2,3,4,5-Tetrafluoro-1-methoxycyclopenta-2,4-dien-1-ol | 131152-55-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,5-Tetrafluoro-1-methoxycyclopenta-2,4-dien-1-ol
• CAS: 131152-55-1
• 化学式: C₆H₄F₄O₂
• 分子量: 184.09
• InChiKey: YDOSMTZYVNHBCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4,5-Tetrafluoro-1-methoxycyclopenta-2,4-dien-1-ol 、 重氮甲烷 生成 1,2,3,4-Tetrafluoro-5,5-dimethoxycyclopenta-1,3-diene
  参考文献：
  名称：

  LEMAL, DAVID M.;KLOPOTEK, DAVID L.;WILTERDINK, JANET L.;SAUNDERS, W. DANI+, J. ORG. CHEM., 56,(1991) N, C. 157-160

  摘要：

  DOI：
• 作为产物：
  描述：

  tetrafluoro-cyclobut-3-ene-1,2-dicarboxylic acid anhydride 在 sodium methylate 作用下， -78.0~585.0 ℃ 、133.32 Pa 条件下， 生成 2,3,4,5-Tetrafluoro-1-methoxycyclopenta-2,4-dien-1-ol
  参考文献：
  名称：

  Carbonyl chemistry of tetrafluorocyclopentadienone

  摘要：

  In order to control the Diels-Alder reactivity of the very labile title compound 1, experiments designed to modify the carbonyl group have been carried out. With methanol a hemiketal (4) is formed reversibly at low temperatures, but conjugate addition to give 3-methoxy derivatives 5 and 6 occurs at ordinary temperatures. Diazomethane reacts with 1 in cold methanol to give a spirooxirane (9) which undergoes Diels-Alder dimerization orders of magnitude slower than dienone 1 at room temperature. Hydrogen cyanide gives a cyanohydrin (15) with 1 at low temperatures, but the compound decomposes at 0-degrees-C. Trimethylsilyl cyanide yields the trimethylsilyl cyanohydrin 16, a stable derivative of 1 that dimerizes only at elevated temperatures, yet retains reactivity as a Diels-Alder diene.

  DOI：

  10.1021/jo00001a032