2-methyl-5-[(5-methyl-2-thienyl)seleno]thiophene

• 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-[(5-methyl-2-thienyl)seleno]thiophene
• 英文别名: bis(5-methylthiophen-2-yl)selane；2-Methyl-5-(5-methylthiophen-2-yl)selanylthiophene
• 化学式: C₁₀H₁₀S₂Se
• 分子量: 273.281
• InChiKey: ZWFWOHRBCWUBOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  13
• 可旋转键数：
  2
• 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

• 作为产物：
  描述：

  2-lithio-5-methylthiophene 在 selenium 、 碘苯二乙酸 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 25.5h， 生成 2-methyl-5-[(5-methyl-2-thienyl)seleno]thiophene
  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

• Potassium selenocyanate as an efficient selenium source in C–Se cross-coupling catalyzed by copper iodide in water
  作者：A. Vijay Kumar、V. Prakash Reddy、C. Suresh Reddy、K. Rama Rao

  DOI：10.1016/j.tetlet.2011.05.068

  日期：2011.8

  An efficient and conceptually new protocol for C–Se cross coupling of potassium selenocyanate with aryl halides via copper-catalyzed cascade reaction has been developed in water. Utilizing this protocol, a variety of aryl and heteroaryl halides were reacted with potassium selenocyanate to afford the corresponding diaryl selenides in moderate to good yields.

  在水中已开发出一种有效且概念上新颖的方案，用于通过铜催化的级联反应将硒氰酸钾与芳基卤化物进行C-Se交叉偶联。利用该方案，使各种芳基和杂芳基卤化物与硒氰酸钾反应，以中等至良好的产率得到相应的二芳基硒化物。
• Metal free synthesis of diaryl selenides using SeO 2 as a selenium source
  作者：R. Uday Kumar、K. Harsha Vardhan Reddy、G. Satish、K. Swapna、Y.V.D. Nageswar

  DOI：10.1016/j.tetlet.2016.07.075

  日期：2016.9

  efficient, and eco-friendly synthetic protocol has been developed for the preparation of diaryl selenium compounds. To the best of our knowledge, this is the first Letter on the use of selenium dioxide as selenium source for the synthesis of diaryl selenides. Compared with other selenium sources the new source SeO2 gives an environment-friendly and low-cost synthetic route, which may be useful for

  已经开发了一种简单，有效且环保的合成方案，用于制备二芳基硒化合物。就我们所知，这是关于使用二氧化硒作为硒源合成二芳基硒化物的第一封信。与其他硒源相比，新的SeO 2源提供了一种环保且低成本的合成路线，这可能对大规模合成有用。
• Unexpected C−Se Cross-Coupling Reaction: Copper Oxide Catalyzed Synthesis of Symmetrical Diaryl Selenides via Cascade Reaction of Selenourea with Aryl Halides/Boronic Acids
  作者：V. Prakash Reddy、A. Vijay Kumar、K. Rama Rao

  DOI：10.1021/jo102017g

  日期：2010.12.17

  Selenourea is used as an effective selenium surrogate in the C−Se cross-coupling reaction catalyzed by copper oxide nanoparticles under ligand free conditions. This protocol has been utilized for the synthesis of a variety of symmetrical diaryl selenides in good to excellent yields from the readily available aryl halides/boronic acids.

  在无配体条件下，氧化铜纳米粒子催化的硒化硒在C-Se交叉偶联反应中用作有效的硒替代物。该方案已被用于从容易获得的芳基卤化物/硼酸以良好或优异的产率合成多种对称的二芳基硒化物。
• 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.