2,5-diphenyl-3-(4-chlorophenylseleno)-selenophene | 1071469-51-6

• 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: 2,5-diphenyl-3-(4-chlorophenylseleno)-selenophene
• 英文别名: 2,5-diphenyl-3-(4-chlorophenylseleno)selenophene；3-(4-Chlorophenyl)selanyl-2,5-diphenylselenophene
• CAS: 1071469-51-6
• 化学式: C₂₂H₁₅ClSe₂
• 分子量: 472.734
• InChiKey: FHTHYXFOQBAVAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• 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：

  (1-butylselanyl-4-phenylbut-1-en-3-ynyl)benzene 、 双(4-氯苯基)二硒化物 在 copper(l) iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 10.0h， 以89%的产率得到2,5-diphenyl-3-(4-chlorophenylseleno)-selenophene
  参考文献：
  名称：

  Copper Iodide-Catalyzed Cyclization of (Z)-Chalcogenoenynes

  摘要：

  We present here our results of the efficient copper-catalyzed cyclizations of chalcogenoenynes and establish a route to obtain 3-substituted chalcogenophenes in good to excellent yields. In addition, the obtained chalcogenophenes were readily transformed to more complex products using the palladium-catalyzed cross-coupling reactions with boronic acids to give Suzuki-type products in good yields.

  DOI：

  10.1021/ol802060f

文献信息

• 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。
• Copper Iodide-Catalyzed Cyclization of (<i>Z</i>)-Chalcogenoenynes
  作者：André L. Stein、Diego Alves、Juliana T. da Rocha、Cristina W. Nogueira、Gilson Zeni

  DOI：10.1021/ol802060f

  日期：2008.11.6

  We present here our results of the efficient copper-catalyzed cyclizations of chalcogenoenynes and establish a route to obtain 3-substituted chalcogenophenes in good to excellent yields. In addition, the obtained chalcogenophenes were readily transformed to more complex products using the palladium-catalyzed cross-coupling reactions with boronic acids to give Suzuki-type products in good yields.