2-benzyl-4-phenyl-1-tosyl-4,5-dihydro-1H-imidazole

• 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: 2-benzyl-4-phenyl-1-tosyl-4,5-dihydro-1H-imidazole
• 英文别名: 2-Benzyl-1-(4-methylphenyl)sulfonyl-4-phenyl-4,5-dihydroimidazole
• 化学式: C₂₃H₂₂N₂O₂S
• 分子量: 390.506
• InChiKey: ZUPVAJSELGLADJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-苯基-1-甲苯磺酰啶 、 苯乙腈 在 phosphomolybdic acid 、 silica gel 作用下， 反应 2.0h， 以80%的产率得到2-benzyl-4-phenyl-1-tosyl-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  Heteropoly Acid as Efficient, Cost-effective, and Recyclable Solid Acid for the Rapid Synthesis of Substituted Imidazolines

  摘要：

  在温和反应条件下，氮杂环丙烷与一系列腈在10摩尔%二氧化硅负载的磷钼酸（PMA-SiO2）催化下顺利开环，高区域选择性地得到相应的咪唑啉，产率良好。采用二氧化硅作为固体载体，便于催化剂的回收和重复使用，从而使该过程操作简单、更加便捷且经济有效。

  DOI：

  10.1246/cl.2008.824

文献信息

• Studies on the Reaction of Aziridines with Nitriles and Carbonyls:  Synthesis of Imidazolines and Oxazolidines
  作者：Shikha Gandhi、Alakesh Bisai、B. A. Bhanu Prasad、Vinod K. Singh

  DOI：10.1021/jo062564c

  日期：2007.3.1

  presence of molecular sieves. Among various triflates, Zn(OTf)2 has been found to be the best. The cleavage of the N-Ts bond of the cyclized products has been studied in order to make it more versatile in synthesis. The mechanistic aspect of the reaction has been studied by using chiral aziridines as substrates. These formal [3 + 2] cycloaddition reactions of aziridines with nitriles and carbonyls proceed

  在多种路易斯酸的存在下，已经研究了N-甲苯磺酰基氮丙啶与腈和羰基的反应生成咪唑啉和恶唑烷。用1当量的BF 3 ·Et 2 O或Et 3 OBF 4在CH 2 Cl 2中反应是有效的。然而，在无溶剂条件下，金属三氟甲磺酸酯具有催化作用，可为N-甲苯磺酰氮丙啶与腈环加成反应提供最佳结果。在分子筛存在下，与羰基化合物的相同反应在CH 2 Cl 2中进行得最好。在各种三氟甲磺酸酯中，Zn（OTf）2被发现是最好的。为了使其在合成中更具通用性，已经研究了环化产物的N -Ts键的裂解。已经通过使用手性氮丙啶作为底物研究了反应的机理。氮丙啶与腈和羰基的这些正式的[3 + 2]环加成反应以Ritter方式进行。
• Heteropoly Acid as Efficient, Cost-effective, and Recyclable Solid Acid for the Rapid Synthesis of Substituted Imidazolines
  作者：J. S. Yadav、B. V. Subba Reddy、T. Pandurangam、U. V. Subba Reddy

  DOI：10.1246/cl.2008.824

  日期：2008.8.5

  Aziridines undergo smooth ring opening with a range of nitriles in the presence of 10 mol % of phosphomolybdic acid supported on silica gel (PMA–SiO2) under mild reaction conditions to afford the corresponding imidazolines in good yields and with high regioselectivity. The use of silica gel as solid support facilitates an easy recovery and reuse of the catalyst thereby making the process quite simple, more convenient, and cost-effective.

  在温和反应条件下，氮杂环丙烷与一系列腈在10摩尔%二氧化硅负载的磷钼酸（PMA-SiO2）催化下顺利开环，高区域选择性地得到相应的咪唑啉，产率良好。采用二氧化硅作为固体载体，便于催化剂的回收和重复使用，从而使该过程操作简单、更加便捷且经济有效。
• A New and Efficient Procedure for Bi(OTf)3-Promoted [3+2] Cycloaddition of N-Tosylaziridines to Yield Imidazolines
  作者：Xing Li、Xueqi Yang、Honghong Chang、Yanwei Li、Bin Ni、Wenlong Wei

  DOI：10.1002/ejoc.201100270

  日期：2011.6

  [3+2] Cycloaddition of a series of substituted N-tosylaziridines with various nitriles promoted by Bi(OTf)3 is described for the synthesis of substituted imidazolines under mild reaction conditions. The procedure works well over a range of substrates to give the corresponding products in good to excellent yields (up to 99 %).

  [3+2] 一系列取代的 N-甲苯磺酰基氮丙啶与由 Bi(OTf)3 促进的各种腈的环加成反应用于在温和的反应条件下合成取代的咪唑啉。该程序在一系列基材上运行良好，以提供良好到极好的产率（高达 99%）的相应产品。
• Synthesis of substituted imidazolines via [3+2]-cycloaddition of aziridines with nitriles
  作者：B.A.Bhanu Prasad、Ghanshyam Pandey、Vinod K Singh

  DOI：10.1016/j.tetlet.2003.12.015

  日期：2004.2

  An efficient synthesis of 2,4-disubstituted 1H-imidazolines from aziridines and nitriles in the presence of BF3-E(2)tO or triethyloxonium tetrafluoroborate has been described. The reaction proceeds via a [3+2]-cycloaddition reaction. Most of the nitriles successfully underwent cycloaddition reactions with aziridines even at room temperature in a very short time. (C) 2003 Elsevier Ltd. All rights reserved.
• Sc(OTf)3-Catalyzed [3+2]-cycloaddition of aziridines with nitriles under solvent-free conditions
  作者：Jie Wu、Xiaoyu Sun、Hong-Guang Xia

  DOI：10.1016/j.tetlet.2006.01.021

  日期：2006.3

  [3+2]-Cycloaddition of aziridines with various nitriles in the absence of organic solvent catalyzed by Sc(OTf)(3) afforded the corresponding imidazolines in good to excellent yields under extremely mild reaction conditions. (c) 2006 Elsevier Ltd. All rights reserved.