N-(trifluoromethylsulfonyl)-N-phenylaminobut-3-ene | 667466-00-4

• 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-(trifluoromethylsulfonyl)-N-phenylaminobut-3-ene
• 英文别名: N-but-3-enyl-N-phenyl-trifluoromethanesulfonamide；N-but-3-enyl-1,1,1-trifluoro-N-phenylmethanesulfonamide
• CAS: 667466-00-4
• 化学式: C₁₁H₁₂F₃NO₂S
• 分子量: 279.283
• InChiKey: DFYPPUYEUDEVDB-UHFFFAOYSA-N

物化性质

• 沸点：
  292.8±50.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(trifluoromethylsulfonyl)-N-phenylaminobut-3-ene 在 gold(III) chloride 、 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以55%的产率得到N-(trifluoromethylsulfonyl)-4-methyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Gold-catalyzed intramolecular hydroarylation of olefins. Scope evaluation and preliminary mechanistic studies

  摘要：

  We report a gold-catalyzed intramolecular hydroarylation of unactivated olefins using a combination of AuCl(3)/AgOTf as the catalytic system affording dihydrobenzopyrans, tetralins and tetrahydroquinolines in good yields. For our preliminary mechanistic studies, we have investigated the kinetic isotope effects with deuterated arene compounds and found that this catalytic hydroarylation is consistent with an electrophilic aromatic substitution process. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.122
• 作为产物：
  描述：

  三氟甲磺酸酐 、 N-(3-butenyl)aniline 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到N-(trifluoromethylsulfonyl)-N-phenylaminobut-3-ene
  参考文献：
  名称：

  Ru(III)-Catalyzed Cyclization of Arene-Alkene Substrates via Intramolecular Electrophilic Hydroarylation

  摘要：

  We herein report that RuCl3/AgOTf has proven to be a hydroarylation catalyst with an efficiency and scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-ene substrates of diverse structural features, providing good to excellent yields of cyclization products (chromanes, tetralins, terpenoids, dihydrocoumarins).

  DOI：

  10.1021/ol036385i

文献信息

• Synthesis of tetralin and chromane derivatives via In-catalyzed intramolecular hydroarylation
  作者：Kai Xie、Sizhuo Wang、Ping Li、Xiujian Li、Zhiyong Yang、Xiangyu An、Can-Cheng Guo、Ze Tan

  DOI：10.1016/j.tetlet.2010.06.091

  日期：2010.8

  IN(OTf)(3) was found to be an effective catalyst for the cyclization of omega-aryl-1-alkenes to form tetralin and chromane derivatives Compared with the known Ru-catalyzed version, the In-catalyzed intramolecular cyclization was found to give higher yields and cleaner reactions in some cases The use of cheaper indium salts instead of the expensive noble metal Ru can be advantageous when the reaction is run on a large scale (C) 2010 Elsevier Ltd All rights reserved
• Gold-catalyzed intramolecular hydroarylation of olefins. Scope evaluation and preliminary mechanistic studies
  作者：Mickael Jean、Pierre van de Weghe

  DOI：10.1016/j.tetlet.2011.04.122

  日期：2011.7

  We report a gold-catalyzed intramolecular hydroarylation of unactivated olefins using a combination of AuCl(3)/AgOTf as the catalytic system affording dihydrobenzopyrans, tetralins and tetrahydroquinolines in good yields. For our preliminary mechanistic studies, we have investigated the kinetic isotope effects with deuterated arene compounds and found that this catalytic hydroarylation is consistent with an electrophilic aromatic substitution process. (C) 2011 Elsevier Ltd. All rights reserved.
• Ru(III)-Catalyzed Cyclization of Arene-Alkene Substrates via Intramolecular Electrophilic Hydroarylation
  作者：So Won Youn、Stefan J. Pastine、Dalibor Sames

  DOI：10.1021/ol036385i

  日期：2004.2.1

  We herein report that RuCl3/AgOTf has proven to be a hydroarylation catalyst with an efficiency and scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-ene substrates of diverse structural features, providing good to excellent yields of cyclization products (chromanes, tetralins, terpenoids, dihydrocoumarins).