4-methyl-N-(2-phenyl-2-(furan-2-yl)ethyl)benzenesulfonamide

• 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-(2-phenyl-2-(furan-2-yl)ethyl)benzenesulfonamide
• 英文别名: N-(2-(furan-2-yl)-2-phenylethyl)-4-methylbenzenesulfonamide；4-methyl-N-(2-phenyl-2-furan-2-ylethyl)benzenesulfonamide；N-[2-(furan-2-yl)-2-phenylethyl]-4-methylbenzenesulfonamide
• 化学式: C₁₉H₁₉NO₃S
• 分子量: 341.431
• InChiKey: JIUPROPMWUWMOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  67.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  呋喃 、 2-苯基-1-甲苯磺酰啶 在 gold(III) chloride 、 silver trifluoromethanesulfonate 作用下， 以 硝基甲烷 为溶剂， 反应 0.03h， 以64%的产率得到4-methyl-N-(2-phenyl-2-(furan-2-yl)ethyl)benzenesulfonamide
  参考文献：
  名称：

  氯化金/三氟甲磺酸银：氮丙啶与电子富集的芳烃开环反应的高效催化剂

  摘要：

  发现氯化金（III）/三氟甲磺酸银是在氮丙啶与富电子芳烃的开环中作为高效催化剂的催化剂，在温和的反应条件下，以良好或极好的收率提供了所需的β-芳基胺。

  DOI：

  10.1002/adsc.200700101

文献信息

• Gold(III) Chloride/Silver Triflate: A Highly Efficient Catalyst for Ring-Opening Reaction of Aziridines with Electron-Rich Arenes
  作者：Xiaoyu Sun、Wei Sun、Renhua Fan、Jie Wu

  DOI：10.1002/adsc.200700101

  日期：2007.9.3

  Gold(III) chloride/silver triflate was found to a highly efficient catalyst in the ring-opening of aziridines with electron-rich arenes and the desired β-arylamines were afforded in good to excellent yields under mild reaction conditions.

  发现氯化金（III）/三氟甲磺酸银是在氮丙啶与富电子芳烃的开环中作为高效催化剂的催化剂，在温和的反应条件下，以良好或极好的收率提供了所需的β-芳基胺。
• A facile C-arylation of N-tosyl aziridines via Ag(I) catalysis
  作者：Milan Bera、Sujit Roy

  DOI：10.1016/j.tetlet.2007.07.200

  日期：2007.10

  N-Tosyl aziridines react with a variety of arenes and heteroarenes in the presence of 1-2% of silver hexafluorophosphate at room temperature to afford the corresponding beta-aryl amine derivatives in excellent yields and with high regioselectivity. (c) 2007 Elsevier Ltd. All rights reserved.
• FeCl3: an efficient catalyst for reactions of electron-rich arenes with imines or aziridines
  作者：Zhiyong Wang、Xiaoyu Sun、Jie Wu

  DOI：10.1016/j.tet.2008.03.081

  日期：2008.5

  Iron(III) chloride was discovered highly effective as catalyst in the Friedel-Crafts reactions of electron-rich arenes with imines or aziridines. It was found that reactions of imines were highly substrate-dependent, which generated mono- or double-addition products, while arenes reacted with aziridines regioselectively leading to the formation of desired ring-opening products in 2 min with moderate to good yields. (C) 2008 Elsevier Ltd. All rights reserved.
• InCl3-catalyzed regioselective opening of aziridines with heteroaromatics
  作者：J.S Yadav、B.V.S Reddy、Sunny Abraham、G Sabitha

  DOI：10.1016/s0040-4039(02)00015-1

  日期：2002.2

  A variety of N-tosylaziridines undergo ring opening with pyrrole, furan, thiophene and indole in the presence of a catalytic amount of indium trichloride at ambient temperature to afford the corresponding beta-aminoheterocycles in good yields with high regioselectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Silver(I)−Diene Complexes as Versatile Catalysts for the <i>C</i>-Arylation of <i>N</i>-Tosylaziridines: Mechanistic Insight from In Situ Diagnostics
  作者：Milan Bera、Sujit Roy

  DOI：10.1021/jo100260k

  日期：2010.7.2

  31P, 109Ag) and ESI-MS probe: (I) evaluation of Hammett reaction constant (ρ); (II) correlation of initial rate (k) versus cone angle (θ) of ligand L for reactions mediated by [Ag(COD)2]PF6/L (where L is a phosphine or a phosphite ligand); (III) identification of silver−arene intermediates in solution; and (IV) correlation of initial rate (k) with ΔHOMO−LUMO of [Ag(diene)2]PF6 obtained from preliminary

  银（I）络合物将[Ag（二烯）2 ] + ý - （其中，二烯烃=环辛二烯，降冰片二烯，和1,3-环己二烯; Y - = PF 6 -，BF 4 - ）有效地催化的芳基化Ñ与-tosylaziridines芳烃和杂芳烃在环境条件下可提供相应的具有出色区域选择性的β-芳基胺衍生物。为了了解底物活化的性质以及初始键断裂/制备步骤，借助原位NMR（1 H，31 P，109Ag）和ESI-MS探针：（I）Hammett反应常数（ρ）的评估；（II）由[Ag（COD）2 ] PF 6 / L（其中L是膦或亚磷酸酯配体）介导的反应的配体L的初始速率（k）与锥角（θ）的相关性；（III）鉴定溶液中的银芳烃中间体；（IV）初始速率（k）与从初步DFT研究获得的[Ag（二烯）2 ] PF 6的ΔHOMO-LUMO的相关性。研究I得出ρ值为-0.586，表明亲电干扰的程度比典型的路易斯酸催化过程小得多。研究二