(2,5-diphenyl-selenophen-3-yl)-(p-methoxy-phenyl)-methanol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2,5-diphenyl-selenophen-3-yl)-(p-methoxy-phenyl)-methanol
• 英文别名: (2,5-diphenylselenophen-3-yl)-(p-methoxyphenyl)methanol；(2,5-Diphenylselenophen-3-yl)-(4-methoxyphenyl)methanol
• 化学式: C₂₄H₂₀O₂Se
• 分子量: 419.382
• InChiKey: AGJXEGSAMKEOOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1，4-二苯基丁二炔 在 sodium tetrahydroborate 、 正丁基锂 、 碘 作用下， 以 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.25h， 生成 (2,5-diphenyl-selenophen-3-yl)-(p-methoxy-phenyl)-methanol
  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

• 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。