butyl(4-phenylbut-3-ynyl)selane | 1221975-09-2

• 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: butyl(4-phenylbut-3-ynyl)selane
• 英文别名: 4-Butylselanylbut-1-ynylbenzene；4-butylselanylbut-1-ynylbenzene
• CAS: 1221975-09-2
• 化学式: C₁₄H₁₈Se
• 分子量: 265.257
• InChiKey: RRZOHIMLYUNRFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  butyl(4-phenylbut-3-ynyl)selane 在 四(三苯基膦)钯 、 碘 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(4-chlorophenyl)-5-phenyl-2,3-dihydroselenophene
  参考文献：
  名称：

  The potential antioxidant activity of 2,3-dihydroselenophene, a prototype drug of 4-aryl-2,3-dihydroselenophenes

  摘要：

  Here we present our results in palladium cross-coupling reaction of aryl boronic acids with 4-iodo-2, 3-dihydroselenophene derivatives. The cross-coupled products were obtained in satisfactory yields. A dehydrogenation of 4,5-diphenyl-2,3-dihydroselenophene was activated by DDQ and the 2,3-diarylselenophene was obtained in good yield. Regarding the antioxidant activity, the selenophene derivative 3a was effective in counteracting lipid and protein oxidation as well as scavenging ABTS radical. The findings of the present study indicate that 3a is a prototype for future drug development programs to treat disorders mediated by reactive oxygen species. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.01.005
• 作为产物：
  描述：

  正丁基锂 、 4-phenylbut-3-yn-1-yl 4-methylbenzenesulfonate 在 selenium 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 以85%的产率得到butyl(4-phenylbut-3-ynyl)selane
  参考文献：
  名称：

  Synthesis of 2,3-Dihydroselenophene and Selenophene Derivatives by Electrophilic Cyclization of Homopropargyl Selenides

  摘要：

  The synthesis of several highly functionalized 2,3-dihydroselenophenes from homopropargyl selenides via electrophilic cyclization is described. Electrophiles such as 12, ICI, and PhSeBr were used in a simple process employing CH2Cl2 as solvent at room temperature, which gave the cyclized products in high yields. 4-lodo-2,3-dihydroselenophenes obtained by this methodology were submitted to a dehydrogenation reaction using 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) to give 3-iodoselenophenes. 4-lodo-5-phenyl-2,3-dihydroselenophene was also submitted to the thiol copper-catalyzed and Heck-type reactions giving the desired products under mild reaction conditions.

  DOI：

  10.1021/ol1003753

文献信息

• Cyclization of Homopropargyl Chalcogenides by Copper(II) Salts: Selective Synthesis of 2,3-Dihydroselenophenes, 3-Arylselenophenes, and 3-Haloselenophenes/thiophenes
  作者：Ricardo F. Schumacher、Alisson R. Rosário、Marlon R. Leite、Gilson Zeni

  DOI：10.1002/chem.201302129

  日期：2013.9.23

  Copper(II) halide mediated cyclization of homopropargyl chalcogenides gave three types of chalcogenophene derivatives. Selective product formation was achieved by controlling solvent, temperature, and atmosphere. By using CuBr2 and 1,2‐dichloroethane at room temperature under ambient atmosphere, 4‐bromo dihydroselenophene derivatives were obtained, whereas CuBr2 and 1,2‐dichloroethane at reflux gave

  铜（II）卤化物介导的高炔丙基硫属元素化物的环化反应产生了三种类型的硫属元素衍生物。通过控制溶剂，温度和气氛来实现选择性产物的形成。通过在室温和环境气氛下于室温下使用CuBr 2和1,2-二氯乙烷，可制得4-溴二氢硒苯衍生物，而CuBr 2和1,2-二氯乙烷在回流条件下产生选择性2-取代的硒烯。当1,2-二氯乙烷被二甲基乙酰胺代替时，仅获得3-卤代硒代苯。还通过在Sonogashira条件下3-卤代亚硒基与末端炔烃的反应研究了硫属芴的多功能性，从而提供了交叉偶联的产物。此外，3-卤代亚硒基与硼酸的反应以良好的收率得到了相应的铃木型产物。