2,5-bis(trimethylsilyl)-3,4-ethylenedioxythiophene | 195602-16-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-bis(trimethylsilyl)-3,4-ethylenedioxythiophene
• 英文别名: Trimethyl-(5-trimethylsilyl-2,3-dihydrothieno[3,4-b][1,4]dioxin-7-yl)silane
• CAS: 195602-16-5
• 化学式: C₁₂H₂₂O₂SSi₂
• 分子量: 286.542
• InChiKey: WRMQHSZGHQWESX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,5-bis(trimethylsilyl)-3,4-ethylenedioxythiophene 在 四丁基氟化铵 作用下， 以70%的产率得到3,4-乙烯二氧噻吩
  参考文献：
  名称：

  3,4-Ethylenedioxythiophene and 3,4-Ethylenedioxyselenophene: Synthesis and Reactivity of C_α−Si Bond

  摘要：

  A synthetic approach to synthesize EDOT and EDOS from a common precursor 5 is reported. The method involves zirconocene dichloride mediated reaction of a common diyne 5 followed by treatment with disulfur dichloride (S2Cl2) and in situ prepared selenium dichloride (SeCl2). The higher lability of alpha-trimethylsilyl group in EDOS compared to EDOT is explained using DFT calculations.

  DOI：

  10.1021/jo100756k
• 作为产物：
  描述：

  Trimethyl-[2-[2-(2-trimethylsilylethynoxy)ethoxy]ethynyl]silane 在 正丁基锂 、 二氯化二硫 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以40%的产率得到2,5-bis(trimethylsilyl)-3,4-ethylenedioxythiophene
  参考文献：
  名称：

  3,4-Ethylenedioxythiophene and 3,4-Ethylenedioxyselenophene: Synthesis and Reactivity of C_α−Si Bond

  摘要：

  A synthetic approach to synthesize EDOT and EDOS from a common precursor 5 is reported. The method involves zirconocene dichloride mediated reaction of a common diyne 5 followed by treatment with disulfur dichloride (S2Cl2) and in situ prepared selenium dichloride (SeCl2). The higher lability of alpha-trimethylsilyl group in EDOS compared to EDOT is explained using DFT calculations.

  DOI：

  10.1021/jo100756k

文献信息

• 3,4-Ethylenedioxythiophene and 3,4-Ethylenedioxyselenophene: Synthesis and Reactivity of C_α−Si Bond
  作者：Soumyajit Das、Pradip Kumar Dutta、Snigdha Panda、Sanjio S. Zade

  DOI：10.1021/jo100756k

  日期：2010.7.16

  A synthetic approach to synthesize EDOT and EDOS from a common precursor 5 is reported. The method involves zirconocene dichloride mediated reaction of a common diyne 5 followed by treatment with disulfur dichloride (S2Cl2) and in situ prepared selenium dichloride (SeCl2). The higher lability of alpha-trimethylsilyl group in EDOS compared to EDOT is explained using DFT calculations.