but-3-ynyl(butyl)selane | 1221975-07-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: but-3-ynyl(butyl)selane
• 英文别名: 1-But-3-ynylselanylbutane
• CAS: 1221975-07-0
• 化学式: C₈H₁₄Se
• 分子量: 189.159
• InChiKey: FKMSEAZDHFXFLB-UHFFFAOYSA-N

物化性质

• 沸点：
  210.1±23.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  but-3-ynyl(butyl)selane 在 碘 作用下， 以 二氯甲烷 为溶剂， 以67%的产率得到4-iodo-2,3-dihydroselenophene
  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
• 作为产物：
  描述：

  正丁基锂 、 对甲苯磺酸 3-丁炔酯 在 selenium 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 以90%的产率得到but-3-ynyl(butyl)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

• The potential antioxidant activity of 2,3-dihydroselenophene, a prototype drug of 4-aryl-2,3-dihydroselenophenes
  作者：Ricardo F. Schumacher、Alisson R. Rosário、Ana C.G. Souza、Carmine I. Acker、Cristina W. Nogueira、Gilson Zeni

  DOI：10.1016/j.bmc.2011.01.005

  日期：2011.2

  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.