5,5'-dimethyl-2,2'-dipyridyl diselenide | 496043-96-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5,5'-dimethyl-2,2'-dipyridyl diselenide
• 英文别名: bis(5-methyl-2-pyridyl) diselenide；bis(5-methyl-2-pyridyl)diselenide；Pyridine, 2,2'-diselenobis[5-methyl-；5-methyl-2-[(5-methylpyridin-2-yl)diselanyl]pyridine
• CAS: 496043-96-0
• 化学式: C₁₂H₁₂N₂Se₂
• 分子量: 342.161
• InChiKey: ACTOKZONZCZLPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.37
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,5'-dimethyl-2,2'-dipyridyl diselenide 在 溴 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到5-methyl-2-pyridylselenenylbromide
  参考文献：
  名称：

  A Study on the Antioxidant Activity of Pyridylselenium Compounds and their Slow Release from Poly(acrylamide) Hydrogels

  摘要：

  The antioxidant activity of pyridylselenium compounds has been evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical and nitric oxide (NO) scavenging methods. Pyridylselenium compounds have shown far superior (100-1000 times) antioxidant property than ebselen. The control release of bis(2-pyridyl) diselenide from poly(acrylamide) hydrogels has been studied in order to evaluate its release mechanism and diffusion coefficient. The later study also demonstrates that the pyridylselenium loading into the polymer matrix increases the magnitude and the rate of the radical scavenging activity of the poly(acrylamide) hydrogels.

  DOI：

  10.1080/10426507.2013.844143
• 作为产物：
  描述：

  在 水 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以3.8 g的产率得到5,5'-dimethyl-2,2'-dipyridyl diselenide
  参考文献：
  名称：

  Synthesis, characterization and X-ray structure of 3,4-lutidinyl-, 3-/4-picolyl- and pyridylselenium compounds

  摘要：

  Bis(4,5-dimethyl-2-pyridyl)-, bis(5-methyl-2-pyridyl)- and bis(4-methyl-2-pyridyl) diselenide have been synthesized directly from 3,4-lutidine (1a), 3-picoline (1b) and 4-picoline (1c) respectively via BF3 aided lithiation reaction. The lithiation of 3,4-lutidinium-, 3- and 4-picolinium-BF3 adduct (2a/2b/2c) gives the corresponding carbanion (3a/3b/3c) which on subjecting to selenium insertion reaction followed by aerial oxidation affords the related diselenide in good yield. Reaction of BF3 complexed pyridylselenolate anion (4a/4b/4c) with diiodomethane gives the corresponding bis(2-pyridylseleno)methane. The dilithiation of 4-picolinium-/pyridinium-BF3 adduct (2c/2d) followed by reaction with 2.2 equiv. of selenium and iodomethane affords the related 2,6-bis(methylselenenyl)pyridine and 2-(methylselenenyl)pyridine in varying proportions. Preparation of tris(methylselenenyl) derivatives of 1a and 1c have been given in the present study. LiAlH4 has also been utilized to synthesize unsymmetrical monoselenides from the corresponding diselenides. Single crystal X-ray studies of bis(4,5-dimethyl-2-pyridyl) diselenide (5a), 3,4-dimethyl-2,6-bis(methylselenenyl)pyridine (9a), 4-methyl-2,6-bis(methylselenenyl)pyridine (9c), 2,6-bis(methylselenenyl)pyridine (9d) and 4-methyl-2,6-bis(methylselenenyl)-4-(methylselenenylmethyl)pyridine (12a) have also been carried out. The crystal data of these compounds reveals that the instances of Se center dot center dot center dot Se secondary interactions decreases with the increase in the number of methyl group attached to the pyridine ring. (C) 2012 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2012.03.043

文献信息

• A novel and convenient synthesis towards 2-pyridylselenium compounds: X-ray crystal structure of 4,4′-dimethyl-2,2′-dipyridyl diselenide and tris(2-pyridylseleno)methane
  作者：K.K Bhasin、Jaspreet Singh

  DOI：10.1016/s0022-328x(02)01627-3

  日期：2002.9

  hydrazine hydrate in sodium hydroxide reacts in situ with 2-bromopyridines to afford the title compounds in good to excellent yields. Hydrazine hydrate readily cleaves the selenium-selenium bond in these diselenides to generate 2-pyridylselenolate anion, which reacts with halomethanes to afford 2-pyridylseleno methanes. X-ray crystal structure of 4,4′-dimethyl-2,2′-dipyridyl diselenide (4) and tris(2-pyridylseleno)methane

  通过使用非低温条件的简单方便的方法制备了各种2,2'-二吡啶基二硒化物。通过用100％氢氧化钠在氢氧化钠中还原元素硒而形成的二硒化物阴离子Se 2 2-与二溴吡啶原位反应，以良好的收率获得优异的标题化合物。水合肼易于在这些二硒化物中裂解硒-硒键，生成2-吡啶基硒烯酸酯阴离子，其与卤代甲烷反应生成2-吡啶基硒代甲烷甲烷。描述了4,4'-二甲基-2,2'-二吡啶基二硒化物（4）和三（2-吡啶基硒代）甲烷（10）的X射线晶体结构。
• A mechanistic study of the synthesis, single crystal X-ray data and anticarcinogenic potential of bis(2-pyridyl)selenides and -diselenides
  作者：Jaspreet S. Dhau、Avtar Singh、Amritpal Singh、Neha Sharma、Paula Brandão、Vítor Félix、Baljinder Singh、Vishal Sharma

  DOI：10.1039/c5ra15577k

  日期：——

  A mechanistic study on LiAlH₄ assisted scission of C–Se bond in bis(2-pyridyl)diselenides leading to bis(2-pyridyl)selenides generation has been presented.

  一项关于LiAlH₄辅助裂解双(2-吡啶基)二硒化物中C-Se键的机理研究已经呈现出双(2-吡啶基)硒化物生成。
• Preparation and Characterization of Methyl Substituted 2,2′-Dipyridyl Diselenides, 2,2′-Dipyridyl Ditellurides, and Their Derivatives
  作者：K. K. Bhasin、V. K. Jain、H. Kumar、Shweta Sharma、S. K. Mehta、Jaspreet Singh

  DOI：10.1081/scc-120016362

  日期：2003.1.4

  Abstract A number of methyl substituted 2,2′-dipyridyl diselenides and -ditellurides have been prepared. Effect of the solvent and the substituents on the rate of these reactions have also been studied. The preparation of 2-methylseleno/telluro picolines by reductive cleavage of the diselenides and ditellurides and by one pot reaction using n-BuLi at −78°C in THF is reported.

  摘要 已经制备了许多甲基取代的 2,2'-二吡啶基二硒化物和二碲化物。还研究了溶剂和取代基对这些反应速率的影响。报道了通过还原裂解二硒化物和二碲化物以及在 -78°C 下在 THF 中使用 n-BuLi 进行一锅反应制备 2-甲基硒/碲甲基吡啶甲啉。
• Synthesis and characterization of novel pyridyl/naphthyl/(diphenyl)methylseleno substituted alkanoic acids: X-ray structure of 2-pyridylselenoethanoic acid, 2-naphthylselenoethanoic acid and 2-(diphenyl)methylselenoethanoic acid
  作者：Aman Bhalla、Yogesh Nagpal、Rajeev Kumar、S.K. Mehta、K.K. Bhasin、S.S. Bari

  DOI：10.1016/j.jorganchem.2008.10.020

  日期：2009.1

  sodium borohydride in ethanol. The ethyl pyridyl/naphthyl/(diphenyl)methylseleno substituted alkanoates (8–13) on basic hydrolysis and subsequent acidification afford pyridyl/naphthyl/(diphenyl) methylseleno substituted alkanoic acids (20–25) in excellent yields. These selenoalkanoates (8–13) and selenoalkanoic acids (20–25) have been characterized by elemental analysis and various spectroscopic techniques

  一些新颖的和合成地重要吡啶基/萘/（二苯基）甲硒的取代的链烷酸（20 - 25），使用一种高效且操作简单的策略已被合成。起始衬底，乙基吡啶基/萘/（二苯基）甲硒基取代的链烷酸酯（8 - 13）很容易被治疗乙基chloroalkanoates的制备7（一- ç）与亲核硒试剂RSeNa +，从联吡啶/二萘/二裂解产生（二苯甲基）二硒化物（1 – 6）与硼氢化钠的乙醇溶液。乙基吡啶/萘/（二苯基）甲硒基取代的链烷酸酯（8 - 13）上基本水解和随后酸化得到吡啶基/萘/（二苯基）甲硒基取代的链烷酸（20 - 25）以优良产率。这些硒代链烷酸酯（8 – 13）和硒代链烷酸（20 – 25）已经通过元素分析和各种光谱技术进行了表征。NMR（1 H，13 C和77 Se），IR和质谱。2-吡啶基硒酸乙烯酸（20a的分子结构），还借助单晶X射线分析建立了2-萘基硒代乙酸（23a）和2-（二苯基）甲基硒代乙酸（24a）。
• Facile one pot synthesis of highly photoresponsive coinage metal selenides (Cu_1.8Se and Ag₂Se) achieved through novel Cu and Ag pyridylselenolates as molecular precursors
  作者：Gourab Karmakar、Adish Tyagi、Alpa Y. Shah、Sandeep Nigam、A. P. Wadawale、G. Kedarnath、Bal Govind Vats、N. Naveen Kumar、Vishal Singh

  DOI：10.1039/d2dt01897g

  日期：——

  morphology, elemental composition and band gap of these nanocrystals were determined from pXRD, electron microscopy (SEM and TEM), EDS and DRS-UV, respectively. The band gap of these nanocrystals lies in the range suitable for solar cell applications. Finally, these nanocrystal-based prototype photo-electrochemical cells exhibit high photoresponsivity and stability under alternating light and dark conditions

  硒化铜 (Cu 1.8 Se) 和硒化银 (Ag 2 Se) 作为具有成本效益和可持续发展的太阳能电池的高效吸收材料，受到了前所未有的关注。非常需要在纳米范围内对这些奇异材料进行相纯制备。该帐户概述了使用新型配合物 [Cu2-SeC 5 H 2 ( Me-4,6) 2 N}] 4 ( 1 ), [ Ag 2 -Sec 5 H 2 (Me-4,6) 2 N}] 6 ( 2 ) 和 [Ag2-SeC 5 H3 (Me-5)N}] 6 ·2C 6 H 5 CH 3 ( 3 ·2C 6 H 5 CH 3 ) 作为单源分子前体 (SSP)。结构研究表明，Cu 和 Ag 配合物分别结晶成四聚体和六聚体形式。这种在配合物中观察到的结构多样性已通过DFT 计算合理化，并归因于金属-金属键背书的能量学。配合物1在油胺中相对较低的温度下热解得到立方白锆石 Cu 1.8 Se 和配合物2和3制备了斜方晶系瑙曼石Ag