(Z)-1,2-Bis(phenylseleno)-1-hexene | 101349-67-1

• 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: (Z)-1,2-Bis(phenylseleno)-1-hexene
• 英文别名: 1,2-bis(phenylselanyl)hex-1-ene；1,1'-[(1Z)-hex-1-ene-1,2-diylbis(seleno)]dibenzene；(Z)-1,2-bis(phenylseleno)hex-1-ene；[(Z)-1-phenylselanylhex-1-en-2-yl]selanylbenzene
• CAS: 101349-67-1
• 化学式: C₁₈H₂₀Se₂
• 分子量: 394.277
• InChiKey: FRCNENQWGRMFOZ-SDXDJHTJSA-N

物化性质

• 沸点：
  430.8±41.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.08
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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：

  二苯基二硒醚 、 1-己炔 在 KF/Al₂O₃ 作用下， 反应 6.0h， 以32%的产率得到(Z)-1,2-Bis(phenylseleno)-1-hexene
  参考文献：
  名称：

  使用KF / Al 2 O 3从炔烃中简单，立体选择性地合成（Z）-1,2-双芳基戊基戊烯基烯烃

  摘要：

  通过二芳基二硒化物与末端炔烃的一锅反应来合成标题化合物，从而避免了之前制备芳基硒基炔烃的情况。反应在温和条件下，使用KF / Al 2 O 3和PEG-400作为溶剂，在一定范围的末端炔烃下进行。立体选择性地将二芳基二硒化物加成至炔烃中，以良好的收率仅得到（Z）-1,2-双-芳基-杂戊基烯基烯烃。使用微波辐射将反应时间缩短至几分钟，并且KF / Al 2 O 3 / PEG-400系统可以重复使用一次，而无需事先进行类似活性的处理。

  DOI：

  10.1016/j.tet.2012.08.055

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。
• A Recyclable Biphasic System for Stereoselective and Easily Handled Hydrochalcogenations
  作者：Caterina Tidei、Luca Sancineto、Luana Bagnoli、Benedetta Battistelli、Francesca Marini、Claudio Santi

  DOI：10.1002/ejoc.201402668

  日期：2014.9

  Vinyl selenides and vinyl sulfides were prepared by hydrochalcogenation of alkynes with selenols and thiols generated in situ by the reduction of the corresponding diselenides and disulfides with elemental zinc in a biphasic acidic medium. The yields, stereoselectivity as well as the possibility of reusing the aqueous medium up to ten times are discussed.

  通过在双相酸性介质中用元素锌还原相应的二硒化物和二硫化物而原位生成的硒醇和硫醇，通过炔烃与硒醇和硫醇的氢化硫属化反应制备乙烯基硒化物和乙烯基硫化物。讨论了产率、立体选择性以及将水性介质重复使用多达十次的可能性。
• ——
  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.
• Photo-initiated addition of diphenyl diselenide to acetylenes
  作者：Akiya Ogawa、Hiroshi Yokoyama、Kazuyuki Yokoyama、Teruyuki Masawaki、Nobuaki Kambe、Noboru Sonoda

  DOI：10.1021/jo00019a052

  日期：1991.9
• Highly stereoselective method to prepare bis-phenylchalcogen alkenes via addition of chalcogenolate to phenylseleno alkynes
  作者：Gelson Perin、Elton L. Borges、Diego Alves

  DOI：10.1016/j.tetlet.2012.02.028

  日期：2012.4

  The preparation of bis-phenylchalcogen alkenes starting from phenylseleno alkynes is described. The nucleophilic species of selenium, tellurium and sulfur were generated in situ from the reaction of the respective diphenyl dichalcogenide with NaBH4 in PEG-400 as solvent. The chalcogenolate anions were efficiently and selectively added to a variety of phenylselenoalkynes at mild conditions, furnishing the respective (Z)-1,2-bis-phenylchalcogen alkenes in good yields. (C) 2012 Elsevier Ltd. All rights reserved.