2-methyl-5-(phenylseleno)thiophene | 158956-96-8

• 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-methyl-5-(phenylseleno)thiophene
• 英文别名: 2-methyl-5-(phenylselanyl)thiophene；2-methyl-5-phenylselanylthiophene
• CAS: 158956-96-8
• 化学式: C₁₁H₁₀SSe
• 分子量: 253.226
• InChiKey: WVJXPYJVADKIRI-UHFFFAOYSA-N

物化性质

• 沸点：
  329.9±30.0 °C(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.71
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-methyl-5-(phenylseleno)thiophene 在 ammonium peroxydisulfate 作用下， 以 乙腈 为溶剂， 生成 2-methyl-3,4,5-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
• 作为产物：
  描述：

  2-甲基噻吩 、 二苯基二硒醚 在 yttrium(III) trifluoroacetate 、 N,N,N,N-tetraethylammonium tetrafluoroborate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以80%的产率得到2-methyl-5-(phenylseleno)thiophene
  参考文献：
  名称：

  Electrochemical Radical Selenylation of Alkenes and Arenes via Se–Se Bond Activation

  摘要：

  DOI：

  10.1021/acs.orglett.1c02661

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.
• Electrochemical Radical Selenylation of Alkenes and Arenes via Se–Se Bond Activation
  作者：Li Sun、Liwei Wang、Hesham Alhumade、Hong Yi、Hu Cai、Aiwen Lei

  DOI：10.1021/acs.orglett.1c02661

  日期：2021.10.15