1-(4-nitrophenyl)-N-(trimethylsilyl)methanimine | 160313-81-5

• 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-nitrophenyl)-N-(trimethylsilyl)methanimine
• 英文别名: [1-(4-Nitro-phenyl)-meth-(E)-ylidene]-trimethylsilanyl-amine；1-(4-Nitrophenyl)-N-(trimethylsilyl)methanimine；1-(4-nitrophenyl)-N-trimethylsilylmethanimine
• CAS: 160313-81-5
• 化学式: C₁₀H₁₄N₂O₂Si
• 分子量: 222.319
• InChiKey: MWXMLWUJRDNFDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-nitrophenyl)-N-(trimethylsilyl)methanimine 在 三乙胺 作用下， 以 正己烷 、 正庚烷 、 甲苯 为溶剂， 生成 (+/-)-3-chloro-4-p-nitro-phenyl-azetidin-2-one
  参考文献：
  名称：

  A Trans-Stereoselective Synthesis of 3-Halo-4-alkyl(aryl)-NH-azetidin-2-ones

  摘要：

  Conrotatory ring closure of 1-halo-3-aza-4-alkyl-1,3-dienes in refluxing toluene gives rise to 3-halo-4-aryl-2-azetidinones in satisfactory yields. Dehalogenation of the resulting beta-lactams by tris(trimethylsilyl)silane furnished 3-unsubstituted azetidinones, valuable intermediates in the synthesis of biologically active compounds.

  DOI：

  10.1021/ol005633x
• 作为产物：
  描述：

  对硝基苯甲醛 、 lithium hexamethyldisilazane 在 lithium perchlorate 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 1-(4-nitrophenyl)-N-(trimethylsilyl)methanimine
  参考文献：
  名称：

  高氯酸锂介导的三组分反应制备伯胺

  摘要：

  在乙醚中的高氯酸锂存在下，LPDE、醛、六甲基二硅氮烷钠或六甲基二硅氮烷锂、LHMDS 和不同亲核试剂之间的三组分反应顺利进行，以良好的收率得到伯胺。

  DOI：

  10.1039/a808424f

文献信息

• Organocatalytic Aziridine Synthesis Using F⁺ Salts
  作者：Sean P. Bew、Shirley A. Fairhurst、David L. Hughes、Laurent Legentil、John Liddle、Paolo Pesce、Sanket Nigudkar、Martin A. Wilson

  DOI：10.1021/ol901784m

  日期：2009.10.15

  This paper describes a unique application of the fluoronium cation (F+) as an organocatalyst for mediating the reaction between N-substituted imines and ethyl diazoacetate affording excellent yields of N-substituted aziridines.

  本文介绍了氟阳离子（F +）作为有机催化剂在N-取代的亚胺与重氮乙酸乙酯之间的介导的独特应用，提供了N-取代的氮丙啶的优异收率。
• Lithium Perchlorate Mediated Three Component Reaction for the Preparation of Primary Amines
  作者：Mohammad R. Saidi、Shahrzad Javanshir、Mohammad M. Mojtahedi

  DOI：10.1039/a808424f

  日期：——

  In the presence of lithium perchlorate in diethyl ether, LPDE, a three-component reaction between aldehydes, sodium hexamethyldisilazane or lithium hexamethyldisilazane, LHMDS, and different nucleophiles proceeds smoothly to afford primary amines in good yields.

  在乙醚中的高氯酸锂存在下，LPDE、醛、六甲基二硅氮烷钠或六甲基二硅氮烷锂、LHMDS 和不同亲核试剂之间的三组分反应顺利进行，以良好的收率得到伯胺。
• NOVEL PATHWAY FOR THE SYNTHESIS OF DIAZIRINES, THAT MAY OR MAY NOT BE ENRICHED IN NITROGEN-15
  申请人：UNIVERSITE DE ROUEN NORMANDIE

  公开号：US20220098155A1

  公开（公告）日：2022-03-31

  The present invention concerns a novel method for synthesising diazirines, that may or may not be enriched in nitro-gen-15, from amino acids or imines, via a one-pot synthesis method, comprising the reaction of the starting amino acid or imine with ammonia, which may or may not be enriched in nitrogen-15, and a hypervalent iodine oxidant. The present invention also relates to a method for synthesising ammonia enriched in nitrogen-15. The invention also concerns certain diazirines of formula (I) likely to be obtained by the claimed synthesis method, and also refers to the 15 N 2 -diazirines of formula (I′). The claimed diazirines can be used in photoaffinity labelling. The 15 N 2 -diazirines can also be used in hyperpolarisation, in particular in the medical imaging field.

  本发明涉及一种新型的合成重氮环化合物的方法，可以从氨基酸或亚胺中合成，可能富集于氮-15，采用一锅法合成方法，包括将起始氨基酸或亚胺与氨反应，可能富集于氮-15，并与高价碘氧化剂反应。本发明还涉及一种合成富集于氮-15的氨的方法。本发明还涉及某些可能通过所述合成方法获得的公式（I）的重氮环化合物，并且还涉及公式（I'）的15N2-重氮环化合物。所述的重氮环化合物可用于光亲和标记。15N2-重氮环化合物也可用于超极化，特别是在医学成像领域。
• A Trans-Stereoselective Synthesis of 3-Halo-4-alkyl(aryl)-NH-azetidin-2-ones
  作者：Elisa Bandini、Gianfranco Favi、Giorgio Martelli、Mauro Panunzio、Giovanni Piersanti

  DOI：10.1021/ol005633x

  日期：2000.4.1

  Conrotatory ring closure of 1-halo-3-aza-4-alkyl-1,3-dienes in refluxing toluene gives rise to 3-halo-4-aryl-2-azetidinones in satisfactory yields. Dehalogenation of the resulting beta-lactams by tris(trimethylsilyl)silane furnished 3-unsubstituted azetidinones, valuable intermediates in the synthesis of biologically active compounds.
• Palladium‐Catalyzed Cascade Heck Coupling and Allylboration of Iododiboron Compounds via Diboryl Radicals
  作者：Yi Wei、Xiao‐Yu Xie、Jiabin Liu、Xiaoxiao Liu、Bo Zhang、Xin‐Yi Chen、Shi‐Jun Li、Yu Lan、Kai Hong

  DOI：10.1002/anie.202401050

  日期：2024.4.24

  Geminal bis(boronates) are versatile synthetic building blocks in organic chemistry. The fact that they predominantly serve as nucleophiles in the previous reports, however, has restrained their synthetic potential. Herein we disclose the ambiphilic reactivity of α‐halogenated geminal bis(boronates), of which the first catalytic utilization was accomplished by merging a formal Heck cross‐coupling with a highly diastereoselective allylboration of aldehydes or imines, providing a new avenue for rapid assembly of polyfunctionalized boron‐containing compounds. We demonstrated that this cascade reaction is highly efficient and compatible with various functional groups, and a wide range of heterocycles. In contrast to a classical Pd(0/II) scenario, mechanistic experiments and DFT calculations have provided strong evidence for a catalytic cycle involving Pd(I)/diboryl carbon radical intermediates.