4-iodo-5-phenyl-2,3-dihydroselenophene | 1221975-27-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-iodo-5-phenyl-2,3-dihydroselenophene
• 英文别名: 2-phenyl-3-iodo-4,5-dihydroselenophene
• CAS: 1221975-27-4
• 化学式: C₁₀H₉ISe
• 分子量: 335.046
• InChiKey: WAWIKORYXLYBOT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  12
• 可旋转键数：
  1
• 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：

  4-iodo-5-phenyl-2,3-dihydroselenophene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以77%的产率得到2-phenyl-3-iodoselenophene
  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：

  butyl(4-phenylbut-3-ynyl)selane 在 碘 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到4-iodo-5-phenyl-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

文献信息

• Synthesis and Reactivity of 3-Alkynyldihydroselenophene Derivatives
  作者：Alisson R. Rosário、Ricardo F. Schumacher、Bibiana M. Gay、Paulo H. Menezes、Gilson Zeni

  DOI：10.1002/ejoc.201000588

  日期：2010.10

  We present herein our results on the synthesis of 3-alkynyl-dihydroselenophenes by palladium-catalyzed Sonogashira cross-coupling of 3-iododihydroselenophenes with different alkynes under mild conditions in good to excellent yields. The developed protocol tolerated a wide range of functional groups in the dihydroselenophenes and alkynes. These 3-alkynyldihydroselenophenes, bearing the chalcogen group

  我们在此展示了我们在温和条件下通过钯催化的 Sonogashira 与不同炔烃的交叉偶联合成 3-炔基-二氢硒酚的结果，产率良好至极好。开发的协议可以容忍二氢硒酚和炔烃中的各种官能团。这些带有硫属元素基团的 3-炔基二氢硒酚在用 I 2 处理时经历了高度选择性的分子内环化，以提供稠合的二氢硒酚 [2,3,b]-硒酚环。此外，通过该方法获得的 3-炔基二氢硒吩还通过使用 DDQ 进行氧化反应，以中等产率得到芳香硒吩。
• 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.