1-Deuterio-2,4-dinitrobenzene | 163431-90-1

• 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: 1-Deuterio-2,4-dinitrobenzene
• 英文别名: 1-D-2,4-dinitrobenzene；1-deuterio-2,4-dinitro-benzene
• CAS: 163431-90-1
• 化学式: C₆H₄N₂O₄
• 分子量: 169.101
• InChiKey: WDCYWAQPCXBPJA-VMNATFBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Deuterio-2,4-dinitrobenzene 在 叔丁基过氧化氢 、 potassium tert-butylate 作用下， 以 氨 为溶剂， 生成 2,4-二硝基酚 、
  参考文献：
  名称：

  Hydroxylation of Nitroarenes with Alkyl Hydroperoxide Anions via Vicarious Nucleophilic Substitution of Hydrogen

  摘要：

  Carbo- -and heterocyclic nitroarenes react with anions of tert-butyl and cumyl hydroperoxides in the presence of strong bases to form substituted o- and p-nitrophenols. The reaction usually proceeds in high yields and is of practical value as a method of synthesis and manufacturing of nitrophenols. Orientation of the hydroxylation can be controlled to a substantial extent by selection of the proper conditions. Basic mechanistic features of this process were clarified.

  DOI：

  10.1021/jo970726m
• 作为产物：
  描述：

  2,4-二硝基苯胺 在 亚硝酸丁酯 、 N,N-二甲基甲酰胺-d7 、 三氟化硼乙醚 、 iron(II) sulfate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 7.83h， 生成 1-Deuterio-2,4-dinitrobenzene
  参考文献：
  名称：

  Efficient Catalysis of Hydrodediazoniations in Dimethylformamide

  摘要：

  For hydrodediazoniations (the replacement of a diazo group by hydrogen) in DMF, several substances act as catalysts through their ability to serve as electron donors and initiate free-radical reactions. A general procedure has been developed in which FeSO4 speeds the conversion and leads to higher yields. Trapping experiments demonstrated the presence of free-radical intermediates. N,N-Dimethylacetamide was found to rival DMF as a source of hydrogen atoms.

  DOI：

  10.1021/jo00111a032

文献信息

• Efficient synthesis of nebularine and vidarabine via dehydrazination of (hetero)aromatics catalyzed by CuSO₄in water
  作者：Ran Xia、Ming-Sheng Xie、Hong-Ying Niu、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1039/c3gc41658e

  日期：——

  A simple dehydrazination reaction has been achieved in the presence of a catalytic amount of CuSO4 for the first time. With CuSO4 (2 mol%) as a catalyst and water as a solvent, the dehydrazination products were obtained in good yields (66–95%). Moreover, the drugs nebularine and vidarabine were afforded successfully, and vidarabine could be produced on a 0.923 kg scale, which shows good potential for industrial applications.

  首次在催化量的CuSO4存在下实现了一步简单的脱氢反应。以CuSO4 (2 mol%)为催化剂，水为溶剂，脱氢产物获得了良好的产率（66-95%）。此外，成功合成了药物 nebularine 和 Vidarabine，并且 Vidarabine 可在0.923公斤规模生产，显示出良好的工业应用潜力。
• CAN-Mediated Oxidation of Electron-Deficient Aryl and Heteroaryl Hydrazines and Hydrazides
  作者：Bogdan Štefane、Slovenko Polanc

  DOI：10.1055/s-2007-1072749

  日期：2008.5

  Aryl and heteroaryl hydrazines and hydrazides were successfully oxidised using CAN, deriving dehydrazinated products. The reaction pathway strongly depends on the nature of the substrate, resulting in the formation of hydrocarbons or alkoxy derivatives. When deuterated solvents such as methanol-d 4 or acetonitrile-d 3 were used, a regiospecific incorporation of deuterium was achieved.

  芳基和杂芳基肼及肼酰胺成功地通过CAN被氧化，生成去肼化产物。反应途径强烈依赖于底物的性质，导致烃或烷氧衍生物的形成。当使用氘化溶剂，如氘代甲醇（methanol-d₄）或氘代乙腈（acetonitrile-d₃）时，实现了氘的区域特异性结合。
• Deuteriodediazoniation: A general method for the replacement of a diazonium group by deuterium
  作者：Frederick W. Wassmundt、William F. Kiesman

  DOI：10.1002/jlcr.2580360311

  日期：1995.3

  Aromatic amino groups are replaced with deuterium via a diazonium salt intermediate. Dimethylformamide-d7 is the deuterium donor in this mild replacement method that yields aromatic-d1 products in high isotopic purity. The presence of methyl groups lowers the isotopic purity of the products.

  芳香氨基团通过重氮盐中间体被氘替换。在这种温和的替换方法中，二甲基甲酰胺-d7是氘的供体，产物为高同位素纯度的芳香-d1化合物。甲基的存在降低了产物的同位素纯度。
• Direct methoxylation of nitroarenes and nitroazaarenes with alkaline methoxides via nucleophilic displacement of an aromatic hydrogen atom
  作者：Takehiko Kawakami、Hitomi Suzuki

  DOI：10.1039/a909675b

  日期：——

  at room temperature results in the displacement of an aromatic hydrogen at the 4-position by methoxide, affording 2,4-dinitroanisole and its 6-substituted derivatives, respectively, in low to moderate yield. In contrast, an equimolar reaction under similar conditions leads to the replacement of the nitro group in preference to the ring hydrogen. The reaction does not take place with lithium methoxide

  治疗 1,3-二硝基苯 以及含有过量钾或 甲醇钠 在 1,3-二甲基咪唑啉-2- （DMI）在室温下会导致甲醇中4位芳香族氢的置换，得到 2,4-二硝基苯甲醚分别以低到中等的收率得到它的6-取代衍生物。相反，在类似条件下的等摩尔反应导致取代硝基优先于环氢。反应不会与甲醇锂作为基础。单声道和二硝基萘和硝基喹啉经历氢原子的类似位移的位置处的邻位或对位的硝基，以中等收率得到相应的甲氧基衍生物。缓慢添加硝基化合物 大大超过 甲醇钾已经发现在氧气气氛下在高温下提高转化率并提高产物收率。在产品分配的基础，以及作为动力学同位素效应ķ ħ / ķ d  = 2.1，甲醇通过离子的环氢原子的直接置换已经以的速度决定释放方面解释本位α-氢原子为一种质子 来自最初形成的迈森海默加合物。
• Efficient Catalysis of Hydrodediazoniations in Dimethylformamide
  作者：Frederick W. Wassmundt、William F. Kiesman

  DOI：10.1021/jo00111a032

  日期：1995.3

  For hydrodediazoniations (the replacement of a diazo group by hydrogen) in DMF, several substances act as catalysts through their ability to serve as electron donors and initiate free-radical reactions. A general procedure has been developed in which FeSO4 speeds the conversion and leads to higher yields. Trapping experiments demonstrated the presence of free-radical intermediates. N,N-Dimethylacetamide was found to rival DMF as a source of hydrogen atoms.