Difluorocyclopropenone | 61486-72-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: Difluorocyclopropenone
• 英文别名: 2,3-Difluorocycloprop-2-en-1-one
• CAS: 61486-72-4
• 化学式: C₃F₂O
• 分子量: 90.0292
• InChiKey: RXKJNYIJXREFHQ-UHFFFAOYSA-N

物化性质

• 沸点：
  93.0±40.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Difluorocyclopropenone 生成 1,2-二氟乙炔
  参考文献：
  名称：

  BRAHMS, JOHN C.;DAILEY, WILLIAM P., J. AMER. CHEM. SOC., 111,(1989) N4, C. 8940-8941

  摘要：

  DOI：
• 作为产物：
  描述：

  二氟马来酸酐 反应 1.0h， 生成 Difluorocyclopropenone
  参考文献：
  名称：

  二氟马来酸酐作为基质分离的二氟丙二烯酮、二氟环丙烯酮和二氟乙炔的来源

  摘要：

  A 240 nm，反应 de la difluoro-3,4 dihydro-2,5 furannedione-2,5。获得 de la difluoro-2,3 cyclopropenone, du difluoroacetylene et de la difluoro-3,3 propanedienone

  DOI：

  10.1021/ja00206a039

文献信息

• Why Is the Diels-Alder Adduct between Difluorocyclopropenone and 1,3-Diphenylisobenzofuran So Reactive? An ab Initio Molecular Orbital Study of the Ring Opening of cis-2,3-Difluorocyclopropanone
  作者：Carolyn A. Jacobs、William P. Dailey

  DOI：10.1021/jo00129a013

  日期：1995.12

  Reaction of difluorocyclopropenone (5) and diphenylisobenzofuran (2) yields the two isomeric 1:2 cycloadducts 7 and 8 in a ratio of 9:1. The structure of the major isomer was determined by X-ray crystallography and was shown to be the unsymmetrical one. The minor isomer is assigned a symmetrical structure based on spectroscopic data. Attempts to observe the initial 1:1 Diels-Alder adduct 6 were unsuccessful because of the low reactivity of difluorocyclopropenone and the high reactivity of the presumed intermediate difluorocyclopropanone 6. As an aid in the investigation, ab initio calculations were carried out on the ring-opening reaction of the parent cis-2,3-difluorocyclopropanone (11) to the corresponding oxyallyl species 13. The results are compared with previous theoretical and experimental work. cis-2,3-difluorocyclopropanone is calculated to have a much smaller barrier (12-14 kcal/mol) to ring opening than the parent cyclopropanone (22-28 kcal/mol).
• Synthesis, microwave spectrum, and ab initio calculations for difluorocyclopropenone
  作者：Carolyn A. Jacobs、John C. Brahms、William P. Dailey、Kyle Beran、Marlin D. Harmony

  DOI：10.1021/ja00027a016

  日期：1992.1

  Difluorocyclopropenone was prepared by gas-phase photolysis of difluoromaleic anhydride and was characterized spectroscopically. It is unstable at room temperature but may be stored for long periods of time at -78-degrees-C. Microwave spectra of the normal and O-18 isotopomer for difluorocyclopropenone were measured. The structural parameters were determined to be r(C1O) = 1.192 angstrom, r(C1C2) = 1.453 angstrom, r(C2C3) = 1.324 angstrom, and r(CF) = 1.314 angstrom, and the electric dipole moment was found to be 2.32 D. Ab initio calculations at the CISD/6-31G* level are reported for cyclopropenone, difluorocyclopropenone, and related cyclopropenes and are in good agreement with the experimental results. The experimental geometry and ab initio computations indicate that difluorocyclopropenone enjoys a resonance energy comparable to that of the parent compound.