4-(4-bromophenyl)-2-methyl-1-(toluene-4-sulfonyl)-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: 4-(4-bromophenyl)-2-methyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-imidazole
• 英文别名: 4-(4-bromophenyl)-4,5-dihydro-2-methyl-1-tosyl-1H-imidazole；4-(4-bromophenyl)-2-methyl-1-tosyl-4,5-dihydro-1H-imidazole；2-methyl-4-(4-bromophenyl)-1-tosyl-4,5-dihydro-1H-imidazole；4-(4-Bromophenyl)-2-methyl-1-(4-methylphenyl)sulfonyl-4,5-dihydroimidazole
• 化学式: C₁₇H₁₇BrN₂O₂S
• 分子量: 393.304
• InChiKey: LDOAUEGOLGAAQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 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-(4-bromophenyl)-1-tosylaziridine 、 乙腈 在 bismuth(lll) trifluoromethanesulfonate 作用下， 反应 4.0h， 以99%的产率得到4-(4-bromophenyl)-2-methyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-imidazole
  参考文献：
  名称：

  Bi(OTf)3-促进的 [3+2] N-甲苯磺酰氮丙啶环加成生成咪唑啉的一种新的有效方法

  摘要：

  [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。

  DOI：

  10.1002/ejoc.201100270

文献信息

• A Metal-Free Protocol for Aminofunctionalization of Olefins Using TsNBr₂
  作者：Kamal Krishna Rajbongshi、Indranirekha Saikia、Loukrakpam Dineshwori Chanu、Subhasish Roy、Prodeep Phukan

  DOI：10.1021/acs.joc.6b00785

  日期：2016.7.1

  proceeds rapidly under mild conditions with high regioselectivity. Olefins react with TsNBr2 in moist THF to form δ-amino ether at room temperature. Treatment of TsNBr2 with olefin in MeCN at room temperature produced imidazoline in high yield. Further modification of the reaction condition resulted in the development of a one-step procedure for the synthesis of N-acetyl,N′-tosyl diamine derivatives directly

  已经发现N，N-二溴-对甲苯磺酰胺（TsNBr 2）是用于各种氨基官能化反应的有效试剂。该试剂既可作为亲电子溴源，也可作为胺在不同条件下与烯烃反应，从而产生氨基醚，咪唑啉，二胺和氨基溴。该反应在温和条件下以高区域选择性快速进行。烯烃与TsNBr 2在潮湿的THF中反应，在室温下形成δ-氨基醚。在室温下，在MeCN中用烯烃处理TsNBr 2可以高产率生产咪唑啉。反应条件的进一步改变导致了一步合成步骤的发展。N-乙酰基，N'-甲苯磺酰基二胺衍生物直接来自烯烃。当烯烃与2.4摩尔当量TsNBr的处理2中K的存在2 CO 3，Ñ，Ñ在适中的产率获得'-ditosyl二胺衍生物。当在室温下在干燥的CH 2 Cl 2中用试剂处理烯烃时，观察到氨基溴的瞬时形成。
• 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。
• Photoredox-Induced Functionalization of Alkenes for the Synthesis of Substituted Imidazolines and Oxazolidines
  作者：Jian-Qiang Chen、Wan-Lei Yu、Yun-Long Wei、Teng-Hui Li、Peng-Fei Xu

  DOI：10.1021/acs.joc.6b02377

  日期：2017.1.6

  A one-pot, three-component cascade reaction combining photoredox catalyzed radical addition and formal [3 + 2] annulation was developed. With this approach, highly concise syntheses of imidazoline and oxazolidine derivatives have been achieved. The advantages of this transformation are good to excellent yields, mild reaction conditions, operational simplicity, and easy accessibility of raw materials

  结合光氧化还原催化的自由基加成和正式的[3 + 2]环化反应的一锅三组分级联反应得到了发展。通过这种方法，已实现了咪唑啉和恶唑烷衍生物的高度简洁的合成。这种转化的优点是具有优异的收率，温和的反应条件，操作简单和易于获得原料的优点。
• 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.