(2-butylselanyl-vinyl)-benzene | 105821-97-4

• 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: (2-butylselanyl-vinyl)-benzene
• 英文别名: (Z)-1-butylseleno-2-phenylethene；(Z)-butyl(styryl)selane；[(Z)-2-butylselanylethenyl]benzene
• CAS: 105821-97-4
• 化学式: C₁₂H₁₆Se
• 分子量: 239.219
• InChiKey: HGDMWYQWWBKKMK-LUAWRHEFSA-N

物化性质

• 沸点：
  307.9±25.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (2-butylselanyl-vinyl)-benzene 、 chlorozinc(1+),methoxybenzene 在 四(三苯基膦)钯 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以58%的产率得到苯,1-甲氧基-4-[(1Z)-2-苯基乙烯基]-
  参考文献：
  名称：

  硒化钠与有机卤化物和炔烃反应的立体选择性合成Z-乙烯基硒化物

  摘要：

  通过亚硒酸钠与有机卤化物的反应，然后添加炔烃的立体选择性合成Z-乙烯基硒化物的方法得以开发。

  DOI：

  10.1002/ejoc.201900544
• 作为产物：
  描述：

  苯,[(丁基硒代)乙炔基]- 在 Schwartz's reagent 、 水 作用下， 生成 (2-butylselanyl-vinyl)-benzene
  参考文献：
  名称：

  Hydrozirconation of acetylenic chalcogenides. Synthesis and reactions of zirconated vinyl chalcogenide intermediates

  摘要：

  Acetylenic tellurides react with Cp2Zr(H)Cl in THF at room temperature to give the alpha-zirconated vinyl telluride intermediates 39, which react with a wide range of electrophiles to give several types of trisubstituted olefins, such as alpha-halo vinyl tellurides, ketene telluro(seleno) acetals, ketene telluro acetals, and vinylic tellurides of Z configuration. Acetylenic selenides undergo similar reactions, but a lack of regioselectivity results in the formation of a mixture of alpha-zirconated 19 and beta- zirconated 20 vinylic selenide intermediates. After a derailed study was established that the use of 2.0 equivalents of Cp2Zr(H)Cl is crucial to perform the total hydrozirconation of acetylenic selenides or tellurides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00014-3

文献信息

• Hydroselenation of Alkynes by Lithium Butylselenolate:  An Approach in the Synthesis of Vinylic Selenides
  作者：Gilson Zeni、Marcelo P. Stracke、Cristina W. Nogueira、Antonio L. Braga、Paulo H. Menezes、Helio A. Stefani

  DOI：10.1021/ol0498904

  日期：2004.4.1

  Vinylic selenides were prepared in good yields by hydroselenation of alkynes with lithium butylselenolate generated by reaction of n-butyllithium with elemental selenium. The regio- and stereochemistry of the hydroselenation depend on the nature of the substituents bonded to the alkyne.

  通过炔烃与正丁基锂与元素硒反应生成的丁基硒化锂进行氢硒化，可以制备高产率的乙烯基硒化物。加氢硒化的区域化学和立体化学取决于与炔烃键合的取代基的性质。
• Application of organoselenides in the Suzuki, Negishi, Sonogashira and Kumada cross-coupling reactions
  作者：A. L. Stein、F. N. Bilheri、G. Zeni

  DOI：10.1039/c5cc06347g

  日期：——

  A powerful tool for constructing new carbon–carbon bonds via palladium-catalyzed cross-coupling reactions of unsaturated organoselenides is described.

  通过钯催化的不饱和有机硒化合物交叉偶联反应，构建新的碳-碳键的强大工具被描述。
• Amosova, S. V.; Potapov, V. A.; Kashik, A. S., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 3.1, p. 470 - 475
  作者：Amosova, S. V.、Potapov, V. A.、Kashik, A. S.、Gusarova, N. K.、Sinegovskaya, L. M.、et al.

  DOI：——

  日期：——
• Potapov, Vladimir A.; Amosova, Svetlana V., Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 79, # 1.4, p. 277 - 280
  作者：Potapov, Vladimir A.、Amosova, Svetlana V.

  DOI：——

  日期：——
• DES as a green solvent to prepare 1,2-bis-organylseleno alkenes. Scope and limitations
  作者：Eric F. Lopes、Lóren C. Gonçalves、Julio C.G. Vinueza、Raquel G. Jacob、Gelson Perin、Claudio Santi、Eder J. Lenardão

  DOI：10.1016/j.tetlet.2015.10.095

  日期：2015.12

  We describe here our results on the use of choline chloride/urea 1:2 as a deep eutectic solvent (DES) in the synthesis of vinyl selenides. A good selectivity for the (E)-1,2-bis-organylseleno alkenes was observed starting from terminal alkynes and diaryl or dibutyl diselenides in the presence of NaBH4. The reaction of 1,3-butadiynes with diphenyl diselenide afforded exclusively the respective mono-selenylated (Z)-alkenynes. Diphenyl ditelluride reacted with phenylacetylene and 1,4-diphenyl-but-1-en-3-yne affording (Z)-phenyltelluro alkenes in good yields. (C) 2015 Elsevier Ltd. All rights reserved.