2-(4-bromophenyl)-1-((4-nitrophenyl)sulfonyl)aziridine

• 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-(4-bromophenyl)-1-((4-nitrophenyl)sulfonyl)aziridine
• 英文别名: (N-4-nitrophenylsulfonyl)-2-(4-bromophenyl)aziridine；2-(4-bromophenyl)-1-(4-nitrophenylsulfonyl)aziridine；2-(4-Bromophenyl)-1-(4-nitrophenyl)sulfonylaziridine
• 化学式: C₁₄H₁₁BrN₂O₄S
• 分子量: 383.222
• InChiKey: FQXSESXYUAYDQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  1,3,5-三甲氧基苯 、 2-(4-bromophenyl)-1-((4-nitrophenyl)sulfonyl)aziridine 在 zinc trifluoromethanesulfonate 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以92%的产率得到N-(2-(4-bromophenyl)-2-(2,4,6-trimethoxyphenyl)ethyl)-4-nitrobenzenesulfonamide
  参考文献：
  名称：

  Lewis Acid Catalyzed S_N2-Type Ring Opening of N-Activated Aziridines with Electron-Rich Arenes/Heteroarenes

  摘要：

  An efficient Lewis acid catalyzed S(N)2-type ring opening of substituted aziridines with electron-rich arenes/heteroarenes to provide substituted 2,2-diaryl/heteroarylethylamines in excellent yields and stereoselectivity (er, dr >99:1) is described.

  DOI：

  10.1021/jo401028j
• 作为产物：
  描述：

  4-硝基苯磺酰胺 在 C₄₂H₇₄FeN₆Si₂⁽²⁺⁾*2ClO₄^(1-) 、 potassium hydroxide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 5.5h， 生成 2-(4-bromophenyl)-1-((4-nitrophenyl)sulfonyl)aziridine
  参考文献：
  名称：

  铁（MCP）配合物以烯烃作为限制试剂催化叠氮化

  摘要：

  本文描述了由铁N，N'-二甲基-N，N'-双（2-吡啶基甲基）环己烷-1,2-二胺-（MCP-）和2-（{{ -[[（吡啶-2-基甲基）吡咯烷-2-基]吡咯烷-1-基}甲基）吡啶型（PDP-型）复合物。这些催化剂基于烯烃底物的有限量，在温和条件下影响苯乙烯的叠氮化。

  DOI：

  10.1021/acs.joc.8b00402

文献信息

• Iron(MCP) Complexes Catalyze Aziridination with Olefins As Limiting Reagents
  作者：Mina F. Shehata、Suraj K. Ayer、Jennifer L. Roizen

  DOI：10.1021/acs.joc.8b00402

  日期：2018.5.4

  N′-dimethyl-N,N′-bis(2-pyridinylmethyl)cyclohexane-1,2-diamine- (MCP-) and 2-(1-[(pyridin-2-ylmethyl)pyrrolidin-2-yl]pyrrolidin-1-yl}methyl)pyridine-type (PDP-type) complexes. These catalysts affect styrene aziridination under mild conditions based on a limiting quantity of olefin substrate.

  本文描述了由铁N，N'-二甲基-N，N'-双（2-吡啶基甲基）环己烷-1,2-二胺-（MCP-）和2-（ -[[（吡啶-2-基甲基）吡咯烷-2-基]吡咯烷-1-基}甲基）吡啶型（PDP-型）复合物。这些催化剂基于烯烃底物的有限量，在温和条件下影响苯乙烯的叠氮化。
• Enantioselective Synthesis of 4,5-Dihydropyrroles via Domino Ring-Opening Cyclization (DROC) of<i>N</i>-Activated Aziridines with Malononitrile
  作者：Manas K. Ghorai、Deo Prakash Tiwari

  DOI：10.1021/jo302815m

  日期：2013.3.15

  An efficient and practical strategy for the synthesis of highly functionalized racemic and non-racemic 4,5-dihydropyrroles via domino ring-opening cyclization (DROC) of activated aziridines with malononitrile in excellent yield and stereoselectivity is described. The reaction serves as a tool for the synthesis of a large variety of substituted 4,5-dihydropyrroles in enantiomerically pure forms.

  描述了一种通过活化的氮丙啶与丙二腈的多米诺开环环化（DROC），以优异的收率和立体选择性合成高度官能化的外消旋和非外消旋4,5-二氢吡咯的有效而实用的策略。该反应用作合成对映体纯形式的多种取代的4，5-二氢吡咯的工具。
• A Highly Effective Cobalt Catalyst for Olefin Aziridination with Azides: Hydrogen Bonding Guided Catalyst Design
  作者：Joshua V. Ruppel、Jess E. Jones、Chelsea A. Huff、Rajesh M. Kamble、Ying Chen、X. Peter Zhang

  DOI：10.1021/ol800588p

  日期：2008.5.1

  [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.
• The rhodium(II)-catalyzed aziridination of olefins with {[(4-nitrophenyl)sulfonyl]imino}phenyl-lambda&lt;sup&gt;3&lt;/sup&gt;-iodane
  作者：Paul Müller、Corine Baud、Yvan Jacquier

  DOI：10.1139/cjc-76-6-738

  日期：——

  The aziridination of olefins with (4-nitrophenylsulfonyl)imino)phenyl-lambda(3)-iodane, NsN=IPh (1c), in the presence of [Rh-2(OAc)(4)] proceeds in yields of up to 85% when the olefin is used in large excess. Under optimized conditions, styrene (4a) is aziridinated with 1 equiv. of NsN=IPh (1c) in 64% yield with 2 mol% of catalyst. The aziridines derived from electron-rich olefins undergo ring-opening under the conditions of the aziridination and afford rearrangement products or pyrrolidines. The aziridination is sterospecific with 1,2-dialkyl- and 1,2-arylalkyl-disubstituted olefins, but nonstereospecific with stilbene. The rho-value for aziridination of substituted styrenes is -0.61. No ring-opened products are observed upon aziridination of vinylcyclopropanes. Tn the presence of chiral Rh-II catalysts, the aziridination is enantioselective, affording an ee of 73% with cis-beta-methylstyrene (4k) and Pirrungs [Rh-2(R)-(-)-bnp}(4)] catalyst. The experimental results are consistent with a one-step mechanism for transfer of the nitrenoid moiety from the catalyst to the olefin.
• Guo, Hongchao; Xu, Qihai; Kwon, Ohyun, Journal of the American Chemical Society, 2009, vol. 131, p. 6318 - 6319
  作者：Guo, Hongchao、Xu, Qihai、Kwon, Ohyun

  DOI：——

  日期：——