1-(溴甲基)-3,5-二硝基苯 | 137570-75-3

• 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: 1-(溴甲基)-3,5-二硝基苯
• 英文名称: 1-bromomethyl-3,5-dinitrobenzene
• 英文别名: 3,5-dinitrobenzylbromide；1-(Bromomethyl)-3,5-dinitrobenzene
• CAS: 137570-75-3
• 化学式: C₇H₅BrN₂O₄
• 分子量: 261.032
• InChiKey: PVJNFIVPIQXQLZ-UHFFFAOYSA-N

物化性质

• 熔点：
  65-66 °C
• 沸点：
  177 °C
• 密度：
  1.830±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 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-(溴甲基)-3,5-二硝基苯 在 silver nitrate 、 sodium iodide 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 12.0h， 生成 2,4-二硝基-1-(硝基甲基)苯
  参考文献：
  名称：

  Solvent Effects on Proton Transfer Reactions:  Benzoate Ion Promoted Deprotonation Reactions of Arylnitromethanes in Methanol Solution

  摘要：

  Second-order rate constants and equilibrium constants have been determined for the benzoate ion promoted deprotonation reactions of (m-nitrophenyl)nitromethane, (p-nitrophenyl)nitromethane, and (3,5-dinitrophenyl)nitromethane in methanol solution. The pK(a) values for the arylnitromethanes in methanol are the following: pK(a) = 10.9, 10.5, and 9.86 for (m-nitrophenyl)-nitromethane, (p-nitrophenyl)nitromethane, and (3,5-dinitrophenyl)nitromethane, respectively, relative to benzoic acid (pK(a) = 9.4). A Bronsted beta(B) value of 0.50 and alpha(CH) value of 1.31 have been calculated for the 3,4-dimethylbenzoate, benzoate, m-bromobenzoate, and 3,4-dichlorobenzoate ion promoted reactions of(3,5-dinitrophenyl)nitromethane, and for the benzoate ion promoted reactions of (m-nitrophenyl)nitromethane, (p-nitrophenyl)nitromethane, and (3,5-dinitrophenyl)nitromethane, respectively. The log of the intrinsic rate constants for benzoate ion promoted deprotonations of (m-nitrophenyl)nitromethane, (p-nitrophenyl)nitromethane, and (3,5-dinitrophenyl)nitromethane are 0.0212, 0.270, and 0.877, respectively. These values are 6.3 x 10(4), 2.0 x 10(4), and 2.5 x 10(4) times lower than for the same reactions in acetonitrile solution. The transfer activity coefficient from methanol to acetonitrile solution, log (M) gamma(AN), for (m-nitrophenyl)nitromethyl anion (3.6) and (m-nitrophenyl)nitromethane (-1.0) have been calculated. The solvent effect on these reactions in methanol and acetonitrile, two solvents with similar dielectric constants, are analyzed within the framework of the Principal of Nonperfect Synchronization. The results suggest that the observed solvent effect is a result of an imbalanced transition state (i.e., PNS effects), and a stronger transition state hydrogen bond between the carbon acid and benzoate ion in acetonitrile than in methanol solution.

  DOI：

  10.1021/jo970409f
• 作为产物：
  描述：

  3,5-二硝基甲苯 在 溴 作用下， 生成 1-(溴甲基)-3,5-二硝基苯
  参考文献：
  名称：

  Kroehnke; Schmeiss, Chemische Berichte, 1939, vol. 72, p. 440,445

  摘要：

  DOI：

文献信息

• 2-((3,5-Dinitrobenzyl)thio)quinazolinones: Potent Antimycobacterial Agents Activated by Deazaflavin (F₄₂₀)-Dependent Nitroreductase (Ddn)
  作者：Yanlin Jian、He Eun Forbes、Fabian Hulpia、Martijn D. P. Risseeuw、Guy Caljon、Hélène Munier-Lehmann、Helena I. M. Boshoff、Serge Van Calenbergh

  DOI：10.1021/acs.jmedchem.0c01374

  日期：2021.1.14

  substituents in positions 2 and 4 of the previously synthesized but yet undisclosed 5-cyano-4-(methylthio)-2-arylpyrimidin-6-ones 4, ring closure, and further optimization led to the identification of the potent antitubercular 2-thio-substituted quinazolinone 26. Structure–activity relationship (SAR) studies indicated a crucial role for both meta-nitro substituents for antitubercular activity, while the introduction

  交换先前合成但尚未公开的 5-cyano-4-(methylthio)-2-arylpyrimidin-6-ones 4 的 2 和4位取代基、闭环和进一步优化导致鉴定出有效的抗结核药物 2-硫代喹唑啉酮26。结构-活性关系（SAR）研究表明，两个间硝基取代基在抗结核活性中发挥着至关重要的作用，而在喹唑啉酮核心上引入极性取代基可以减少牛血清白蛋白（BSA）的结合（ 63c，63d）。虽然大多数测试的喹唑啉酮类化合物没有表现出针对 MRC-5 的细胞毒性，但通过 Ames 测试发现最有效的化合物26具有诱变性。该类似物对结核分枝杆菌胸苷酸激酶（3-氰基吡啶酮的靶标，位于当前类似物的基础上）表现出中等的抑制效力，表明本发明的S-取代的硫代喹唑啉酮的全细胞抗分枝杆菌活性可能是由于调节替代或额外目标。观察到受辅因子 F 420生物合成 ( fbiC )、辅因子还原 ( fgd ) 或去氮黄素依赖性硝基还原酶活性
• Efficient approach for the design of effective chiral quaternary phosphonium salts in asymmetric conjugate additions
  作者：Seiji Shirakawa、Atsuyuki Kasai、Takashi Tokuda、Keiji Maruoka

  DOI：10.1039/c3sc22130j

  日期：——

  approach for the design of chiral quaternary phosphonium bromides as chiral phase-transfer catalysts was demonstrated. A catalyst library of phosphonium salts with various structures was readily constructed using commercially available chiral phosphines as catalyst precursors, and an optimized catalyst was successfully applied to highly enantioselective conjugate additions under base-free phase-transfer

  证明了一种设计手性季chi溴化物作为手性相转移催化剂的有效方法。使用市售的手性膦作为催化剂前体可以轻松构建具有各种结构的phospho盐的催化剂库，并且在无催化剂的低相转移条件下，将优化的催化剂成功应用于高对映选择性共轭物的加成。
• Highly Selective Aldose Reductase Inhibitors. II. Optimization of the Aryl Part of 3-(Arylmethyl)-2,4,5-trioxoimidazolidine-1-acetic Acids.
  作者：Takayuki KOTANI、Akira ISHII、Yasuhiro NAGAKI、Yoshio TOYOMAKI、Hisashi YAGO、Seishi SUEHIRO、Nobuhisa OKUKADO、Kaoru OKAMOTO

  DOI：10.1248/cpb.45.297

  日期：——

  Accumulation of intracellular sorbitol, the product of glucose reduction catalyzed by aldose reductase (AR) [EC 1.1.1.21], is thought to be the main culprit in the development of diabetic complications. A series of 3-arylalkyl-2,4,5-trioxoimidazolidine-1-acetic acids was prepared and tested for inhibitory activities towards AR and aldehyde reductase (ALR) [EC 1.1.1.2]. These derivatives showed strong

  醛糖还原酶（AR）[EC 1.1.1.21]催化的葡萄糖还原产物胞内山梨醇的积累被认为是糖尿病并发症发展的主要元凶。制备了一系列3-芳基烷基-2,4,5-三氧代咪唑烷-1-乙酸，并测试了其对AR和醛还原酶（ALR）的抑制活性[EC 1.1.1.2]。这些衍生物显示出对AR的强抑制活性，而没有明显抑制ALR。特别地，具有3-硝基苯基，4-氯-3-硝基苯基和氯取代的苯并噻唑基作为芳基部分的化合物显示出强大的AR抑制活性。氯取代的苯并噻唑基化合物的AR选择性超过5,000倍。
• [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。
• Design, Synthesis and Antitubercular Activity of 2-(Benzylthio)-1H-benzo[d]imidazoles
  作者：Raoní Rambo、Etienne Waldow、Bruno Abaddi、Maiele Silveira、Adilio Dadda、Nathalia Sperotto、Cristiano Bizarro、Luiz Augusto Basso、Pablo Machado

  DOI：10.21577/0103-5053.20210040

  日期：——

  Using molecular simplification and molecular hybridization approaches, a series of 2-(benzylthio)-1H-benzo[d]imidazoles was synthesized and evaluated as in vitro inhibitors of Mycobacterium tuberculosis (M. tuberculosis) growth. Compounds 6p and 6z were considered the lead compounds from this series of molecules, with minimal inhibitory concentration (MIC) values of 6.9 and 3.8 μM against M. tuberculosis

  利用分子简化和分子杂化方法，合成了一系列2-(苄硫基)-1H-苯并[d]咪唑类化合物，并作为体外抑制结核分枝杆菌(M. tuberculosis)生长的试剂进行评估。该系列化合物中的6p和6z被认为是领先的化合物，对M. tuberculosis H37Rv的最小抑制浓度（MIC）分别为6.9和3.8μM。此外，这些领先的化合物对多药耐药菌株也具有活性，并且对Vero和HepG2细胞没有明显毒性，这是通过3-(4,5-二甲基噻唑-2-基)-2,5-二苯基四唑溴化物（MTT）和中性红试验得出的。最后，这些化合物具有良好的水溶性和高的血浆稳定性。这些数据表明，这一类分子可能为未来开发新的抗结核病药物候选物提供了可能性。