取代的烯丙基碳上。同时，在其中一个芳基上具有吸电子取代基的不对称芳基-芳基烯烃中也观察到更好的选择性。提出了一种可能的涉及π-烯丙基铱中间体的反应机理，并得到了氘标记研究的支持。
• Iron oxide-silver magnetic nanoparticles as simple heterogeneous catalysts for the direct inter/intramolecular nucleophilic substitution of π-activated alcohols with electron-deficient amines
  作者：Xingzhu Xu、Haibo Wu、Zhengyi Li、Xiaoqiang Sun、Zhiming Wang

  DOI：10.1016/j.tet.2015.06.028

  日期：2015.8

  The development of bimetallic iron oxide-silver magnetic nanoparticles (Fe2O3-Ag MNPs) catalytic system provides an efficient heterogeneous synthetic pathway to allylic amines and 1,2-dihydroquinolines involving the direct inter/intramolecular nucleophilic substitution of pi-activated alcohols with electron-deficient amines. The major advantages of the present method are wide substrate scope, simple product separation, low catalyst loading, and magnetically recyclable catalyst. (C) 2015 Elsevier Ltd. All rights reserved.
• Iodine-catalyzed allylic alkylation of sulfonamides and carbamates with allylic alcohols at room temperature
  作者：Wenhan Wu、Weidong Rao、Ya Qin Er、Joanna Kejun Loh、Chai Yun Poh、Philip Wai Hong Chan

  DOI：10.1016/j.tetlet.2008.02.079

  日期：2008.4

  A highly efficient iodine-catalyzed allylic alkylation of a wide variety of sulfonamides and carbamates with allylic alcohols is reported herein. The reaction is operationally straightforward and proceeds under very mild conditions at room temperature in good to excellent yields (up to 99%). (C) 2008 Elsevier Ltd. All rights reserved.
• Transition-Metal-Free Self-Hydrogen-Transferring Allylic Isomerization
  作者：Hong-Xing Zheng、Zu-Feng Xiao、Chuan-Zhi Yao、Qiang-Qiang Li、Xiao-Shan Ning、Yan-Biao Kang、Yong Tang

  DOI：10.1021/acs.orglett.5b03124

  日期：2015.12.18

  Phenanthroline and tert-butoxide have been established as powerful radical initiators in reactions such as the S(RN)1-type coupling reactions due to the cooperation of large heteroarenes and a special feature of tert-butoxide. The first phenanthroline-tert-butoxide-catalyzed transition-metal-free allylic isomerization is described. The resulting ketones are key intermediates for indenes. The control experiments rule out the base-promoted allylic anion pathway. The radical pathway is supported by experimental evidence that includes kinetic study, kinetic isotope effect, isotope-labeling experiments, trapping experiments, and EPR experiments.