2,6-二硝基苄醇 | 96839-34-8

• 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: 2,6-二硝基苄醇
• 英文名称: 2,6-dinitrobenzyl alcohol
• 英文别名: (2,6-dinitrophenyl)methanol
• CAS: 96839-34-8
• 化学式: C₇H₆N₂O₅
• mdl: MFCD01657414
• 分子量: 198.135
• InChiKey: JOFAFRXWWUXIEE-UHFFFAOYSA-N

物化性质

• 熔点：
  94 °C
• 沸点：
  345.8±27.0 °C(Predicted)
• 密度：
  1.560±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2906299090

反应信息

• 作为反应物：
  描述：

  2,6-二硝基苄醇 生成 2-Nitro-6-nitroso-benzaldehyde
  参考文献：
  名称：

  可光活化的荧光团。1.邻硝基苄基猝灭的荧光氨基甲酸酯的合成和光活化。

  摘要：

  描述了新型荧光探针，可光活化的荧光团（PAF）的合成和光活化。本文中描述的PAF由荧光性芳香胺组成，这些胺通过氨基甲酸酯键与取代的硝基苄基猝灭发色团偶联。通过分子内的光-氧化还原反应发生光活化，将邻硝基苄基转化为不稳定的邻硝基亚硝基苯甲醛半缩醛，该片段断裂并失去CO 2释放出荧光胺。还报道了光活化量子产率。

  DOI：

  10.1016/0040-4039(88)80017-0
• 作为产物：
  描述：

  2,6-二硝基甲苯 在 sodium chlorite 、 N-溴代丁二酰亚胺(NBS) 、 2-甲基-2-丁烯 、 mercurous nitrate 、 溶剂黄146 、 三乙胺 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙二醇二甲醚 、 水 为溶剂， 反应 27.0h， 生成 2,6-二硝基苄醇
  参考文献：
  名称：

  一种将芳香族甲基直接氧化成醛和羧酸的简便方法

  摘要：

  连接到芳环上的甲基氧化生成醛和/或羧酸，是有机化学中的常见反应。获得酸的经典方法是用强氧化剂直接氧化，并已在许多条件下进行。l 但是有局限性，我们对连接到多环杂环上的甲基的经验是，环系统的大量分解伴随着靶向氧化。在转化为醛的各种间接方法中，下面显示的先前报道的 Z 序列具有吸引人的特征。ACHJ ArCHZBr ArCH20N& ACHO

  DOI：

  10.1080/00304940309355366

文献信息

• Resist materials
  申请人：AT&T Bell Laboratories

  公开号：US05200544A1

  公开（公告）日：1993-04-06

  A class of resist compositions sensitive to deep ultraviolet radiation includes a resin sensitive to acid and a composition that generates acid upon exposure to such radiation. A group of nitrobenzyl materials is particularly suitable for use as the acid generator.

  此类抗蚀剂组合物对深紫外光敏感，包括对酸敏感的树脂和一种在暴露于此类辐射时产生酸的组合物。特别是，硝基苄基材料适合用作酸发生剂。
• 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。
• Synthesis of Pyridinium Dinitrobenzyl Sulfates and Potassium (Dinitrobenzyl .BETA.-D-Glucopyranosid)Uronates.
  作者：Masa-aki MORI、Masahiro DOHRIN、Michio SAYAMA、Miki SHOJI、Masami INOUE、Hiroshi KOZUKA

  DOI：10.1248/cpb.46.145

  日期：——

  Sulfates and glucuronides of 2, 4-dinitrobenzyl alcohol 1a and 2, 6-dinitrobenzyl alcohol 1b, which are major or putative metabolites of 2, 4-dinitrotoluene (2, 4-DNT) and 2, 6-dinitrotoluene (2, 6-DNT), were synthesized from 1a and 1b by reaction with pyridinium sulfonate and methyl (2, 3, 4-tri-O-acetyl-α-D-glucopyranosyl)uronate bromide 3, respectively, as their pyridinium salts (2a, 2b) and potassium salts (6a, 6b). These conjugates are important for the study of the carcinogenicity of 2, 4-DNT and 2, 6-DNT.

  2, 4-二硝基苄醇1a和2, 6-二硝基苄醇1b的主要或假定代谢物，即它们的硫酸酯和葡糖苷酸，是通过1a和1b分别与吡啶硫酸酯和甲基（2, 3, 4-三-O-乙酰基-α-D-吡喃葡萄糖苷酸）溴化物3反应合成的，形成它们的吡啶盐（2a, 2b）和钾盐（6a, 6b）。这些结合物对于研究2, 4-二硝基甲苯（2, 4-DNT）和2, 6-二硝基甲苯（2, 6-DNT）的致癌性至关重要。
• [EN] DYE COMPOSITIONS, METHODS OF PREPARATION, CONJUGATES THEREOF, AND METHODS OF USE<br/>[FR] COMPOSITIONS DE COLORANT, PROCÉDÉS DE PRÉPARATION, CONJUGUÉS ASSOCIÉS, ET PROCÉDÉS D'UTILISATION
  申请人：UNIV CORNELL

  公开号：WO2013109859A1

  公开（公告）日：2013-07-25

  Dye compounds of the formula (1) wherein A is a protective agent group that has a characteristic of modifying the singlet-triplet occupancy of the shown cyanine moiety, and M is a reactive crosslinking group or a group that can be converted to a reactive crosslinking group. Methods for synthesizing the dye compounds and applications for their use are also described.

  化合物的染料的公式（1），其中A是一种保护剂基团，具有修改所示青菁基团的单三态占据特性，而M是一种反应性交联基团或可转化为反应性交联基团的基团。还描述了合成染料化合物的方法以及它们的用途。
• Photogeneration of organic bases from o-nitrobenzyl-derived carbamates
  作者：James F. Cameron、Jean M. J. Frechet

  DOI：10.1021/ja00011a038

  日期：1991.5

  that control their quantum-efficient transformation into free amines or diamines have been investigated. The basic design involves the protection of amines with photolabile [(o-nitrobenzyl)oxy]carbonyl groups or α-substituted analogues. The resulting protected amines owe their light sensitivity to the classical o-nitrobenzyl photorearrangement and cleanly liberate free amine in both the solid state

  已经研究了有机碱的新型光前体的设计以及控制其量子效率转化为游离胺或二胺的空间和电子因素。基本设计涉及用光不稳定 [(o-nitrobenzyl)oxy] 羰基或 α-取代类似物保护胺。所得受保护的胺的光敏感性归功于经典的邻硝基苄基光重排，并且在用低于 400 nm 的紫外光照射时，可以在固态和溶液中干净地释放游离胺。探索了几种设计，其中光活性中心的结构有系统地变化，以研究各种空间和电子效应的影响。在所有情况下，