(3'-nitrobenzyl)-3-nitrobenzoate | 859146-54-6

• 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: (3'-nitrobenzyl)-3-nitrobenzoate
• 英文别名: 3'-nitrobenzyl 3-nitrobenzoate；3-nitrobenzyl 3-nitrobenzoate；3-nitro-benzoic acid-(3-nitro-benzyl ester)；3-Nitro-benzoesaeure-(3-nitro-benzylester)；3,3'-Dinitrobenzoesaeure-benzylester；(3-Nitrophenyl)methyl 3-nitrobenzoate
• CAS: 859146-54-6
• 化学式: C₁₄H₁₀N₂O₆
• 分子量: 302.243
• InChiKey: GNTJSJYOXWIEMN-UHFFFAOYSA-N

物化性质

• 熔点：
  146-147 °C
• 沸点：
  490.8±25.0 °C(Predicted)
• 密度：
  1.427±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3'-nitrobenzyl)-3-nitrobenzoate 、 氢溴酸 生成 3-硝基溴苄 、 间硝基苯甲酸
  参考文献：
  名称：

  Tischtschenko; Ssum, Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1906, vol. 38, p. 513

  摘要：

  DOI：
• 作为产物：
  描述：

  3-硝基苯甲醇 在 碘 、 potassium carbonate 作用下， 以 叔丁醇 为溶剂， 反应 16.0h， 以95%的产率得到(3'-nitrobenzyl)-3-nitrobenzoate
  参考文献：
  名称：

  使用分子碘将醇轻松氧化为酯

  摘要：

  成功地进行了一种简单，高效且高收率的方法，将醇与分子碘和碳酸钾氧化转化为各种类型的酯和酮。

  DOI：

  10.1016/j.tet.2005.03.097

文献信息

• Thorium complexes possessing expanded ring N-heterocyclic iminato ligands: synthesis and applications
  作者：Tapas Ghatak、Shani Drucker、Natalia Fridman、Moris S. Eisen

  DOI：10.1039/c7dt02126g

  日期：——

  Six and seven membered N-heterocyclic iminato ligands (L) are introduced allowing access a new class of Th(IV) complexes of the type Cp*2Th(L)(CH3). These complexes were studied in the Tishchenko reaction. Stoichiometric reactions together with kinetic and thermodynamic studies permit us to propose a plausible mechanism.

  引入六个和七个成员的N-杂环亚氨基配体（L），从而可以访问类型为Cp * 2 Th（L）（CH 3）的新型Th（IV）配合物。在Tishchenko反应中研究了这些配合物。化学计量反应以及动力学和热力学研究允许我们提出一个合理的机理。
• Synthesis, characterization and catalytic performances of benzimidazolin-2-iminato actinide (IV) complexes in the Tishchenko reactions for symmetrical and unsymmetrical esters
  作者：Heng Liu、Maxim Khononov、Natalia Fridman、Matthias Tamm、Moris S. Eisen

  DOI：10.1016/j.jorganchem.2017.09.020

  日期：2018.2

  benzimdazolin-2-iminato actinide−(IV) complexes [(Bim7-MeDipp/MeN)An(N(SiMe3)2)3] (An = U (3), Th (4)) and [(Bim4-MeDipp/MeN)An(N(SiMe3)2)3] (An = U (5), Th (6)) were synthesized and their solid state structures were established by single-crystal X-ray diffraction analysis. The catalytic performances of complexes 3–6 towards the homo- and cross-coupling of aldehydes (Tishchenko reaction) were studied and the thorium

  苯并咪唑啉-2-亚氨基to系-（IV）络合物的新家族[（Bim 7-Me Dipp / Me N）An（N（SiMe 3）2）3 ]（An = U（3），Th（4））和[（Bim 4-Me Dipp / Me N）An（N（SiMe 3）2）3 ]（An = U（5），Th（6））合成，并通过单晶X建立其固态结构射线衍射分析。研究了配合物3 – 6对醛的均相和交叉偶联（Tishchenko反应）的催化性能，并研究了complex配合物图4和图6显示出产生相应的对称和不对称酯的中等至高活性。这些th配合物还研究了醛与醇的偶联，称为串联质子转移酯化，以及醛与三氟甲基酮之间的分子间偶联反应，表明了选择性地获得不对称酯的互补方法。这些反应的合理机制是基于化学计量研究提出的。
• Direct oxidative conversion of aldehydes and alcohols to 2-imidazolines and 2-oxazolines using molecular iodine
  作者：Midori Ishihara、Hideo Togo

  DOI：10.1016/j.tet.2006.11.077

  日期：2007.2

  Aldehydes were converted to the corresponding 2-imidazolines and 2-oxazolines in good yields by the reaction with ethylenediamine and aminoethanol, respectively, using molecular iodine and potassium carbonate. Moreover, primary alcohols were directly converted to the corresponding 2-imidazolines and 2-oxazolines via aldehydes in one-pot manner with ethylenediamine and aminoethanol, respectively, using molecular iodine and potassium carbonate. (c) 2006 Published by Elsevier Ltd.
• Tumkevicius; Navickas; Dailide, Polish Journal of Chemistry, 2006, vol. 80, # 8, p. 1377 - 1383
  作者：Tumkevicius、Navickas、Dailide

  DOI：——

  日期：——
• Organoactinides Promote the Dimerization of Aldehydes: Scope, Kinetics, Thermodynamics, and Calculation Studies
  作者：Manab Sharma、Tamer Andrea、Nigel J. Brookes、Brian F. Yates、Moris S. Eisen

  DOI：10.1021/ja105696p

  日期：2011.2.9

  Surprising catalytic activities have been found for the actinide complexes Cp*2ThMe2 (1), Th(NEtMe)(4) (2), and Me2SiCp '' Th-2(C4H9)(2)(3) toward oxygenated substrates. During the catalytic dimerization of benzaldehydes to their corresponding esters, complexes 1 and 2 gave 65 and 85% yield in 48 h, respectively, while the geometry-constrained complex 3 gave 96% yield in 24 h. Exploring the effect of substituents on benzaldehyde, it has been found that, in general, electron-withdrawing groups facilitate the reaction. Kinetic study with complexes 1 and 3 reveals that the rate of the reaction is first order in catalyst and substrate, which suggests the rate equation "rate = k[catalyst](1)-[aldehyde](1)". The activation energy of the reaction was found to be 7.16 +/- 0.40 and 3.47 +/- 0.40 kcal/mol for complexes 1 and 3 respectively, which clearly indicates the advantage of the geometry-constrained complex. Astonishing are the reactivity of the organoactinide complexes with oxygen-containing substrates, and especially the reactivity of complex 3, toward the dimerization of substrates like p-methoxybenzaldehyde, m/p-nitrobenzaldehyde, and furanaldehyde and the reactivity toward the polymerization of terephthalaldehyde. Density functional theory mechanistic study reveals that the catalytic cycle proceeds via an initially fourcentered transition state (+6 kcal/mol), followed by the rate-determining six-centered transition state (+13.5 kcal/mol), to yield thermodynamically stable products.