1-(3-iodo-4,5-dihydroselenophen-2-yl)hexan-1-ol | 1221975-35-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-iodo-4,5-dihydroselenophen-2-yl)hexan-1-ol
• 英文别名: 1-(4-Iodo-2,3-dihydroselenophen-5-yl)hexan-1-ol
• CAS: 1221975-35-4
• 化学式: C₁₀H₁₇IOSe
• 分子量: 359.109
• InChiKey: YNXIGHSJNSUGRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3-iodo-4,5-dihydroselenophen-2-yl)hexan-1-ol 、 4-甲苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到1-(3-(p-tolyl)-4,5-dihydroselenophen-2-yl)hexan-1-ol
  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：

  1-(butylselanyl)dec-3-yn-5-ol 在 碘 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到1-(3-iodo-4,5-dihydroselenophen-2-yl)hexan-1-ol
  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