2-硝基苯硒酸 | 56790-59-1

• 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-硝基苯硒酸
• 英文名称: 2-nitrobenzeneseleninic acid
• 英文别名: o-nitrobenzeneseleninic acid；Benzeneseleninic acid, 2-nitro-
• CAS: 56790-59-1
• 化学式: C₆H₅NO₄Se
• 分子量: 234.07
• InChiKey: LNJFIDXLARAFNQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.29
• 重原子数：
  12
• 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：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-硝基苯硒酸 在 偶氮二异丁腈 、 三乙胺 作用下， 以 氯仿 为溶剂， 生成 (Z)-3-chloro-2-((o-nitrophenyl)seleno)-1-(p-toluenesulfonyl)-2-propene
  参考文献：
  名称：

  Asymmetric selenoxide elimination leading to chiral allenic sulfones

  摘要：

  Asymmetric oxidation of some aryl vinyl selenides (3) with Sharpless (A-C), modified Sharpless (D) or David oxidants (E-G) resulted in the formation of chiral allenic sulfones 5 of up to 42% enantiomeric excess (ee) via double asymmetric induction, i.e., asymmetric oxidation to selenoxide followed by its asymmetric elimination. The nature of aryl group of the selenides 3 showed a remarkable effect upon the ee of the product: o-nitrophenyl group (a) gave the highest ee, followed by o,p-dinitrophenyl (b), o-(trifluoromethyl)phenyl (e), and o-methoxyphenyl (f) groups, while phenyl (e) and 2-pyridyl (d) groups were not effective at all. The effects of aryl groups were kinetically analyzed by comparing the rate constants of both steps (k1 for oxidation step and k2 for elimination step) which were determined by H-1-NMR analysis of the concentration of 3, the intermediate selenoxides 4, and 5. As a result, it was disclosed that the ratio of these rate constants (k1/k2) Was closely related to the ee of the product; the smaller the ratio is, the larger the ee becomes.

  DOI：

  10.1021/jo00066a023
• 作为产物：
  描述：

  2-nitro-benzeneselenenyl bromide 在 双氧水 、 溶剂黄146 、 苯 作用下， 生成 2-硝基苯硒酸
  参考文献：
  名称：

  Rheinboldt; Giesbrecht, Justus Liebigs Annalen der Chemie, 1950, vol. 568, p. 198,212

  摘要：

  DOI：
• 作为试剂：
  描述：

  3-甲基-2-丁醇 、 4-bromobenzaldehyde oxime 在 2-硝基苯硒酸 、 双氧水 作用下， 反应 4.0h， 以53%的产率得到1,1-dimethylpropyl 4-bromobenzoate
  参考文献：
  名称：

  Oxidative Conversion of Aldoximes into Carboxylic Acid Esters

  摘要：

  Aromatic and aliphatic aldoximes or their O-methyl ethers can be efficiently converted into the corresponding carboxylic acid esters by treatment with an alcoholic solution of 30% hydrogen peroxide in the Presence of catalytic amounts of 2-nitrobenzeneseleninic acid. Primary alcohols give excellent to good yields, secondary ones - good to moderate, but with tertiary alcohols no esterification is obserwed.

  DOI：

  10.1080/00397919208021316

文献信息

• The Baeyer-Villiger Oxidation of Aromatic Aldehydes and Ketones with Hydrogen Peroxide Catalyzed by Selenium Compounds. A Convenient Method for the Preparation of Phenols
  作者：Ludwik Syper

  DOI：10.1055/s-1989-27183

  日期：——

  A series of organoselenium compounds was investigated as activators of hydrogen peroxide in the Baeyer-Villiger oxidation. As a result, a convenient and cheap method for transformation of aromatic aldehydes, having polycondensed ring systems or electron-donating substituents, and polymethoxy derivatives of acetophenone, into phenols was elaborated. This method utilizes hydrogen peroxide activated by areneseleninic acids, as oxidizing agent.

  一系列有机硒化合物被研究作为过氧化氢在拜耳-维利格氧化反应中的活化剂。结果发现，这是一种方便且经济的转化具有聚合环系或供电子取代基的芳香醛、乙酰苯的多甲氧基衍生物为酚类的方法。该方法使用由芳硒酸活化的过氧化氢作为氧化剂。
• Modelling the Inhibition of Selenoproteins by Small Molecules Using Cysteine and Selenocysteine Derivatives
  作者：Kishorkumar M. Reddy、Govindasamy Mugesh

  DOI：10.1002/chem.201901363

  日期：——

  cysteine‐ and selenocysteine‐containing proteins. CDNB has been used extensively to determine the activity of glutathione S‐transferase and to deplete glutathione (GSH) in mammalian cells. Also, CDNB has been shown to irreversibly inhibit thioredoxin reductase (TrxR), a selenoenzyme that catalyses the reduction of thioredoxin (Trx). Mammalian TrxR has a C‐terminal active site motif, Gly‐Cys‐Sec‐Gly, and

  基于小分子的亲电子化合物，例如1-氯-2-，4-二硝基苯（CDNB）和1-氯-4-硝基苯（CNB）被用作半胱氨酸和硒代半胱氨酸蛋白的抑制剂。CDNB已被广泛用于确定谷胱甘肽S的活性转移酶并耗尽哺乳动物细胞中的谷胱甘肽（GSH）。而且，已证明CDNB不可逆地抑制硫氧还蛋白还原酶（TrxR），这是一种催化硫氧还蛋白（Trx）还原的硒酶。哺乳动物TrxR具有C端活性位点基序Gly-Cys-Sec-Gly，半胱氨酸和硒代半胱氨酸残基都可能是亲电子试剂的靶标。在本文中，我们报告了一系列半胱氨酸和硒代半胱氨酸衍生物的稳定性，这些衍生物可被视为硒代酶-抑制剂复合物的模型。我们证明这些衍生物与H 2 O 2反应生成相应的亚硒酸盐，将其自发消除以生成脱氢丙氨酸。相反，半胱氨酸衍生物对这种消除反应是稳定的。我们还首次证明了从硒代半胱氨酸衍生物中消除的芳基硒物种通过在GSH存在下催化H 2 O 2的还原而表现出
• Benzeneperoxyseleninic acids-synthesis and properties
  作者：Ludwik Syper、Jacek Młochowski

  DOI：10.1016/s0040-4020(01)89946-4

  日期：1987.1
• Behaghel; Seibert, Chemische Berichte, 1933, vol. 66, p. 708,716
  作者：Behaghel、Seibert

  DOI：——

  日期：——
• Electrophilic organic selenium reagents—protonated seleninic acids as precursors for unsymmetrical aromatic selenides
  作者：Nicolai Stuhr-Hansen、Theis Ivan Sølling、Lars Henriksen

  DOI：10.1016/j.tet.2011.02.004

  日期：2011.4

  Arylselenylations of methylbenzenes, methoxybenzenes and thiophene were smoothly achieved with selenenium ions generated by comproportionation of 1:1 mixtures of p-toluenesulfonic acid salts of seleninic acids and the corresponding diselenides. A series of p-toluenesulfonic salts of seleninic acids were prepared by hydrogen peroxide oxidation of the corresponding diselenides in the presence of p-toluenesulfonic acid. Novel 2-(organylseleno)thiophenes were obtained by heating the protonated seleninic acids with a 50-fold excess of thiophene in glacial acetic acid. (C) 2011 Published by Elsevier Ltd.