3-t-butoxy-2-trimethylstannylthiophene | 143584-42-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-t-butoxy-2-trimethylstannylthiophene
• 英文别名: trimethyl-[3-[(2-methylpropan-2-yl)oxy]thiophen-2-yl]stannane
• CAS: 143584-42-3
• 化学式: C₁₁H₂₀OSSn
• 分子量: 319.055
• InChiKey: BKGVTOZDRXHKAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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-溴吡啶 、 3-t-butoxy-2-trimethylstannylthiophene 在 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以13.7%的产率得到3-t-butoxy-2-(2-pyridyl)thiophene
  参考文献：
  名称：

  Pyridine-Substituted Hydroxythiophenes. I. Preparation of o-(2-, 3- and 4-pyridyl)-3-hydroxythiophenes.

  摘要：

  2-(2-, 3- and 4-pyridyl)-3-hydroxythiophenes and 4-(2-, 3- and 4-pyridyl)-3-hydroxythiophenes dagger have been prepared by hydrogen peroxide oxidation of the corresponding boronic esters. In the former case the boronic esters were obtained in three steps from 2,3-dibromothiophene via the corresponding 3-bromo-2-pyridylthiophenes synthesized by Pd(0)-catalyzed coupling between 3-bromo-2-trimethylstannylthiophene and the corresponding bromopyridines. In the latter case the known isomeric pyridylthiophenes were converted into the corresponding boronic esters in three steps via tribromo- and 3-bromo-4-pyridylthiophenes successively. 4-(3- and 4-pyridyl)thiophen-2(5H)-ones were also obtained in the syntheses of 4-(3- and 4-pyridyl)-3-hydroxythiophene. They are suggested to arise from rearrangement during the halogen-metal exchange. Spectroscopic investigations by H-1 NMR and IR show that these hydroxythiophene systems exist exclusively as enol forms.

  DOI：

  10.3891/acta.chem.scand.46-0654
• 作为产物：
  描述：

  3-tert.-Butyloxy-thiophen 、 三甲基氯化锡 在 正丁基锂 作用下， 以 乙醚 为溶剂， 以57%的产率得到3-t-butoxy-2-trimethylstannylthiophene
  参考文献：
  名称：

  Pyridine-Substituted Hydroxythiophenes. I. Preparation of o-(2-, 3- and 4-pyridyl)-3-hydroxythiophenes.

  摘要：

  2-(2-, 3- and 4-pyridyl)-3-hydroxythiophenes and 4-(2-, 3- and 4-pyridyl)-3-hydroxythiophenes dagger have been prepared by hydrogen peroxide oxidation of the corresponding boronic esters. In the former case the boronic esters were obtained in three steps from 2,3-dibromothiophene via the corresponding 3-bromo-2-pyridylthiophenes synthesized by Pd(0)-catalyzed coupling between 3-bromo-2-trimethylstannylthiophene and the corresponding bromopyridines. In the latter case the known isomeric pyridylthiophenes were converted into the corresponding boronic esters in three steps via tribromo- and 3-bromo-4-pyridylthiophenes successively. 4-(3- and 4-pyridyl)thiophen-2(5H)-ones were also obtained in the syntheses of 4-(3- and 4-pyridyl)-3-hydroxythiophene. They are suggested to arise from rearrangement during the halogen-metal exchange. Spectroscopic investigations by H-1 NMR and IR show that these hydroxythiophene systems exist exclusively as enol forms.

  DOI：

  10.3891/acta.chem.scand.46-0654