(4-Allyl-furan-3-ylmethoxy)-tert-butyl-dimethyl-silane | 125849-90-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (4-Allyl-furan-3-ylmethoxy)-tert-butyl-dimethyl-silane
• 英文别名: tert-butyl-dimethyl-[(4-prop-2-enylfuran-3-yl)methoxy]silane
• CAS: 125849-90-3
• 化学式: C₁₄H₂₄O₂Si
• 分子量: 252.429
• InChiKey: GSRHTABUSNGMDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.53
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  [2-[Tert-butyl(dimethyl)silyl]-4-prop-2-enylfuran-3-yl]methanol 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以91%的产率得到(4-Allyl-furan-3-ylmethoxy)-tert-butyl-dimethyl-silane
  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

文献信息

• The 1,4 C→O silyl migrations of various furan and thiophene systems
  作者：Patrick G. Spinazzé、Brian A. Keay

  DOI：10.1016/s0040-4039(00)99574-1

  日期：——
• SPINAZZE, PATRICK G.;KEAY, BRIAN A., TETRAHEDRON LETT., 30,(1989) N4, C. 1765-1768
  作者：SPINAZZE, PATRICK G.、KEAY, BRIAN A.

  DOI：——

  日期：——