二硒化,二-1-萘基 | 1787-80-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 二硒化,二-1-萘基
• 英文名称: 2-bis[3,5bis(trifluoromethyl)phenyl]diselane
• 英文别名: 1,2-di(naphthalen-1-yl)diselane；di(1-naphthyl) diselenide；1,1'-dinaphthyl diselenide；bis(1-naphthyl) diselenide；dinaphthyl diselenide；1,2-di(naphthalen-2-yl)diselane；Diselenide, di-1-naphthalenyl；1-(naphthalen-1-yldiselanyl)naphthalene
• CAS: 1787-80-0
• 化学式: C₂₀H₁₄Se₂
• 分子量: 412.251
• InChiKey: XFUCRHYSJRXATP-UHFFFAOYSA-N

物化性质

• 熔点：
  87-88 °C
• 沸点：
  552.9±33.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  二硒化,二-1-萘基 以 四氢呋喃 为溶剂， 生成 1-naphthylseleno radical
  参考文献：
  名称：

  Laser-flash photolysis of naphthyl diselenides; reactivities of naphthylseleno radicals

  摘要：

  Transient absorption spectra of 1-naphthylseleno (1-NaphSe(.)), and 2-naphthylseleno (2-NaphSe(.)) radicals, which are generated by laser-flash photolysis of the corresponding diselenides, were observed. The reactions of 1-NaphSe(.), and 2-NaphSe(.) with 2-methyl-1,3-butadiene and alpha-methylstyrene were investigated by following the decay rates of these seleno radicals. By both steady-state and laser-flash photolysis, it is proved that these seleno radicals add to alkenes in a reversible manner. The reaction rate constants for such reversible addition reactions were determined by conducting the reaction in the presence of O(2), which traps selectively the carbon-centered radicals formed by the addition reaction of the seleno radicals to the alkenes. The reactivity of 2-NaphSe(.) is higher than that of 1-NaphSe(.), both of which are less reactive than PhSe .. These reactivities were interpreted with the properties of SOMO calculated by MO method. (C) 1998 John Wiley & Sons, Inc.

  DOI：

  10.1002/(sici)1097-4601(1998)30:3<193::aid-kin4>3.0.co;2-n
• 作为产物：
  描述：

  1-碘萘 在 selenium 、 potassium hydroxide 作用下， 以 水 为溶剂， 反应 4.5h， 以97%的产率得到二硒化,二-1-萘基
  参考文献：
  名称：

  The direct synthesis of symmetrical disulfides and diselenides by metal–organic framework MOF-199 as an efficient heterogenous catalyst

  摘要：

  MOF-199被用作高效的杂化催化剂，用于在聚乙二醇（PEG）中从芳基卤化物和元素S/Se一锅法合成有机二硫化物/二硒化物，产率良好至优异。

  DOI：

  10.1039/c5ra16879a

文献信息

• Nucleophilic cleavage of lactones and esters with zinc selenolates prepared from diselenides in the presence of Zn/AlCl3
  作者：Mohammad Nazari、Barahman Movassagh

  DOI：10.1016/j.tetlet.2008.11.036

  日期：2009.1

  The utility of zinc selenolates for effecting nucleophilic cleavage of simple lactones and esters has been investigated. When zinc selenolate generated via Zn/AlCl3-promoted cleavage of diselenides was reacted with simple lactones and esters, efficient nucleophilic alkyl–oxygen bond cleavage proceeded generating the corresponding carboxylic acids in moderate to excellent yields.

  已经研究了硒酸锌用于简单内酯和酯的亲核裂解的用途。当通过Zn / AlCl 3促进的二硒化物裂解生成的硒化锌与简单的内酯和酯反应时，有效的亲核烷基-氧键裂解便开始进行，从而以中等至极好的收率生成了相应的羧酸。
• Atom-economical selenation of electron-rich arenes and phosphonates with molecular oxygen at room temperature
  作者：Samir Kumar Bhunia、Pritha Das、Ranjan Jana

  DOI：10.1039/c8ob02792g

  日期：——

  An environmentally benign selenation of electron-rich arenes and phosphonates is developed adopting a novel recycle–reuse–reduce strategy for selenol by oxygen.

  一种采用新颖的循环-重复利用-减少策略，通过氧气对富电子芳烃和膦酸酯进行环保的硒化反应被开发出来。
• Regioselective, Solvent- and Metal-Free Chalcogenation of Imidazo[1,2-<i>a</i> ]pyridines by Employing I₂ /DMSO as the Catalytic Oxidation System
  作者：Jamal Rafique、Sumbal Saba、Alisson R. Rosário、Antonio L. Braga

  DOI：10.1002/chem.201600800

  日期：2016.8.8

  molecular‐iodine‐catalyzed chalcogenations (S and Se) of imidazo[1,2‐a]pyridines were achieved by using diorganoyl dichalcogenides under solvent‐free conditions. This approach afforded the desired products that had been chalcogenated regioselectively at the C3 position in up to 96 % yield by using DMSO as an oxidant, in the absence of a metal catalyst, and under an inert atmosphere. This mild, green approach allowed

  通过在无溶剂条件下使用二有机基二卤化氢实现咪唑并[1,2- a ]吡啶的高效分子碘催化硫属元素化（S和Se）。通过使用DMSO作为氧化剂，在没有金属催化剂的情况下，并且在惰性气氛下，该方法提供了所需的产物，该产物已经在C3位置进行了区域硫磺化，产率高达96％。这种温和的绿色方法可以制备具有结构多样性的不同类型的硫族化咪唑并[1,2- a ]吡啶。此外，当前协议还扩展到其他N杂环核。
• Visible-light-induced metal and reagent-free oxidative coupling of <i>sp</i>² C–H bonds with organo-dichalcogenides: synthesis of 3-organochalcogenyl indoles
  作者：Vandana Rathore、Sangit Kumar

  DOI：10.1039/c9gc00007k

  日期：——

  and halo either on indoles or aryl dichalcogenides showed amenability to the developed reaction. Furthermore, thiocyanation of the sp2 C–H bonds of indoles has been accomplished by this visible light induced method. A mechanistic understanding by UV-visible, EPR spectroscopy, and cyclic voltammetry suggests that light induces electron transfer from the electron rich arene to oxygen providing an arene

  在这里，已经提出了一种独特的可见光诱导方法，用于将吲哚和苯胺的sp 2 C–H键进行有机硫属化，使用二芳基二卤化碳（S，Se和Te）和氧气作为氧化剂，避免了光催化剂，碱，室温下，在丙酮中加入催化剂和试剂。这种良性方案允许以良好或优异的产率获得各种3-芳基硒基吲哚，3-芳基硫代吲哚，甚至3-芳基碲代吲哚。吲哚或芳基二卤化物上的各种官能团，即甲氧基和卤素，都显示出对已开发的反应的适应性。此外，sp 2的硫氰化吲哚的CH键已通过这种可见光诱导方法完成。通过紫外可见光，EPR光谱和循环伏安法进行的机理理解表明，光诱导电子从富电子的芳烃向氧的转移，从而提供芳烃自由基阳离子和超氧自由基阴离子。随后，自由基阳离子与芳基二硫代氰化物的反应提供了二芳基硫属取代基阳离子，其在去除质子后得到不对称的3-吲哚基芳基硫属化物。
• Direct, Metal-free C(sp² )−H Chalcogenation of Indoles and Imidazopyridines with Dichalcogenides Catalysed by KIO₃
  作者：Jamal Rafique、Sumbal Saba、Marcelo S. Franco、Luana Bettanin、Alex R. Schneider、Lais T. Silva、Antonio L. Braga

  DOI：10.1002/chem.201705404

  日期：2018.3.15

  synthesis of 3‐Se/S‐indoles and imidazo[1,2‐a]pyridines through direct C(sp2)−H bond chalcogenation of heteroarenes with half molar equivalents of different dichalcogenides, using KIO3 as a non‐toxic, easy‐to‐handle catalyst and a stoichiometric amount of glycerol. The reaction features are high yields, based on atom economy, easy performance on gram‐scale, metal‐ and solvent‐free conditions as well as applicability

  本文中，我们报告了一种更环保的协议，该方法通过杂芳烃的直接C（sp 2）-H键硫代半数当量的不同二硫代半乳糖苷合成3-Se / S-吲哚和咪唑并[1,2- a ]吡啶KIO 3是一种无毒，易于操作的催化剂和化学计量的甘油。该反应的特征是基于原子经济性的高收率，在克级，无金属和无溶剂条件下易于操作以及适用于不同类型的N-杂芳烃。

表征谱图