phenyl(1-phenylvinyl)selenide | 61634-68-2

• 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: phenyl(1-phenylvinyl)selenide
• 英文别名: 1-Phenylseleno-1-phenylethen；Benzene, [(1-phenylethenyl)seleno]-；1-phenylethenylselanylbenzene
• CAS: 61634-68-2
• 化学式: C₁₄H₁₂Se
• 分子量: 259.209
• InChiKey: LNVYZKXVIFOQNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  355.6±25.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• 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

• 作为产物：
  描述：

  benzyl phenyl selenide 在 间氯过氧苯甲酸 作用下， 生成 phenyl(1-phenylvinyl)selenide
  参考文献：
  名称：

  Selenium stabilized anions. Selenoxide syn elimination and sila-Pummerer rearrangement of .alpha.-silyl selenoxides

  摘要：

  DOI：

  10.1021/jo00430a021

文献信息

• Palladium and platinum catalyzed hydroselenation of alkynes: SeH vs SeSe addition to CC bond
  作者：Valentine P Ananikov、Denis A Malyshev、Irina P Beletskaya、Grigory G Aleksandrov、Igor L Eremenko

  DOI：10.1016/s0022-328x(03)00546-1

  日期：2003.8

  alkynes catalyzed by Pd(PPh3)4 and Pt(PPh3)4 has shown that the palladium complex gives products of both SeH and SeSe bond addition to the triple bond of alkynes, while the platinum complex selectively catalyzes SeH bond addition. The key intermediate of PhSeH addition to the metal center, namely Pt(H)(SePh)(PPh3)2, was detected by 1H-NMR spectroscopy. The analogous palladium complex rapidly decomposes

  对Pd（PPh 3）4和Pt（PPh 3）4催化的炔烃加氢精制的机理研究表明，钯配合物使SeH和SeSe键的产物加成到炔烃的三键上，而铂络合物选择性催化SeH键的添加。通过1 H-NMR光谱检测到PhSeH添加到金属中心的关键中间体，即Pt（H）（SePh）（PPh 3）2。类似的钯配合物随着分子氢的释放而迅速分解。开发了一种方便的方法来制备马尔可夫尼可夫盐精制产物H 2CC（SePh）R，并研究了该反应的范围。的马氏产物H的第一X射线结构2 CC（SEPH）CH 2 Ñ + HME 2 ·HOOCCOO -报道。
• The first example of transition-metal-catalyzed hydroselenation of acetylenes
  作者：Hitoshi Kuniyasu、Akiya Ogawa、Ken-Ichiro Sato、Ilhyong Ryu、Noboru Sonoda

  DOI：10.1016/s0040-4039(00)61136-x

  日期：1992.9

  A variety of transition metal complexes catalyzed the regioselective hydroselenation of acetylenes. In particular, the palladium acetate-catalyzed reaction afforded the Markovnikov adducts with high selectivity.

  多种过渡金属络合物催化乙炔的区域选择性加氢硒化。特别地，乙酸钯催化的反应提供了具有高选择性的马尔可夫尼可夫加合物。
• Palladium(0)-catalyzed regio- and stereoselective addition of heteroatom compounds bearing Si–Se, Ge–Se, and Si–Ge bonds to phenylacetylene
  作者：Akiya Ogawa、Hitoshi Kuniyasu、Mitsuhiro Takeba、Takuma Ikeda、Noboru Sonoda、Toshikazu Hirao

  DOI：10.1016/s0022-328x(97)00514-7

  日期：1998.8

  A novel palladium(0)-catalyzed addition of a silyl selenide (1, Me3SiSePh) to phenylacetylene proceeds regio- and stereoselectively to give (Z)-1-phenylseleno-2(trimethylsilyl)styrene (2). Similarly, a germyl selenide (3, Me3GeSePh) adds to phenylacetylene with excellent regio- and stereoselectivity.

  新颖的钯（0）催化的硒化甲硅烷基（1，Me 3 SiSePh）加到苯乙炔中的区域和立体选择性生成（Z）-1-苯基硒基2（三甲基甲硅烷基）苯乙烯（2）。同样，胚芽硒化物（3，Me 3 GeSePh）以优异的区域选择性和立体选择性加到苯乙炔中。
• A simple and general preparation of vinylic sulfides, selenides and tellurides
  作者：Claudio C. Silveira、Paulo Cesar S. Santos、Samuel R. Mendes、Antonio L. Braga

  DOI：10.1016/j.jorganchem.2008.09.039

  日期：2008.12

  A general method for the synthesis of vinylic chalcogenides by nucleophilic and Ni-catalyzed vinylic substitution on vinylic halides by phenyl chalcogenolates is described. The reactions were regio and stereoselective for the nickel catalyzed substitution, and mixture of isomers was observed for some examples in the thermal process in DMF.

  描述了通过苯基硫属元素化物在乙烯基卤化物上通过亲核和Ni催化的乙烯基取代来合成乙烯基硫属元素化物的一般方法。对于镍催化的取代，该反应是区域性和立体选择性的，并且在DMF的热过程中的一些实例中观察到异构体的混合物。
• ——
  作者：V. P. Ananikov、D. A. Malyshev、I. P. Beletskaya

  DOI：10.1023/a:1022500420741

  日期：——

  Addition of benzeneselenol to terminal alkynes HCdropCR, catalyzed by Pd(0) complexes, leads to formation of mixtures of mono- and bis(phenylseleno)alkenes, depending on the nature of the R substituent. Electron-donor groups (R = Bu, CH2OH, CH2NMe2) give rise to addition according to the Markownikoff rule, whereas from alkynes with electron-acceptor groups (R = Ph, COOMe) mixtures of products are formed as a result of side reactions. A probable reaction mechanism includes oxidative addition of benzeneselenol to the metal, alkyne insertion into the Pd-Se bond, and reductive elimination.