(Z)-1-(n-butylseleno)-1,4-diphenyl-but-1-en-3-yne | 685570-02-9

• 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-(n-butylseleno)-1,4-diphenyl-but-1-en-3-yne
• 英文别名: (1-butylselanyl-4-phenyl-but-1-en-3-ynyl)benzene；[(Z)-1-butylselanyl-4-phenylbut-1-en-3-ynyl]benzene
• CAS: 685570-02-9
• 化学式: C₂₀H₂₀Se
• 分子量: 339.339
• InChiKey: SSHPXGUETZDXGW-SILNSSARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  (Z)-1-(n-butylseleno)-1,4-diphenyl-but-1-en-3-yne 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以93%的产率得到2,5-diphenyl-3-iodoselenophene
  参考文献：
  名称：

  3-碘硒醚衍生物：Negishi交叉偶联反应的通用底物

  摘要：

  在室温下，在THF中催化量的Pd（PPh 3）4存在下，3-碘硒醚衍生物与几种有机锌化合物直接进行Negishi交叉偶联反应。该交叉偶联反应在温和条件下干净地进行，并允许以高收率形成多芳族化合物。

  DOI：

  10.1016/j.tetlet.2007.11.070
• 作为产物：
  描述：

  1，4-二苯基丁二炔 在 sodium tetrahydroborate 、 碘 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 5.42h， 生成 (Z)-1-(n-butylseleno)-1,4-diphenyl-but-1-en-3-yne
  参考文献：
  名称：

  Electrophilic Cyclization of (Z)-Selenoenynes:  Synthesis and Reactivity of 3-Iodoselenophenes

  摘要：

  We present here our results of the electrophilic cyclization reaction of (Z)-selenoenynes with different electrophiles such as I-2, ICl, PhSeBr, and PhSeCl. The cyclization reaction proceeded cleanly under mild reaction conditions, and 3-substituted selenophenes were formed in moderate to excellent yields. We observed that the nature of solvent and structure of (Z)-selenoenyne were important to the cyclization reaction. In addition, the obtained 3-iodoselenophenes were readily transformed to more complex products using a metal-halogen exchange reaction with n-BuLi and trapping the intermediate formed with aldehydes, furnishing the desired secondary alcohols in good yields. Conversely, using the palladium or copper catalyzed cross-coupling reactions with terminal alkynes or alkyl alcohols, we were able to convert 3-iodoselenophene to Sonogashira or Ullmann type products, respectively, in good yields.

  DOI：

  10.1021/jo070835t

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。
• Synthesis and antidepressant-like activity of selenophenes obtained viairon(iii)–PhSeSePh-mediated cyclization of Z-selenoenynes
  作者：Bibiana M. Gai、André L. Stein、Juliano A. Roehrs、Filipe N. Bilheri、Cristina W. Nogueira、Gilson Zeni

  DOI：10.1039/c1ob06548c

  日期：——

  We present here the synthesis and antidepressant-like action of a series of 2,5-disubstituted-3-(organoseleno)-selenophenes prepared by a novel synthetic route, the FeCl3–diorganyl dichalcogenide-mediated intramolecular cyclization of (Z)-chalcogenoenynes. The cyclized products were obtained in good yields. The results showed that 2c, 2d, 2e and 2o, evaluated in the mouse forced-swimming test, elicited an antidepressant-like activity. The studies clearly show that the phenyl group at the 2-position and an organoselenium group at the 3-position of the selenophene ring are essential for the antidepressant-like activity of selenophenes. A close inspection of the results also revealed that the fluorophenyl portion in the organoselenium group is fundamental for the antidepressant-like action of this class of organochalcogens.

  我们在此介绍了一系列 2,5-二取代-3-（有机硒）-硒苯的合成和抗抑郁样作用，这些硒苯是通过一种新的合成路线，即 FeCl3âdiorganyl dichalcogenide-mediated intramolecular cyclization of (Z)-chalcogenoenynes 制备的。环化产物的收率很高。结果表明，在小鼠强迫游泳试验中评估的 2c、2d、2e 和 2o 具有类似抗抑郁的活性。这些研究清楚地表明，硒吩环 2 位上的苯基和 3 位上的有机硒基团是硒吩类抗抑郁活性的关键。仔细观察研究结果还发现，有机硒基团中的氟苯基部分是这类有机致癌物抗抑郁作用的基础。
• Palladium-Catalyzed Cross-Coupling Reaction of 3-Iodoselenophenes with Boronic Acids
  作者：Gilson Zeni、Daniela Barancelli、Diego Alves、Patrícia Prediger、Eluza Stangherlin、Cristina Nogueira

  DOI：10.1055/s-2007-992383

  日期：2008.1

  The Suzuki cross-coupling of 3-iodoselenophenes with boronic acids in the presence of catalytic amount of palladium salt is described. This cross-coupling reaction proceeded cleanly under mild conditions and was performed with aryl boronic acids bearing electron-withdrawing, electron-donating, and neutral substituents, furnishing the correspondents products in moderate to good yields.

  描述了在催化量的钯盐存在下 3-碘硒酚与硼酸的 Suzuki 交叉偶联。这种交叉偶联反应在温和的条件下干净地进行，并用带有吸电子、给电子和中性取代基的芳基硼酸进行，以中等至良好的产率提供相应的产物。
• Copper(II)-Mediated Intramolecular Cyclization of (Z)-Chalcogenoenynes: Synthesis of 3-Halochalcogenophene Derivatives
  作者：Daniela A. Barancelli、Ricardo F. Schumacher、Marlon R. Leite、Gilson Zeni

  DOI：10.1002/ejoc.201100992

  日期：2011.11

  We present our results on the cyclization of (Z)-chalcogenoenynes mediated by copper(II) salts to afford 3-halochalcogenophenes in satisfactory yields through an intramolecular 5-endo-dig cyclization. The methodology was carried out using CuCl2 at 50 °C or CuBr2 at room temperature under an ambient atmosphere. The reaction took place under very mild reaction conditions and tolerated considerable functionality

  我们展示了由铜 (II) 盐介导的 (Z)-硫属元素烯环化的结果，通过分子内 5-endo-dig 环化以令人满意的产率提供 3-卤代硫属元素烯。该方法是在 50 °C 下使用 CuCl2 或在室温下在环境气氛下使用 CuBr2 进行的。该反应在非常温和的反应条件下进行并且耐受相当大的官能度。在钯催化的与硼酸的交叉偶联反应中，将一种 3-溴-硒吩衍生物用作底物，以良好的收率得到 Suzuki 型产物。
• Butyltellurium Tribromide: A Suitable Electrophilic Source to Cyclization Reactions
  作者：Gilson Zeni、Diego Alves、Marina Prigol、Cristina Nogueira

  DOI：10.1055/s-2008-1042926

  日期：2008.4

  We present here our results of the electrophilic cyclization reaction of (Z)-chalcogenoenynes using butyltellurium tribromide as an electrophilic source. The cyclization reaction proceeded cleanly under mild reaction conditions and 3-(butyltellanyl)chalcogenophenes were formed in moderate to excellent yields. Subsequent, using these heterocycles as substrate to palladium-catalyzed cross-coupling reactions a new carbon-carbon bond was formed in good yields.

  我们在此介绍使用三溴化丁基碲作为亲电源对 (Z)- 卤代烯炔进行亲电环化反应的结果。环化反应在温和的反应条件下顺利进行，生成的 3-(丁基碲基)链烯的产率为中等到极好。随后，以这些杂环为底物，在钯催化下进行交叉偶联反应，以良好的收率形成了新的碳-碳键。