4-甲基-2-硝基-1-[2-(三甲基甲硅烷基)乙炔基]苯 | 106851-21-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-甲基-2-硝基-1-[2-(三甲基甲硅烷基)乙炔基]苯
• 英文名称: trimethyl((4-methyl-2-nitrophenyl)ethynyl)silane
• 英文别名: 1-(4-methyl-2-nitrophenyl)-2-trimethylsilylacetylene；4-methyl-2-nitro-1-[2-(trimethylsilyl)ethynyl]benzene；Trimethyl-[2-(4-methyl-2-nitrophenyl)ethynyl]silane
• CAS: 106851-21-2
• 化学式: C₁₂H₁₅NO₂Si
• 分子量: 233.342
• InChiKey: GYVHXGQCIANAJF-UHFFFAOYSA-N

物化性质

• 熔点：
  55-57 °C
• 沸点：
  298.3±40.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-甲基-2-硝基-1-[2-(三甲基甲硅烷基)乙炔基]苯 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 溶剂黄146 作用下， 以 溶剂黄146 为溶剂， 反应 11.0h， 生成 6-甲基吲哚
  参考文献：
  名称：

  6-substituted indoles from o-halonitrobenzenes

  摘要：

  DOI：

  10.1016/s0040-4039(00)84339-7
• 作为产物：
  描述：

  4-溴-3-硝基甲苯 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 2.0h， 生成 4-甲基-2-硝基-1-[2-(三甲基甲硅烷基)乙炔基]苯
  参考文献：
  名称：

  Gold-Catalyzed Stereoselective Synthesis of Azacyclic Compounds through a Redox/[2 + 2 + 1] Cycloaddition Cascade of Nitroalkyne Substrates

  摘要：

  We report a new redox/cycloaddition cascade on readily available 1-alkynyl-2-nitrobenzenes that produces complex azacyclic compounds stereoselectively. The core structures of the resulting products are constructed through a formal [2 + 2 + 1] cycloaddition among a-carbonyl carbenoids, nitroso species, and external alkenes.

  DOI：

  10.1021/ja110514s

文献信息

• Synthesis of Piperidinone and Azepanone Fused Indoles via a Wagner–Meerwein Type 1,2-Amide Migration of 2-Spiropseudoindoxyls
  作者：Guido Verniest、Niels Marien、Ting Luo

  DOI：10.1055/s-0036-1588138

  日期：——

  Spiropseudoindoxyls were synthesized by using a gold(III)-catalyzed intramolecular nitroalkyne redox–dipolar cycloaddition cascade. These compounds were then transformed into novel piperidinone and azepanone fused indoles via a straightforward hydrogenation. The reaction mechanism of this ring expansion is believed to proceed through a rare Wagner–Meerwein type 1,2-amide migration.

  Spiropseudoindoxyls 是通过使用金 (III) 催化的分子内硝基炔氧化还原 - 偶极环加成级联反应合成的。然后通过直接的氢化将这些化合物转化为新型哌啶酮和氮杂环庚酮稠合吲哚。这种扩环的反应机制被认为是通过罕见的 Wagner-Meerwein 型 1,2-酰胺迁移进行的。
• A palladium-catalyzed synthesis of isatins (1H-Indole-2,3-diones) from 1-(2-haloethynyl)-2-nitrobenzenes
  作者：Björn C.G. Söderberg、Sobha P. Gorugantula、Chet R. Howerton、Jeffrey L. Petersen、Shubhada W. Dantale

  DOI：10.1016/j.tet.2009.06.098

  日期：2009.9

  An inherently regiospecific synthesis of isatins (1H-indole-2,3-diones) starting from 1-halo-2-nitrobenzenes is described. The isatins are formed by an intramolecular palladium-catalyzed annulation of 2-(2-haloethynyl)-1-nitrobenzenes via the formation of 2-haloisatogens.

  描述了从1-卤代-2-硝基苯开始的本质上区域特异性的靛红（1 H-吲哚-2，3-二酮）的区域特异性合成。通过分子内钯催化的2-（2-卤乙炔基）-1-硝基苯环化形成2-卤代致烟碱来形成所述靛红。
• Synthesis of 2-Spiropseudoindoxyls via an Intramolecular Nitroalkyne Redox–Dipolar Cycloaddition Cascade
  作者：Niels Marien、Ben Brigou、Balazs Pinter、Frank De Proft、Guido Verniest

  DOI：10.1021/ol503364w

  日期：2015.1.16

  Novel spiropseudoindoxyls were synthesized in high yields via a fully regioselective Au(III)-catalyzed cycloisomerization of easily obtainable o-nitrophenylpropiolamides, followed by an intramolecular dipolar cycloaddition as key steps. This one-pot cascade reaction resulted in new tetracyclic pseudoindoxyls, which were hydrogenated toward the title compounds as single diastereomers via N-O cleavage. The mechanism of the gold catalyzed cycloisomerization was studied by DFT and suggests a reaction path without the intermediacy of gold carbenoid species in these cases.
• 2-Iodoisatogens: Versatile Intermediates for the Synthesis of Nitrogen Heterocycles
  作者：Elvis J. M. Maduli、Steven J. Edeson、Stephen Swanson、Panayiotis A. Procopiou、Joseph P. A. Harrity

  DOI：10.1021/ol503487f

  日期：2015.1.16

  A Cu-promoted cyclization of 2-nitrophenyl iodoacetylenes provides a direct route to a range of 2-iodoisatogens. These compounds represent useful intermediates for the late-stage elaboration of the C-I bond to furnish isatins and a range of alternative heterocyclic products.
• TISCHLER, A. N.;LANZA, T. J., TETRAHEDRON LETT., 1986, 27, N 15, 1653-1656
  作者：TISCHLER, A. N.、LANZA, T. J.

  DOI：——

  日期：——