trans-2-phenoxymethyl-4-[(phenyltelluro)methyl]tetrahydrofuran

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: trans-2-phenoxymethyl-4-[(phenyltelluro)methyl]tetrahydrofuran
• 英文别名: (2S,4R)-2-(phenoxymethyl)-4-(phenyltellanylmethyl)oxolane
• 化学式: C₁₈H₂₀O₂Te
• 分子量: 395.956
• InChiKey: FGNKGSQCGNQSRB-WBVHZDCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  联苯二碲 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 乙二醇 为溶剂， 反应 0.1h， 生成 trans-2-phenoxymethyl-4-[(phenyltelluro)methyl]tetrahydrofuran
  参考文献：
  名称：

  Microwave-Assisted Group-Transfer Cyclization of Organotellurium Compounds

  摘要：

  Primary- and secondary-alkyl aryl tellurides, prepared by arenetellurolate ring-opening of epoxides/O-allylation, were found to undergo rapid (3 - 10 min) group-transfer cyclization to afford tetrahydrofuran derivatives in 60-74% yield when heated in a microwave cavity at 250 degreesC in ethylene glycol or at 180 degreesC in water. To go to completion, similar transformations had previously required extended photolysis in refluxing benzene containing a substantial amount of hexabutylditin. The only drawback of the microwave-assisted process was the loss in diastereoselectivity which is a consequence of the higher reaction temperature. Substitution in the Te-aryl moiety of the secondary-alkyl aryl tellurides (4-OMe, 4-H, 4-CF3) did not affect the outcome of the group-transfer reaction in ethylene glycol. However, at lower temperature, using water as a solvent, the CF3 derivative failed to react. The microwave-assisted group-transfer cyclization was extended to benzylic but not to primary- and secondary-alkyl phenyl selenides.

  DOI：

  10.1021/jo040155f

文献信息

• Microwave-Assisted Group-Transfer Cyclization of Organotellurium Compounds
  作者：Cecilia Ericsson、Lars Engman

  DOI：10.1021/jo040155f

  日期：2004.7.1

  Primary- and secondary-alkyl aryl tellurides, prepared by arenetellurolate ring-opening of epoxides/O-allylation, were found to undergo rapid (3 - 10 min) group-transfer cyclization to afford tetrahydrofuran derivatives in 60-74% yield when heated in a microwave cavity at 250 degreesC in ethylene glycol or at 180 degreesC in water. To go to completion, similar transformations had previously required extended photolysis in refluxing benzene containing a substantial amount of hexabutylditin. The only drawback of the microwave-assisted process was the loss in diastereoselectivity which is a consequence of the higher reaction temperature. Substitution in the Te-aryl moiety of the secondary-alkyl aryl tellurides (4-OMe, 4-H, 4-CF3) did not affect the outcome of the group-transfer reaction in ethylene glycol. However, at lower temperature, using water as a solvent, the CF3 derivative failed to react. The microwave-assisted group-transfer cyclization was extended to benzylic but not to primary- and secondary-alkyl phenyl selenides.