nitro-triphenyl-ethene | 5670-70-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: nitro-triphenyl-ethene
• 英文别名: α-nitro-α'-phenylstilbene；Nitro-triphenyl-aethen；1,1,2-Triphenyl-2-nitro-aethylen；1,1,2-Triphenyl-2-nitroaethylen；1,1,2-Triphenyl-2-nitroethylen；1-Nitro-1,2,2-triphenylethylen；Nitrotriphenylethylene；(2-nitro-1,2-diphenylethenyl)benzene
• CAS: 5670-70-2
• 化学式: C₂₀H₁₅NO₂
• 分子量: 301.345
• InChiKey: QQHBQQBPBGILDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2904209090

反应信息

• 作为反应物：
  描述：

  nitro-triphenyl-ethene 在 亚磷酸三乙酯 作用下， 反应 2.0h， 以100%的产率得到2,3-二苯基吲哚
  参考文献：
  名称：

  Reactions of ethyl phosphites with .beta.-nitrostyrenes. The role of nitrosoalkenes as intermediates

  摘要：

  3-Phenyl-2-substituted-indoles are formed in high yields in the reaction of Ph2C=C(R)NO2 (R = H, Me, Ph) with (EtO)3P at 150-degrees-C while reaction with (EtO)2PO-/(EtO)2P(O)H at room temperature forms the aziridines 1 with R = H, Me, Ph. 2,2-Diphenyl-3-substituted-2H-azirines formed by deoxygenation of the Michael-type adducts are postulated as intermediates. Reactions of PhCH=C(R)NO2 (R = H, Me, Ph) with (EtO)3P at 150-degrees-C or (EtO)2PO-/(EtO)2P(O)H at room temperature give products resulting from the addition of the phosphorus nudeophile at the benzylidene carbon atom. Evidence for the formartion of cyclic structures with pentacoordinated phosphorus atoms is presented for the reaction of Ph2C=C(Me)NO2 with (EtO)2PO-/EtO)2P(O)H and for PhCH=C(R)NO2 (R = H, Me, Ph) with (EtO)3P. The Michael-type adducts PhCH[P(O)(OEt)2]CH(R)NO2 (R = Me, Ph) undergo reaction upon treatment with aqueous base at 80-100-degrees-C followed by acidification to yield the 3-(diethoxyphosphinyl)-2-R-N-hydroxyindoles. 4-(Diethoxyphosphinyl)-3-R-4H-1,2-benzoxazines (13, R = Me, Ph) are formed by reaction with 85% H2SO4 Of the adducts of PhCH=C(R)NO2 with (EtO)2PO (R = Me) or (EtO)3P (R = Ph).

  DOI：

  10.1021/jo00050a026
• 作为产物：
  描述：

  ethyl nitroso(2,2,2-triphenylethyl)carbamate 在 乙醚 、 mixture of gaseous nitrogen oxides 、 sodium ethanolate 、 sodium sulfate 作用下， 生成 nitro-triphenyl-ethene
  参考文献：
  名称：

  Aliphatic Diazo Compounds. The Preparation and Rearrangement of Diazo-β,β,β-triphenylethane¹

  摘要：

  DOI：

  10.1021/ja01304a038

文献信息

• Synthetic Diversity from a Versatile and Radical Nitrating Reagent
  作者：Kun Zhang、Benson Jelier、Alessandro Passera、Gunnar Jeschke、Dmitry Katayev

  DOI：10.1002/chem.201902966

  日期：2019.10.8

  We leverage the slow liberation of nitrogen dioxide from a newly discovered, inexpensive succinimide-derived reagent to allow for the C-H diversification of alkenes and alkynes. Beyond furnishing a library of aryl β-nitroalkenes, this reagent provides unparalleled access to β-nitrohydrins and β-nitroethers. Detailed mechanistic studies strongly suggest that a mesolytic N-N bond fragmentation liberates

  我们利用新发现的廉价琥珀酰亚胺衍生试剂缓慢释放二氧化氮，以实现烯烃和炔烃的CH多样化。除了提供芳基β-硝基烯烃的文库之外，该试剂还提供了无与伦比的访问β-硝基醇和β-硝基醚的途径。详细的机理研究强烈表明，介观的NN键断裂会释放出一个硝基自由基。使用原位光敏电子顺磁共振波谱，我们观察到了硝酮自旋捕集在溶液中的硝酰基自由基的直接证据。为了进一步展示N-硝基琥珀酰亚胺在光氧化还原条件下的多功能性，提出了广泛的CH配体的后期多样化制备异恶唑啉和异恶唑的方法。该方法允许由酮伴侣形成原位腈氧化物，当在不存在双亲亲子的情况下进行时，通过形成相应的呋喃烷来检测其存在。使用腈，环氧乙烷和炔烃或炔烃进行的1,3-偶极环加成反应，是通过使用温和，区域选择性且具有广泛化学选择性的通用方案，在单个操作步骤中进行的。
• Photochemical and Chemical Reduction of Nitroalkenes Using Viologens as an Electron Phase-Transfer Catalyst
  作者：Hideo Tomioka、Koichi Ueda、Hirofumi Ohi、Yasuji Izawa

  DOI：10.1246/cl.1986.1359

  日期：1986.8.5

  An amphiphilic electron acceptor, i.e., N,N′-dioctyl-4,4′-bipyridinium, was used as an electron carrier between water–oil two phases, in which nitroalkenes in organic phase were readily reduced to the corresponding oximes and/or carbonyl compounds.

  一种两亲性电子受体，即 N,N′-二辛基-4,4′-联吡啶鎓，被用作水油两相之间的电子载体，有机相中的硝基烯类很容易被还原成相应的肟和/或羰基化合物。
• Iron(III) nitrate-induced aerobic and catalytic oxidative cleavage of olefins
  作者：Toru Amaya、Hayato Fujimoto

  DOI：10.1016/j.tetlet.2018.05.070

  日期：2018.7

  Microwave-assisted catalytic oxidative cleavage of olefins using Fe(NO3)3·9H2O under O2 is reported. This reaction system is particularly effective when 9-benzylidene-9H-fluorene derivatives are used as substrates even though they are tri- and tetra-substituted olefins.

  报道了在O 2下使用Fe（NO 3）3 ·9H 2 O进行的微波辅助的烯烃催化氧化裂解。当使用9-亚苄基-9 H-芴衍生物作为底物时，即使它们是三和四取代的烯烃，该反应体系也特别有效。
• Phenylations of β-Nitrostyrene Derivatives with Benzene by the Use of Palladium(II) Acetate
  作者：Kimiaki Yamamura、Setsuo Watarai

  DOI：10.1246/bcsj.48.3757

  日期：1975.12

  The phenylations of several β-nitrostyrene derivatives with benzene in the presence of palladium(II) acetate have been studied. The nitro group of the β-nitrostyrenes investigated affects the phenylations very strongly, because of its powerful electron-withdrawing nature, and a high reactivity and regiospecificity were observed.

  研究了几种 β-硝基苯乙烯衍生物在乙酸钯 (II) 存在下与苯的苯化反应。所研究的 β-硝基苯乙烯的硝基由于其强大的吸电子性质而对苯基化产生非常强烈的影响，并且观察到高反应性和区域特异性。
• Buevich,V.A. et al., Journal of Organic Chemistry USSR (English Translation), 1970, vol. 6, p. 661 - 663
  作者：Buevich,V.A. et al.

  DOI：——

  日期：——