bis(phenylseleno)methane | 20343-90-2

• 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: bis(phenylseleno)methane
• 英文别名: Bis(phenylseleno)methan；bis(phenylselanyl)methane；1,1-bis(phenylseleno)methane；1,1'-(methylenediselanyl)dibenzene；Benzene, 1,1'-[methylenebis(seleno)]bis-；phenylselanylmethylselanylbenzene
• CAS: 20343-90-2
• 化学式: C₁₃H₁₂Se₂
• 分子量: 326.158
• InChiKey: JMHGZOLIVCLHEK-UHFFFAOYSA-N

物化性质

• 熔点：
  30-31 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  138 °C(Press: 0.1 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  1.42
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  bis(phenylseleno)methane 生成 二苄基甲酮
  参考文献：
  名称：

  Uemura, Sakae; Ohe, Kouichi; Sugita, Nobuyuki, Journal of the Chemical Society. Perkin transactions I, 1990, # 6, p. 1697 - 1703

  摘要：

  DOI：
• 作为产物：
  描述：

  氯甲基苯基硒化物 在 aluminum oxide 作用下， 反应 0.5h， 以87%的产率得到bis(phenylseleno)methane
  参考文献：
  名称：

  A Convenient Synthesis of Arylselenoacetals and α-Halo-α-(phenylseleno)alkanes

  摘要：

  alpha-Halo-alpha-(phenylseleno)alkanes are prepared by treatment of selenoacetals with halogenating agents. Selenoacetals are produced by heating alpha-halo-alpha-(phenylseleno)alkanes on neutral alumina

  DOI：

  10.1080/00397919508010797

文献信息

• Rhodium-Catalyzed Reductive Coupling of Disulfides and Diselenides with Alkyl Halides, Using Hydrogen as a Reducing Agent
  作者：Kaori Ajiki、Masao Hirano、Ken Tanaka

  DOI：10.1021/ol051588n

  日期：2005.9.1

  [reaction: see text] We have established that RhCl(PPh3)3 catalyzes a reductive coupling of disulfides and diselenides with alkyl halides in the presence of triethylamine using hydrogen as a reducing agent. This reaction serves as a convenient new method to produce unsymmetrical sulfides and selenides from disulfides and diselenides instead of unstable and odoriferous thiols and selenols.

  [反应：见正文]我们已经确定，RhCl（PPh3）3在三乙胺存在下使用氢作为还原剂催化二硫化物和二硒化物与烷基卤化物的还原偶联。该反应用作从二硫化物和二硒化物而不是不稳定的和有气味的硫醇和硒醇生产不对称硫化物和硒化物的便捷新方法。
• Synthesis of 1,1-Dibromo-3-hydroxyalkanes via Opening of Cyclic Sulfates
  作者：Hans Christian Stiasny

  DOI：10.1055/s-1996-4193

  日期：1996.2

  3-Alkoxy-1,1-dibromoalkanes are interesting substrates for diastereoselective bromine/lithium exchange reactions. A general route to the precursor 1,1-dibromo-3-hydroxyalkanes is described here via reaction of dibromomethyllithium with cyclic sulfates of 1,2-diols.

  3-烷氧基-1,1-二溴烷是用于二氨基酸选择性溴锂交换反应的有趣底物。本文通过二溴甲基锂与1,2-二醇的环硫酸酯反应，描述了一种制备前体1,1-二溴-3-羟基烷的通用路线。
• The reaction of selenenyl halides with wittig reagents
  作者：N. Petragnani、R. Rodrigues、J.V. Comasseto

  DOI：10.1016/s0022-328x(00)87285-x

  日期：1976.7

  The transylidation reactions of PhSeBr with two equivalents of an alkylidene-triphenylphosphorane give selenophosphoranes, Ph3PCRSePh. These also can be obtained by treating the corresponding selenophosphonium salts, prepared by quarternization of triphenylphosphine with PhSeCHRBr, with n-BuLi. The selenophosphoranes react with aldehydes in situ (Wittig reaction) to give the expected vinylic selenides

  PhSeBr的与两个当量的transylidation反应亚烷基-三苯基正膦给予selenophosphoranes中，Ph 3 PCRSePh。这些也可以通过处理相应的selenophosphonium盐而获得，制备三苯膦quarternization与PhSeCHRBr，用n-BuLi。所述selenophosphoranes与醛反应，原位（Wittig反应），得到在良好的产率的预期乙烯基硒化物。讨论了反应的立体化学。
• Regioselective transition metal- and halogen-free direct dithiolation at C(sp³)–H of nitrotoluenes with diaryl disulfides
  作者：Shailesh Kumar、Rahul Kadu、Sangit Kumar

  DOI：10.1039/c6ob01856d

  日期：——

  tert-butoxide-mediated regioselective direct C–S bond formation at the C(sp3)–H position of nitrotoluenes with disulfides in DMSO at room temperature. The developed reaction generated, in good yields, various dithioacetals having OMe, halogen, and NH2 functionalities at various positions of the arene rings of the disulfides. Interestingly, in the absence of nitrotoluene, diaryl disulfides and diselenides underwent one-carbon

  在这里，我们描述了室温下在DMSO中硝基甲苯与二硫键的C（sp 3）–H位置形成叔丁醇钾介导的区域选择性直接C–S键的形成。进行的反应以高收率产生了在二硫化物的芳环的各个位置具有OMe，卤素和NH 2官能度的各种二硫缩醛。有趣的是，在不存在硝基甲苯的情况下，对二芳基二硫化物和二硒化物进行一碳同系形成二硫缩醛和二硒缩醛。将合成的二硫缩醛转化为4-硝基苯甲醛和7-（双（苯硫基）甲基）-1 H-吲哚。
• Regioselective Synthesis of Selenide Ethers through a Decarboxylative Coupling Reaction
  作者：Fei-Hu Cui、Jing Chen、Shi-Xia Su、Yan-li Xu、Heng-shan Wang、Ying-ming Pan

  DOI：10.1002/adsc.201700676

  日期：2017.11.23

  An efficient and selective approach to the synthesis of selenide ethers containing one or two geminal C–Se bonds from readily available diselenides and phenylacetic acids was developed. Compounds containing one C–Se bond were prepared by employing air as the oxidant under metal-free conditions, whereas compounds having two geminal C–Se bonds were formed via the iron(III) chloride/oxygen/cesium carbonate

  已开发出一种有效的，选择性的方法，可以从容易获得的二硒化物和苯乙酸合成含一个或两个双键C-Se键的硒醚。通过在无金属条件下将空气用作氧化剂来制备包含一个C-Se键的化合物，而通过氯化铁（III）/氧/碳酸铯（FeCl 3 / O 2）形成具有两个双键C-Se键的化合物。/ Cs 2 CO 3）系统。此外，在标准反应条件下，1,2-二苯基二硫烷也可以平稳地转化为相应的硫醚产物。