1-(4-nitrophenylsulfonyl)-2-p-tolylaziridine | 175222-84-1

• 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-p-tolylaziridine
• 英文别名: 2-(4-Methylphenyl)-1-(4-nitrobenzene-1-sulfonyl)aziridine；2-(4-methylphenyl)-1-(4-nitrophenyl)sulfonylaziridine
• CAS: 175222-84-1
• 化学式: C₁₅H₁₄N₂O₄S
• 分子量: 318.353
• InChiKey: DCFGIZZBKRBQFZ-UHFFFAOYSA-N

物化性质

• 沸点：
  507.5±60.0 °C(Predicted)
• 密度：
  1.422±0.06 g/cm3(Predicted)

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：

  1,3,5-三甲氧基苯 、 1-(4-nitrophenylsulfonyl)-2-p-tolylaziridine 在 zinc trifluoromethanesulfonate 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.75h， 以88%的产率得到4-nitro-N-(2-p-tolyl-2-(2,4,6-trimethoxyphenyl)ethyl)benzenesulfonamide
  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：

  p-nitrobenzenesulfonyl azide 、 Alpha-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-p-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

• Imido Transfer from Bis(imido)ruthenium(VI) Porphyrins to Hydrocarbons:  Effect of Imido Substituents, C−H Bond Dissociation Energies, and Ru^VI/V Reduction Potentials
  作者：Sarana Ka-Yan Leung、Wai-Man Tsui、Jie-Sheng Huang、Chi-Ming Che、Jiang-Lin Liang、Nianyong Zhu

  DOI：10.1021/ja0542789

  日期：2005.11.30

  (BDE) of the hydrocarbons. A linear correlation was observed between log k' (k' is the k2 value divided by the number of reactive hydrogens) and BDE and between log k2 and E(1/2)(Ru(VI/V)); the linearity in the former case supports a H-atom abstraction mechanism. The amidation by [Ru(VI)(TMP)(NNs)2] reverses the thermodynamic reactivity order cumene > ethylbenzene/toluene, with k'(tertiary C-H)/k'(secondary

  [Ru(VI)(TMP)(NSO2R)2]（SO2R = Ms、Ts、Bs、Cs、Ns；R = p-C6H4OMe、p-C6H4Me、C6H5、p-C6H4Cl、p-C6H4NO2）和[ Ru(VI)(Por)(NTs)2] (Por = 2,6-Cl2TPP, F20-TPP) 是通过 [Ru(II)(Por)(CO)] 与 PhI=NSO2R 在 CH2Cl2 中的反应制备的。这些配合物表现出可逆的 Ru(VI/V) 对，E(1/2) = -0.41 到 -0.12 V vs Cp2Fe(+/0)，并与苯乙烯、降冰片烯、顺式环辛烯、茚、乙苯进行酰亚胺转移反应，枯烯、9,10-二氢蒽、呫吨、环己烯、甲苯和四氢呋喃以高达 85% 的产率提供氮丙啶或酰胺。298 K 氮丙啶化/酰胺化反应的二级速率常数 (k2) 确定为 (2.6 +/- 0.1) x 10(-5) 至 14.4 +/- 0.6
• A method for rhodium(II)-catalyzed aziridination of olefins
  作者：Paul Müller、Corine Baud、Yvan Jacquier

  DOI：10.1016/0040-4020(95)00999-x

  日期：1996.1

  decomposition of (N-(p-nitrobenzenesulfonyl)imino)phenyliodinane (PhINNs) in the presence of olefins affords aziridines in yields of 18–85%. The aziridination of cis-β- methylstyrene (1h) and cis-hex-2-ene (1k) is stereospecific. However, with cis-stilbene (1m) a ca. 3:1 mixture of cis- and trans aziridines 2m and 21 is obtained. With chiral catalysts asymmetric inductions in up to 73% ee are obtained

  [Rh 2（OAc）4 ]在烯烃存在下催化分解（N-（对硝基苯磺酰基）亚氨基）苯基碘丁烷（PhINNs），得到的氮丙啶为18-85％。的氮杂环丙烷顺式-β-甲基苯乙烯（1H）和顺式-己-2-烯（1K）是立体有择的。但是，使用顺二苯乙烯（1m）时，获得顺式和反式氮丙啶2m和21的3∶1混合物。使用手性催化剂，可获得高达73％ee的不对称诱导。
• Rhodium perfluorobutyramide (Rh2(pfm)4): a synthetically useful catalyst for olefin aziridinations
  作者：Gregg F. Keaney、John L. Wood

  DOI：10.1016/j.tetlet.2005.04.027

  日期：2005.6

  Rhodium perfluorobutyramide (Rh2(pfm)4) has been shown to catalyze the conversion of olefins to trichloroethoxysulfonyl, nosyl, and tosyl aziridines. Advantages of this aziridination procedure include the microwave-assisted preparation of the catalyst and the practical use of the alkene substrate as the limiting reagent.

  已显示全氟丁酰胺铑（Rh 2（pfm）4）催化烯烃转化为三氯乙氧基磺酰基，壬基和甲苯磺酰基氮丙啶。该叠氮化过程的优点包括催化剂的微波辅助制备和烯烃底物作为限制试剂的实际应用。
• 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。
• 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。