[2,5-bis[dimethyl(propan-2-yl)silyl]thiophen-3-yl]methanol | 117657-74-6

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: [2,5-bis[dimethyl(propan-2-yl)silyl]thiophen-3-yl]methanol
• CAS: 117657-74-6
• 化学式: C₁₅H₃₀OSSi₂
• 分子量: 314.64
• InChiKey: WIUQSCRQIAFXRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  dimethyl-propan-2-yl-(thiophen-3-ylmethoxy)silane 在 正丁基锂 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 为溶剂， 以40%的产率得到3-噻吩甲醇
  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 O→C silyl migrations of various 3-[(trialkylsilyl)oxymethyl]-furans and -thiophenes
  作者：Edward J. Bures、Brian A. Keay

  DOI：10.1016/s0040-4039(00)96838-2

  日期：1987.1
• BURES, EDWARD J.;KEAY, BRIAN A., TETRAHEDRON LETT., 28,(1987) N 48, 5965-5968
  作者：BURES, EDWARD J.、KEAY, BRIAN A.

  DOI：——

  日期：——