1-(4-nitrophenylsulfonyl)-2-m-tolylaziridine

• 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: 1-(4-nitrophenylsulfonyl)-2-m-tolylaziridine
• 英文别名: 2-(3-Methylphenyl)-1-(4-nitrophenyl)sulfonylaziridine
• 化学式: C₁₅H₁₄N₂O₄S
• 分子量: 318.353
• InChiKey: FFOHGUQIVBQEDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-vinylidenesuccinic acid diethyl ester 、 1-(4-nitrophenylsulfonyl)-2-m-tolylaziridine 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 trans-diethyl 2-(4-nitrobenzyl)-5-m-tolyl-1,4,5,6-tetrahydropyridine-3,4-dicarboxylate 、
  参考文献：
  名称：

  Guo, Hongchao; Xu, Qihai; Kwon, Ohyun, Journal of the American Chemical Society, 2009, vol. 131, p. 6318 - 6319

  摘要：

  DOI：
• 作为产物：
  描述：

  p-nitrobenzenesulfonyl azide 、 3-甲基苯乙烯 在 C₇₈H₉₅CoN₈O₄ 作用下， 以 氯苯 为溶剂， 反应 18.0h， 以89%的产率得到1-(4-nitrophenylsulfonyl)-2-m-tolylaziridine
  参考文献：
  名称：

  A Highly Effective Cobalt Catalyst for Olefin Aziridination with Azides: Hydrogen Bonding Guided Catalyst Design

  摘要：

  [Co(P1)], which was designed on the basis of potential hydrogen-bonding interactions in the metal-nitrene intermediate, is a highly active aziridination catalyst with azides. [Co(P1)] can effectively aziridinate various aromatic olefins with arylsulfonyl azides under mild conditions, forming sulfonylated aziridines in excellent yields. The Co-based system enjoys several attributes associated with the relatively low cost of cobalt and the wide accessibility of arylsulfonyl azides. Furthermore, it generates stable dinitrogen as the only byproduct.

  DOI：

  10.1021/ol800588p

文献信息

• Nitrene Transfer Reactions Catalyzed by Gold Complexes
  作者：Zigang Li、Xiangyu Ding、Chuan He

  DOI：10.1021/jo060016t

  日期：2006.8.1

  We report here the first gold-catalyzed nitrene transfer reaction. A gold(I) compound, supported by 4,4‘,4‘ ‘-tri-tert-butyl-2,2‘:6‘,2‘ ‘-terpyridine (tBu3tpy) as the ligand, efficiently catalyzes olefin aziridination with the use of the commercially available oxidant PhI(OAc)2 and sulfonamides. This system also mediates carbene insertion into benzene.

  我们在这里报告了第一个金催化的腈转移反应。由4,4'，4''-三叔丁基-2,2'：6'，2'-叔吡啶（t Bu 3 tpy）担载的金（I）化合物有效催化烯烃使用可商购的氧化剂PhI（OAc）2和磺酰胺进行叠氮化。该系统还介导卡宾插入苯中。
• Phosphine-promoted [4 + 3] annulation of allenoate with aziridines for synthesis of tetrahydroazepines: phosphine-dependent [3 + 3] and [4 + 3] pathways
  作者：Honglei Liu、Yan Lin、Yan Zhao、Miaoren Xiao、Leijie Zhou、Qijun Wang、Cheng Zhang、Dongqi Wang、Ohyun Kwon、Hongchao Guo

  DOI：10.1039/c8ra09852b

  日期：——

  In this manuscript, phosphine-dependent [3 + 3] and [4 + 3] annulation reactions of allenoate with aziridines were disclosed. The alkyldiphenylphosphine-promoted [4 + 3] annulation of allenoate with aziridines has been achieved under mild conditions, providing biologically interesting functionalized tetrahydroazepines in moderate to excellent yield with moderate to excellent regioselectivity and diastereoselectivity

  在这篇手稿中，公开了联烯酸酯与氮丙啶的膦依赖性[3 + 3]和[4 + 3]成环反应。在温和条件下实现了烷基二苯基膦促进的联烯酸酯与氮丙啶的[4 + 3]环化，以中等至优异的产率和中等至优异的区域选择性和非对映选择性提供了具有生物学意义的官能化四氢氮杂庚类化合物。
• Metal Porphyrin Catalyzed Olefin Aziridination with Sulfonyl Azides
  申请人：Zhang X. Peter

  公开号：US20110112288A1

  公开（公告）日：2011-05-12

  Cobalt(II) complex of P1 [Co(P1)], a new porphyrin that was designed on the basis of potential hydrogen bonding interactions in the metal-nitrene intermediate, is a highly active catalyst for olefin aziridination with azides. The [Co(P1)]-based system can be effectively employed for different combinations of aromatic olefins and arysulfonyl azides, synthesizing various sulfonylated aziridines in excellent yields. Besides its mild catalytic conditions, the Co-catalyzed aziridination process enjoys several attributes associated with the relatively low cost of cobalt and widely accessible arylsulfonyl azides. Furthermore, it generates stable dinitrogen as the only by-product.