2,3,5-tris(phenylseleno)thiophene | 158956-94-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2,3,5-tris(phenylseleno)thiophene
• 英文别名: 2,3,5-tris(phenylselenenyl)thiophene；2,3,5-Tris(phenylselanyl)thiophene
• CAS: 158956-94-6
• 化学式: C₂₂H₁₆SSe₃
• 分子量: 549.315
• InChiKey: MPULCWHEMVPXJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3,5-tris(phenylseleno)thiophene 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以100%的产率得到phenyl 3-thienyl selenide
  参考文献：
  名称：

  Preparation and Interconversion of Phenylselenenylated and Alkylselenenylated Aromatic Compounds

  摘要：

  Phenylselenenyl and alkylselenenyl sulfates were found to efficiently and mildly introduce one or several phenylselenenyl or alkylselenenyl groups into activated aromatic or heteroaromatic compounds. When treated with methylselenenyl sulfate, veratrole and 2,2',3,3'-tetramethoxybiphenyl afforded 2,3,7,8-tetramethoxyselenanthrene and 2,3,7,8-tetramethoxy-dibenzoselenophene, respectively, via oxidative demethylation at selenium/cyclization. Phenyl-selenenylated thiophenes were selectively hydrodeselenenated at the 2- and/or 5-positions by treatment with the appropriate amount of n-butyllithium at -78 degrees C followed by hydrolysis.

  DOI：

  10.3987/com-95-7377
• 作为产物：
  描述：

  二苯基二硒醚 、 2,5-bis(phenylseleno)thiophene 在 ammonium peroxydisulfate 作用下， 以 乙腈 为溶剂， 以15%的产率得到2,3,5-tris(phenylseleno)thiophene
  参考文献：
  名称：

  Electrophilic phenylselenenylation of thiophenes. Synthesis of poly(phenylseleno)thiophenes.

  摘要：

  The phenylselenenyl sulfate, generated from the oxidation of diphenyl diselenide with ammonium persulfate, easily effects electrophilic aromatic substitution reactions on thiophene, 2-and 3-methylthiophenes and on 3-bromothiophene. The phenylseleno group activates the substrate to further substitution. Under controlled experimental conditions, it is thus possible to introduce the desired number of phenylseleno groups into the thiophene ring.

  DOI：

  10.1016/s0040-4020(01)89595-8

文献信息

• Electrophilic phenylselenenylation of thiophenes. Synthesis of poly(phenylseleno)thiophenes.
  作者：Marcello Tiecco、Lorenzo Testaferri、Marco Tingoli、Francesca Marini、Stefania Mariggiò

  DOI：10.1016/s0040-4020(01)89595-8

  日期：1994.1

  The phenylselenenyl sulfate, generated from the oxidation of diphenyl diselenide with ammonium persulfate, easily effects electrophilic aromatic substitution reactions on thiophene, 2-and 3-methylthiophenes and on 3-bromothiophene. The phenylseleno group activates the substrate to further substitution. Under controlled experimental conditions, it is thus possible to introduce the desired number of phenylseleno groups into the thiophene ring.
• Preparation and Interconversion of Phenylselenenylated and Alkylselenenylated Aromatic Compounds
  作者：Lars Engman、Per Eriksson

  DOI：10.3987/com-95-7377

  日期：——

  Phenylselenenyl and alkylselenenyl sulfates were found to efficiently and mildly introduce one or several phenylselenenyl or alkylselenenyl groups into activated aromatic or heteroaromatic compounds. When treated with methylselenenyl sulfate, veratrole and 2,2',3,3'-tetramethoxybiphenyl afforded 2,3,7,8-tetramethoxyselenanthrene and 2,3,7,8-tetramethoxy-dibenzoselenophene, respectively, via oxidative demethylation at selenium/cyclization. Phenyl-selenenylated thiophenes were selectively hydrodeselenenated at the 2- and/or 5-positions by treatment with the appropriate amount of n-butyllithium at -78 degrees C followed by hydrolysis.