3-(5-tert-butyldimethylsilyl)furylmethanol | 601470-46-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 3-(5-tert-butyldimethylsilyl)furylmethanol
• 英文别名: [5-[tert-butyl(dimethyl)silyl]furan-3-yl]methanol
• CAS: 601470-46-6
• 化学式: C₁₁H₂₀O₂Si
• 分子量: 212.364
• InChiKey: WWMUGLFARAWKAP-UHFFFAOYSA-N

物化性质

• 沸点：
  189.1±10.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  33.37
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(5-tert-butyldimethylsilyl)furylmethanol 在 吡啶 、 三溴化磷 作用下， 以 乙醚 、 苯 为溶剂， 反应 3.17h， 生成 3-(5-tert-butyldimethylsilylfuryl)methyltriphenylphosphonium bromide
  参考文献：
  名称：

  Development of new Wittig reagent, silylfuranmethylid, and its reactivity

  摘要：

  New Wittig reagents, furanmethylids b-e were successfully developed. Their preparation, reactivity, and application toward the natural products synthesis are described in detail. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00763-4
• 作为产物：
  描述：

  3-糠酸 在 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 6.0h， 生成 3-(5-tert-butyldimethylsilyl)furylmethanol
  参考文献：
  名称：

  Regioselective Preparation of 2,4-, 3,4-, and 2,3,4-Substituted Furan Rings. 1. [1,4] O → C and [1,4] C → O Silyl Migrations of Silyl Ethers and Esters Attached to Furan and Thiophene Rings

  摘要：

  [1,4] O --> C and [1,4] C --> O rearrangements are described for a variety of furans and thiophenes. Treatment of 3-((silyloxy)methyl)furans and -thiophenes with n-BuLi in HMPA provided 2-silylated-3-(hydroxymethyl)furans and -thiophenes in good to excellent yields. The reaction was shown by crossover studies to proceed via an intramolecular [1,4] O --> C silyl migration. Silyl esters of 3-furoic acids also underwent an intramolecular [1,4] O --> C silyl migration to provide 2-silylated-3-furoic acids in moderate to good yield when treated with a mixture of LDA and HMPA. Finally, the above silyl migrations were shown to be reversible. Treatment of 2-silylated-3-(hydroxymethyl)furans and -thiophenes with NaH in DMF provided 3-((silyloxy)methyl)furans and -thiophenes in excellent yields via a [1,4] C --> O silyl migration. The [1,4] C --> O silyl migration was also shown to be an intramolecular process by a crossover study.

  DOI：

  10.1021/jo971097j