2,6-二硝基苯甲酸 | 603-12-3

• 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: 2,6-二硝基苯甲酸
• 英文名称: 2,6-dinitrobenzoic acid
• CAS: 603-12-3
• 化学式: C₇H₄N₂O₆
• 分子量: 212.119
• InChiKey: HKKWSIQQYJTJLW-UHFFFAOYSA-N

物化性质

• 熔点：
  202-206°C
• 沸点：
  351.93°C (rough estimate)
• 密度：
  1.7333 (rough estimate)
• 稳定性/保质期：
  性质与稳定性： 常温常压下，该物质不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2916399090
• 储存条件：
  贮存： 将密封的小容器置于密封的大容器中，并存放在阴凉、干燥处。

反应信息

• 作为反应物：
  描述：

  2,6-二硝基苯甲酸 在 盐酸 、 tin 作用下， 生成 间苯二胺
  参考文献：
  名称：

  Griess, Chemische Berichte, 1874, vol. 7, p. 1224

  摘要：

  DOI：
• 作为产物：
  描述：

  2,6-二硝基甲苯 在 permanganate(VII) ion 作用下， 生成 2,6-二硝基苯甲酸
  参考文献：
  名称：

  邻位取代的2-二乙基氨基乙基苯甲酸酯的合成作为潜在的局麻药。

  摘要：

  合成了一系列2-二乙氨基乙醇的单邻位和双邻位取代苯甲酸酯。报道了制备2,6-二氟苯甲酸和2,6-二甲基苯甲酸的改进方法。讨论了对二邻位取代苯甲酸酯的制备，并描述了一种高效的酯化这些酸的方法。

  DOI：

  10.1111/j.2042-7158.1962.tb11143.x
• 作为试剂：
  描述：

  5,5-diphenyl-5,6-dihydro-2H-1,4-oxazin-2-one 、 环戊酮 在 2,6-二硝基苯甲酸 、 C₁₀H₁₇F₃N₂O₄S 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 (R)-3-((S)-2-oxocyclopentyl)-5,5-diphenylmorpholin-2-one 、 (3S)-3-[(1R)-2-oxocyclopentyl]-5,5-diphenylmorpholin-2-one
  参考文献：
  名称：

  手性顺式二胺基有机催化剂对不对称羟醛和曼尼希反应的对映选择性中的手性酸诱导开关。

  摘要：

  挑选：通过使用单一的有机催化剂，带有或不带有非手性有机酸添加剂，已经实现了两种不同对映体产物的不对称合成（参见方案）。这些添加剂可以帮助改变催化中心的底物取向，从而导致醛醇和曼尼希产物中的有效对映异构体转化。

  DOI：

  10.1002/anie.201107239

文献信息

• Metabolism of 2,4-dinitrotoluene and 2,6-dinitrotoluene, and their dinitrobenzyl alcohols and dinitrobenzaldehydes by Wistar and Sprague-Dawley rat liver microsomal and cytosl fractions.
  作者：Masa-aki MORI、Tadashi KAWAJIRI、Michio SAYAMA、Tatsuro MIYAHARA、Hiroshi KOZUKA

  DOI：10.1248/cpb.37.1904

  日期：——

  The metabolism of 2, 4-dinitrotoluene (2, 4-DNT), 2, 4-dinitrobenzyl alcohol (2, 4-DNB), 2, 4-dinitrobenzaldehyde(2, 4-DNBAl), 2, 6-DNT, 2, 6-DNB and 2, 6-DNBAl in the microsomal and cytosol fractions prepared from unfortified male Wistar and male Sprague-Dawley (S.D.) rat livers was investigated. Data obtained by high-performance liquid chromatography (HPLC) indicated that the products of dinitrotoluenes (2, 4-DNT and 2, 6-DNT), dinitrobenzyl alcohols (2, 4-DNB and 2, 6-DNB), and dinitrobenzaldehydes (2, 4-DNBAl and 2, 6-DNBAl) in the microsomal and cytosol preparations containing nicotinamide adenine dinucleotide phosphate (NAD(P)) and reduced NAD(P)(NAD(P)H) were dinitrobenzyl alcohols (2, 4-DNB and 2, 6-DNB), dinitrobenzaldehydes (2, 4-DNBAl and 2, 6-DNBAl), and dinitrobenzoic acids (2, 4-DNBA and 2, 6-DNBA), and dinitrobenzyl alcohols (2, 4-DNB and 2, 6-DNB), respectively. From these results, it was concluded that the dinitrobenzaldehydes (2, 4-DNBAl and 2, 6-DNBAl) were intermediates in the oxidations of dinitrobenzyl alcohols (2, 4-DNB and 2, 6-DNB) to dinitrobenzoic acids (2, 4-DNBA and 2, 6-DNBA), and that the oxidations of dinitrobenzyl alcohols (2, 4-DNB and 2, 6-DNB) to dinitrobenzaldehydes (2, 4-DNBAl and 2, 6-DNBAl) and the reductions of dinitrobenzaldehydes to dinitrobenzyl alcohols (2, 4-DNB and 2, 6-DNB) were reversible The result of the consecutive oxidations of 2, 6-DNT in male Wistar rat livers, in the presence of various inhibitors suggests that oxidation of 2, 6-DNT to 2, 6-DNB is done mainly by microsomal cytochrome P-450, oxidation of 2, 6-DNB to 2, 6-DNBAl is mediated by microsomal cytochrome P-450 and nicotinamide adenine dinucleotide (NAD)-dependent alcohol dehydrogenase, oxidation of 2, 6-DNBAl to 2, 6-DNBA may be mediated by NAD-dependent aldehyde oxidase, and reduction of 2, 6-DNBAl to 2, 6-DNB may be mediated by reduced NAD(NADH)-dependent aldehyde reductase. From the comparative investigation of these reaction activities, it was found that : (a) the activity in the 2, 6-DNT oxidation to 2, 6-DNB was higher than that in the 2, 4-DNT oxidation to 2, 4-DNB in both strains, and the activity in Wistar rat was higher than that in S.D. rat; (b) the activities for the reductions of the dinitrobenzaldehydes (2, 4-DNBAl and 2, 6-DNBAl) to dinitrobenzyl alcohols (2, 4-DNB and 2, 6-DNB) were the highest, among the reactions examined, in both strains, and the reduction activity of 2, 4-DNBAl to 2, 4-DNB in Wistar rat was particularly high; (c) the activity for 2, 6-DNB oxidation to 2, 6-DNBAl was higher than that for 2, 4-DNB oxidation to 2, 4-DNBAl in both strains, and the activity in Wistar rat was higher than that in S.D. rat; (d) the activity for 2, 6-DNBAl oxidation to 2, 6-DNBA was much less than that for 2, 4-DNBAl oxidation to 2, 4-DNBA in both strains, and in particular, the activity for oxidation of 2, 6-DNBAl to 2, 6-DNBA in Wistar rat was low. The present results indicate that the metabolism of DNT isomers differs in different strains of rat.

  对未增强的雄性Wistar和雄性Sprague-Dawley (S.D.)大鼠肝脏中的微粒体和细胞质部分中的2, 4-二硝基甲苯 (2, 4-DNT)、2, 4-二硝基苄醇 (2, 4-DNB)、2, 4-二硝基苯甲醛 (2, 4-DNBAl)、2, 6-DNT、2, 6-DNB和2, 6-DNBAl的代谢进行了研究。通过高效液相色谱 (HPLC) 获得的数据表明, 在含有烟酰胺腺嘌呤二核苷酸磷酸 (NAD(P)) 和还原型NAD(P)(NAD(P)H) 的微粒体和细胞质制备物中, 二硝基甲苯 (2, 4-DNT和2, 6-DNT)、二硝基苄醇 (2, 4-DNB和2, 6-DNB) 和二硝基苯甲醛 (2, 4-DNBAl和2, 6-DNBAl) 的产物分别是二硝基苄醇 (2, 4-DNB和2, 6-DNB)、二硝基苯甲醛 (2, 4-DNBAl和2, 6-DNBAl) 和二硝基苯甲酸 (2, 4-DNBA和2, 6-DNBA), 以及二硝基苄醇 (2, 4-DNB和2, 6-DNB)。从这些结果可以得出结论, 二硝基苯甲醛 (2, 4-DNBAl和2, 6-DNBAl) 是二硝基苄醇 (2, 4-DNB和2, 6-DNB) 氧化为二硝基苯甲酸 (2, 4-DNBA和2, 6-DNBA) 的中间体, 并且二硝基苄醇 (2, 4-DNB和2, 6-DNB) 氧化为二硝基苯甲醛 (2, 4-DNBAl和2, 6-DNBAl) 和二硝基苯甲醛还原为二硝基苄醇是可逆的。在雄性Wistar大鼠肝脏中连续氧化2, 6-DNT的结果, 在存在各种抑制剂的情况下, 表明2, 6-DNT氧化为2, 6-DNB主要是由微粒体细胞色素P-450完成的, 2, 6-DNB氧化为2, 6-DNBAl是由微粒体细胞色素P-450和烟酰胺腺嘌呤二核苷酸 (NAD) 依赖性醇脱氢酶介导的, 2, 6-DNBAl氧化为2, 6-DNBA可能由NAD依赖性醛氧化酶介导, 而2, 6-DNBAl还原为2, 6-DNB可能由还原型NAD(NADH) 依赖性醛还原酶介导。从这些反应活性的比较研究中发现: (a) 2, 6-DNT氧化为2, 6-DNB的活性高于2, 4-DNT氧化为2, 4-DNB, 在两种菌株中, Wistar大鼠的活性高于S.D.大鼠; (b) 在两种菌株中, 二硝基苯甲醛 (2, 4-DNBAl和2, 6-DNBAl) 还原为二硝基苄醇 (2, 4-DNB和2, 6-DNB) 的活性是最高的, 在Wistar大鼠中2, 4-DNBAl还原为2, 4-DNB的活性尤其高; (c) 2, 6-DNB氧化为2, 6-DNBAl的活性高于2, 4-DNB氧化为2, 4-DNBAl, 在两种菌株中, Wistar大鼠的活性高于S.D.大鼠; (d) 2, 6-DNBAl氧化为2, 6-DNBA的活性远低于2, 4-DNBAl氧化为2, 4-DNBA, 特别是在Wistar大鼠中2, 6-DNBAl氧化为2, 6-DNBA的活性很低。本研究结果表明, 不同菌株大鼠中DNT异构体的代谢方式不同。
• F-18 RADIOLABELED COMPOUNDS FOR DIAGNOSING AND MONITORING KIDNEY FUNCTION
  申请人：KASINA LAILA INNOVA PHARMACEUTICALS PRIVATE LIMITED

  公开号：US20140086837A1

  公开（公告）日：2014-03-27

  The invention relates to 18 F-labeled compounds of formula (I), hydrates, isomers, or pharmaceutically acceptable salts thereof, process for their preparation and pharmaceutical compositions. The invention relates to the methods of diagnosing kidney function in humans by PET imaging.

  这项发明涉及到式(I)的18F标记化合物，以及它们的水合物、异构体或药学上可接受的盐，以及它们的制备方法和药物组合物。该发明涉及通过PET成像诊断人类肾功能的方法。
• [EN] AUTOMATED RADIOSYNTHESIS<br/>[FR] RADIOSYNTHÈSE AUTOMATISÉE
  申请人：GE HEALTHCARE LTD

  公开号：WO2011042529A1

  公开（公告）日：2011-04-14

  The present invention provides a method to obtain radiofluorinated compounds useful for in vivo imaging GABAA receptors. The method of the invention is high-yielding and may conveniently be carried out on an automated synthesizer such as FastlabTM. A further aspect of the invention is a cassette suitable for carrying out the automated method of synthesis of the invention. Novel precursor compounds useful in the method of the invention are also provided, as are a number of novel compounds obtained by the method of the invention.

  本发明提供了一种用于获取对体内成像GABAA受体有用的放射氟化合物的方法。该发明的方法产率高，并且可以方便地在诸如FastlabTM之类的自动合成仪上进行。本发明的另一个方面是一种适用于执行本发明的自动合成方法的盒子。本发明方法中有用的新型前体化合物也提供了，以及通过本发明方法获得的一些新型化合物。
• Method for Estimating S_N1 Rate Constants: Solvolytic Reactivity of Benzoates
  作者：Mirela Matić、Bernard Denegri、Olga Kronja

  DOI：10.1021/jo3013308

  日期：2012.10.19

  pentafluorobenzoate (PFB) and 2,4,6-trifluorobenzoate (TFB) leaving groups have been derived from the solvolysis rate constants of X,Y-substituted benzhydryl PFBs and TFBs measured in a series of aqueous solvents, by applying the LFER equation: log k = sf(Ef + Nf). The heterolysis rate constants of dianisylmethyl PFB and TFB, and those determined for 10 more dianisylmethyl benzoates in aqueous ethanol,

  五氟苯甲酸酯（PFB）和2,4,6-三氟苯甲酸酯（TFB）离开基团的核官能度是通过应用LFER方程从在一系列水性溶剂中测量的X，Y取代的苯甲基PFB和TFB的溶剂分解速率常数得出的：log k = s f（E f + N f）。二苯胺基甲基PFB和TFB的杂解速率常数，以及在乙醇水溶液中另外10种苯甲酰甲基苯甲酸酯的杂化速率常数，构成了一组参考苯甲酸酯，其实验ΔG with与ΔH correlat相关。（通过PCM量子化学方法计算）模型环氧环的形成。由于具有极好的相关性（r = 0.997），因此已经建立了计算取代苯甲酸酯LG的核官能度的方法，最终提供了一种测定给定溶剂中任何苯甲酸酯的S N 1反应性的方法。使用Δ ģ ⧧ VSΔ ħ ⧧的相关性，并考虑小号˚F基于相似性，已在90％，80％和70％的乙醇水溶液中确定了约70种苯甲酸酯的核官能度参数。计算得出的取代苯甲酸酯离去基团的固有壁垒
• PROCESS FOR PREPARING SUBSTITUTED AROMATIC CARBOXYLIC ACIDS
  申请人：Filer Crist N.

  公开号：US20100228048A1

  公开（公告）日：2010-09-09

  A process for preparing an aromatic carboxylic acid having a heteroatom containing substituent is provided that includes reaction in a vessel of an aromatic precursor having an aromatic core with at least one heteroatom containing substituent and at least one hydrogen extending from the core, with a haloacetonitrile under reaction conditions to form an aromatic acetonitrile with an acetonitrile moiety. The aromatic acetonitrile is exposed to an oxidizing agent under conditions to convert the acetonitrile moiety to a carboxylic acid group to prepare the aromatic carboxylic acid having the heteroatom containing substituent.

  提供了一种制备含有含杂原子取代基的芳香族羧酸的方法，包括在反应容器中将至少含有一个杂原子取代基和至少一个从核心延伸出的氢原子的芳香族前体与卤代乙腈在反应条件下反应，形成具有乙腈基团的芳香族乙腈。该芳香族乙腈在能够将乙腈基团转化为羧酸基团的条件下暴露于氧化剂，以制备含有含杂原子取代基的芳香族羧酸。