2,5-diphenyl-3-(trimethylsiloxy)thiophene | 588729-00-4

• 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: 2,5-diphenyl-3-(trimethylsiloxy)thiophene
• 英文别名: (2,5-Diphenylthiophen-3-yl)oxy-trimethylsilane
• CAS: 588729-00-4
• 化学式: C₁₉H₂₀OSSi
• 分子量: 324.519
• InChiKey: YTLRCPQACBOXNP-UHFFFAOYSA-N

物化性质

• 沸点：
  402.1±45.0 °C(Predicted)
• 密度：
  1.073±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-diphenyl-3-(trimethylsiloxy)thiophene 以 氯仿 为溶剂， 生成 2,5-diphenyl-3-hydroxythiophene
  参考文献：
  名称：

  1,4-Silatropy of S-α-Silylbenzyl Thioesters:  A Convenient Route to Silyl Enol and Dienol Ethers Accompanied by C−C Bond Formation via Thiocarbonyl Ylides

  摘要：

  A novel convenient method for the generation of thiocarbonyl ylides from readily accessible starting materials and the first synthetic application of in situ generated ylides in the synthesis of silyl enol and dienol ethers, accompanied by C-C bond formation, is described. Under completely neutral conditions without any catalyst or additive, thermal reactions of S-alpha-silylbenzyl thioesters in sealed tubes at 180 degreesC provided silyl enol and dienol ethers in good to excellent yields with high stereoselectivities. This procedure consists of a multistep reaction in a one-pot process, i.e., 1,4-silatropy of S-alpha-silylbenzyl thioesters to give thiocarbonyl ylides, 1,3-electrocyclization of the ylides to give thiiranes, and the extrusion of sulfur from thiiranes to give silyl enol and dienol ethers.

  DOI：

  10.1021/jo026211z
• 作为产物：
  描述：

  S-α-trimethylsilylbenzyl (E)-thiocinnamate 在 sulfur 作用下， 以 苯 为溶剂， 反应 34.0h， 以61%的产率得到2,5-diphenyl-3-(trimethylsiloxy)thiophene
  参考文献：
  名称：

  从二烯醇甲硅烷基醚和元素硫到噻吩的简便[4 + 1]型合成路线

  摘要：

  描述了一种通过容易获得的二烯醇甲硅烷基醚与元素硫反应合成噻吩衍生物的简便方法。当在MS4A存在下于180°C加热时，二烯丙基甲硅烷基醚和元素硫可提供3-甲硅烷氧基噻吩衍生物，产率最高可达98％。在该反应中，噻吩衍生物可能是通过1,2-二硫烷和八元环四硫化物形成的。

  DOI：

  10.1016/j.tet.2005.10.024

文献信息

• 1,4-Silatropy of <i>S</i>-α-Silylbenzyl Thioesters:  A Convenient Route to Silyl Enol and Dienol Ethers Accompanied by C−C Bond Formation via Thiocarbonyl Ylides
  作者：Jinil Choi、Eiichiro Imai、Masatoshi Mihara、Yoji Oderaotoshi、Satoshi Minakata、Mitsuo Komatsu

  DOI：10.1021/jo026211z

  日期：2003.8.1

  A novel convenient method for the generation of thiocarbonyl ylides from readily accessible starting materials and the first synthetic application of in situ generated ylides in the synthesis of silyl enol and dienol ethers, accompanied by C-C bond formation, is described. Under completely neutral conditions without any catalyst or additive, thermal reactions of S-alpha-silylbenzyl thioesters in sealed tubes at 180 degreesC provided silyl enol and dienol ethers in good to excellent yields with high stereoselectivities. This procedure consists of a multistep reaction in a one-pot process, i.e., 1,4-silatropy of S-alpha-silylbenzyl thioesters to give thiocarbonyl ylides, 1,3-electrocyclization of the ylides to give thiiranes, and the extrusion of sulfur from thiiranes to give silyl enol and dienol ethers.
• A facile [4+1] type synthetic route to thiophenes from dienol silyl ethers and elemental sulfur
  作者：Yukihiro Kasano、Aoi Okada、Daisuke Hiratsuka、Yoji Oderaotoshi、Satoshi Minakata、Mitsuo Komatsu

  DOI：10.1016/j.tet.2005.10.024

  日期：2006.1

  A facile method for the synthesis of thiophene derivatives via the reaction of readily accessible dienol silyl ethers with elemental sulfur is described. Dienol silyl ethers and elemental sulfur, when heated at 180 °C in the presence of MS4A, provided 3-siloxythiophene derivatives in yields up to 98%. In this reaction, thiophene derivatives might be formed through 1,2-dithiines and eight-membered cyclic

  描述了一种通过容易获得的二烯醇甲硅烷基醚与元素硫反应合成噻吩衍生物的简便方法。当在MS4A存在下于180°C加热时，二烯丙基甲硅烷基醚和元素硫可提供3-甲硅烷氧基噻吩衍生物，产率最高可达98％。在该反应中，噻吩衍生物可能是通过1,2-二硫烷和八元环四硫化物形成的。