(4R,5S)-2,3,4,5-tetrafluoro-4-methoxycyclopent-2-en-1-one | 131152-56-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5S)-2,3,4,5-tetrafluoro-4-methoxycyclopent-2-en-1-one
• CAS: 131152-56-2；131152-57-3
• 化学式: C₆H₄F₄O₂
• 分子量: 184.09
• InChiKey: JCHQFGUBGSBGDR-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  tetrafluoro-cyclobut-3-ene-1,2-dicarboxylic acid anhydride 在 methanolate 、 sodium methylate 作用下， -78.0~585.0 ℃ 、133.32 Pa 条件下， 生成 (4R,5S)-2,3,4,5-tetrafluoro-4-methoxycyclopent-2-en-1-one
  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

文献信息

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

  DOI：——

  日期：——