tert-butyl phenyl selenide | 22233-90-5

• 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: tert-butyl phenyl selenide
• 英文别名: Phenyl-tert.-butylselenid；t-butyl phenyl selenide；tert-butyl(phenyl)selane；Benzene, [(1,1-dimethylethyl)seleno]-；tert-butylselanylbenzene
• CAS: 22233-90-5
• 化学式: C₁₀H₁₄Se
• 分子量: 213.181
• InChiKey: BHLYTKXNEOBHAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  tert-butyl phenyl selenide 在 sodium perchlorate 作用下， 以 乙腈 为溶剂， 以95%的产率得到二苯硒醚
  参考文献：
  名称：

  Latypova, V. Z.; Zhuikov, V. V.; Kargin, Yu. M., Journal of general chemistry of the USSR, 1986, vol. 56, p. 723 - 727

  摘要：

  DOI：
• 作为产物：
  描述：

  O-(tert-butyl) Se-phenyl selenocarbonate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 tert-butyl phenyl selenide
  参考文献：
  名称：

  O-(tert-butyl) Se-phenyl selenocarbonate: A convenient, bench-stable and metal-free precursor of benzeneselenol

  摘要：

  A study by our laboratory shows that air, light and moisture stable O-(tert-butyl) Se-phenyl selenocarbonate could be employed as a safer, practical and efficient alternative to generate "in situ" benzeneselenol or benzeneselenolate anion under different and transition metal-free conditions. This procedure seems to be of general application since the nucleophilic selenium species obtained can be trapped by electrophiles such as alkyl halides, epoxides and electron-deficient alkenes and alkynes under different reaction conditions. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2020.131311

文献信息

• On the reactivity of indium(III) benzenechalcogenolates (chalcogen = sulfur and selenium) towards organyl halides for the synthesis of organyl phenyl chalcogenides
  作者：Clovis Peppe、Liérson Borges de Castro

  DOI：10.1139/v09-043

  日期：2009.5

  was examined. A practical one-pot method to prepare organyl phenyl chalcogenides from indium metal and diphenyl dichalcogenide was found. The coupling is fairly broad in scope and generally works better for organyl halides capable to produce stable carbocations.

  检测了铟 (III) 苯硫属元素化物（硫属元素 = 硫、硒）对有机卤化物（有机基 = 烷基、烯丙基、苄基、酰基）的反应性。发现了一种从铟金属和二苯基二硫属元素化物制备有机苯基硫属元素化物的实用一锅法。偶联的范围相当广泛，通常对能够产生稳定碳正离子的有机卤化物效果更好。
• Indium(I) Iodide-Mediated Cleavage of Diphenyl Diselenide. An Efficient One-Pot Procedure for the Synthesis of Unsymmetrical Diorganyl Selenides
  作者：Brindaban C. Ranu、Tanmay Mandal、Sampak Samanta

  DOI：10.1021/ol034178c

  日期：2003.5.1

  A simple and efficient procedure has been developed for the synthesis of unsymmetrical diorganyl selenides through a one-pot indium(I) iodide-mediated reaction of alkyl halide and diphenyl diselenide in methylene chloride at room temperature. [reaction: see text]

  通过在室温下通过一锅碘化铟（I）碘化物介导的烷基卤与二苯二硒化物在二氯甲烷中的反应，已开发出一种简单有效的方法来合成不对称的二有机基硒化物。[反应：看文字]
• Indium(I) Iodide-Promoted Cleavage of Diaryl Diselenides and Disulfides and Subsequent Condensation with Alkyl or Acyl Halides. One-Pot Efficient Synthesis of Diorganyl Selenides, Sulfides, Selenoesters, and Thioesters
  作者：Brindaban C. Ranu、Tanmay Mandal

  DOI：10.1021/jo0493727

  日期：2004.8.1

  disulfides undergo facile cleavages by indium(I) iodide and the corresponding generated selenate and thiolate anions condense in situ with alkyl or acyl halides present in the reaction mixture. Thus, a simple, efficient, and general procedure has been developed for the synthesis of unsymmetrical diorganyl selenides, sulfides (thioethers), selenoesters, and thioesters by this one-pot reaction at room temperature

  二苯基二硒化物和二硫化物容易被碘化铟裂解，相应生成的硒酸根和硫醇根阴离子与反应混合物中存在的烷基或酰基卤原位缩合。因此，已经开发出一种简单，有效且通用的方法，用于通过室温下的这一一锅法反应合成不对称的二有机基硒化物，硫化物（硫醚），硒酸酯和硫代酯。
• General synthesis of alkyl phenyl selenides from organic halides mediated by zinc in aqueous medium
  作者：Lothar W Bieber、Ana C.P.F de Sá、Paulo H Menezes、Simone M.C Gonçalves

  DOI：10.1016/s0040-4039(01)00820-6

  日期：2001.7

  halides of different structural types react with diphenyl diselenide and zinc dust in aqueous medium to give alkyl phenyl selenides. Benzylic and allylic bromides, α-bromoesters, acids and ketones and some primary alkyl iodides produce high yields even under acidic conditions. Less reactive halides need basic medium. The reaction proceeds equally well in the presence of various unprotected functional

  不同结构类型的有机卤化物与二苯基二硒化物和锌粉在水性介质中反应，生成烷基苯基硒化物。苄基和烯丙基溴化物，α-溴代酸酯，酸和酮以及某些伯烷基碘化物即使在酸性条件下也能产生高收率。反应性较低的卤化物需要基本介质。在各种未保护的官能团的存在下，反应同样良好地进行。对照实验通过烷基支持S H 2机理。
• Factors Controlling Photochemical Cleavage of the Energetically Unfavorable Ph−Se Bond of Alkyl Phenyl Selenides
  作者：Akihiko Ouchi、Suyou Liu、Zhong Li、S. Ajaya Kumar、Toshiaki Suzuki、Takeshi Hyugano、Haruo Kitahara

  DOI：10.1021/jo701447a

  日期：2007.11.1

  unexpected amount of Ph−Se bond cleavage (35% in n-hexane at 248 nm) during photolysis. Solvent viscosity, wavelength of light, and the structure of alkyl substituents were the major factors that controlled Ph−Se bond cleavage. The ratio of Ph−Se bond cleavage decreased with increasing solvent viscosity and laser wavelength. The effect of alkyl substituents on the ratio of bond cleavages, Ph−Se/total C−Se

  研究了烷基苯基硒化物（1）的主要光化学路径，并阐明了由苯基硒化物的光解引起的碳自由基反应获得的产品的化学收率存在较大偏差的原因。的KrF准分子激光photolyses ñ -戊基苯基硒化物（1A），得到1-戊烯（2A），Ñ戊烷（图3a），ñ -癸烷（4A），二戊硒化物（图5a），苯（6），二戊硒（7a中）和主要的光产物二苯二硒化物（7），以及化合物2a，3a，图4a，图5a和7由戊基-硒键断裂，并形成图5a，6，和图7a通过PH-Se键裂解。光产物的选择性表明发生了意外数量的Ph-Se键裂解（n中35％-在248 nm的正己烷中进行光解。溶剂粘度，光波长和烷基取代基的结构是控制Ph-Se键断裂的主要因素。Ph-Se键断裂的比例随溶剂粘度和激光波长的增加而降低。对于五个烷基苯基硒化物，研究了烷基取代基对键裂解率Ph-Se /总C-Se的影响。该比例以戊基> 2-甲基烯丙基>烯丙基> 1-乙基

表征谱图