5,5'-dimethyl-2,2'-dithienyl diselenide | 282542-90-9

• 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: 5,5'-dimethyl-2,2'-dithienyl diselenide
• 英文别名: 1,2-bis(5-methylthiophen-2-yl)diselane；2-Methyl-5-[(5-methylthiophen-2-yl)diselanyl]thiophene
• CAS: 282542-90-9
• 化学式: C₁₀H₁₀S₂Se₂
• 分子量: 352.241
• InChiKey: HDCHIDOJXANVQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲基呋喃 、 5,5'-dimethyl-2,2'-dithienyl diselenide 在 碘苯二乙酸 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以75%的产率得到2-methyl-5-[(5-methyl-2-thienyl)seleno]furan
  参考文献：
  名称：

  Electrophilic 2-Thienylselenenylation of Thiophene. Preparation of Oligo(seleno-2,5-thienylenes)

  摘要：

  The substitution reactions of thiophene and 2-methylthiophene with the electrophilic selenenylating agent produced from the 2.2'-dithienyl diselenide by oxidation with iodobenzene diacetate involve only the alpha-positions and give rise to the formation of oligo(seleno-2,5-thienylenes). Products deriving from the attack at the alpha-positions of thiophene and 2-methylthiophene were also observed starting from the 5,5'-dimethyl-2,2'-dithienyl diselenide. The same electrophilic reagents reacted with furan and 2-methylfuran to afford a mixture of the mono- and di-substituted compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00245-3
• 作为产物：
  描述：

  2-lithio-5-methylthiophene 在 selenium 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.5h， 生成 5,5'-dimethyl-2,2'-dithienyl diselenide
  参考文献：
  名称：

  Electrophilic 2-Thienylselenenylation of Thiophene. Preparation of Oligo(seleno-2,5-thienylenes)

  摘要：

  The substitution reactions of thiophene and 2-methylthiophene with the electrophilic selenenylating agent produced from the 2.2'-dithienyl diselenide by oxidation with iodobenzene diacetate involve only the alpha-positions and give rise to the formation of oligo(seleno-2,5-thienylenes). Products deriving from the attack at the alpha-positions of thiophene and 2-methylthiophene were also observed starting from the 5,5'-dimethyl-2,2'-dithienyl diselenide. The same electrophilic reagents reacted with furan and 2-methylfuran to afford a mixture of the mono- and di-substituted compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00245-3

文献信息

• Iodine mediated synthesis of diaryl diselenides using SeO₂ as a selenium source
  作者：Dileep Kommula、Qing Li、Siyang Ning、Wujun Liu、Qian Wang、Zongbao K. Zhao

  DOI：10.1080/00397911.2020.1728775

  日期：2020.4.2

  Abstract A simple, eco-friendly and convenient procedure has been developed for the synthesis of diphenyl diselinides from readily available aryl boronic acids by reaction with SeO2 in the presence of iodine under simple conditions. The methodology is reported about 19 examples and applicable to a broad scope of aryl boronic acids containing electron-rich and electron-poor substituents. Apart from

  摘要 已开发出一种简单、环保且方便的方法，用于在简单条件下，在碘存在下与 SeO2 反应，从易得的芳基硼酸合成二苯基二硒化物。该方法报告了大约 19 个实例，适用于广泛的含有富电子和缺电子取代基的芳基硼酸。除了更温和和环境友好的条件外，该合成方案还包括一种新颖、可靠的方法，以提供所需的二芳基二硒化物的高产率。图形概要
• Electrophilic 2-Thienylselenenylation of Thiophene. Preparation of Oligo(seleno-2,5-thienylenes)
  作者：Marcello Tiecco、Lorenzo Testaferri、Luana Bagnoli、Francesca Marini、Andrea Temperini、Cristina Tomassini、Claudio Santi

  DOI：10.1016/s0040-4020(00)00245-3

  日期：2000.5

  The substitution reactions of thiophene and 2-methylthiophene with the electrophilic selenenylating agent produced from the 2.2'-dithienyl diselenide by oxidation with iodobenzene diacetate involve only the alpha-positions and give rise to the formation of oligo(seleno-2,5-thienylenes). Products deriving from the attack at the alpha-positions of thiophene and 2-methylthiophene were also observed starting from the 5,5'-dimethyl-2,2'-dithienyl diselenide. The same electrophilic reagents reacted with furan and 2-methylfuran to afford a mixture of the mono- and di-substituted compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.