3-methyl-2-butenoyl fluoride | 55600-69-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: 3-methyl-2-butenoyl fluoride
• 英文别名: β-methyl crotonoyl fluoride；β,β-Dimethacryloylfluorid；3-methylbut-2-enoyl fluoride
• CAS: 55600-69-6
• 化学式: C₅H₇FO
• 分子量: 102.108
• InChiKey: ALNUUXBKZPSJEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-2-butenoyl fluoride 、 alkaline earth salt of/the/ methylsulfuric acid 生成 3,7-dimethylocta-3,6-diene-1-yne-5-one
  参考文献：
  名称：

  Two-step AdE reaction of dicobalthexacarbonyl complexes of conjugated enynes with independent variation in the nature of the electrophile and nucleophile

  摘要：

  DOI：

  10.1007/bf00948853
• 作为产物：
  描述：

  3-甲基巴豆酰氯 在 antimony fluoride 作用下， 生成 3-methyl-2-butenoyl fluoride
  参考文献：
  名称：

  Raman and infrared spectra, conformational stability, barriers to internal rotation and ab initio calculations for 3-methyl-2-butenoyl fluoride

  摘要：

  The Raman (3200 to 20 cm(-1)) spectra of liquid and solid and infrared (3200 to 400 cm(-1)) spectra of gaseous and solid 3-methyl-2-butenoyl fluoride (3,3-dimethylacryloyl fluoride), (CH3)(2)C=C(H)CFO, have been recorded. The far-infrared spectrum of the gas has also been recorded from 360 to 50 cm(-1) at a resolution of 0.1 cm(-1). The syn (s-cis) conformer is the only stable rotamer (two double bonds oriented cis to each other) present in the fluid at ambient temperature and solid states. The barriers for the syn (s-cis) to anti (s-trans) and anti to syn conformers are predicted to be 2498 and 1931 cm(-1), respectively, with an energy difference of 567 cm(-1) (1.62 kcal mol(-1)) from the RHF/631G* calculations. The energy difference was only slightly smaller, 487 cm(-1) (1.39 kcal mol(-1)) with electron correlation, i.e. MP2/6-31G*. Barriers to internal rotation of the two non-equivalent methyl rotors with torsional fundamentals at 205 (trans methyl rotor) and 109 cm(-1) were determined to be 920 cm(-1) (2.63 kcal mol(-1)) and 304 cm(-1) (0.87 kcal mol(-1)), respectively. A complete assignment of the normal vibrational modes is proposed. The structural parameters, force constants and vibrational frequencies for the syn conformer have been determined from ab initio gradient calculations employing the RHF/3-21G* and RHF/6-31G* basis sets along with electron correlation at the MP2/6-31G* level and the theoretical results are compared to the experimental values when appropriate. These results have been compared with the corresponding ones obtained for some similar molecules.

  DOI：

  10.1016/0022-2860(95)09210-2

文献信息

• STEREOSELECTIVE SYNTHESIS OF 1-<i>O</i>-ACYL-D-GLUCOPYRANOSE FROM 1-HYDROXY SUGAR AND ACYL FLUORIDES BY THE PROMOTION OF CESIUM FLUORIDE
  作者：Shin-ichiro Shoda、Teruaki Mukaiyama

  DOI：10.1246/cl.1982.861

  日期：1982.6.5

  In the presence of cesium fluoride, the reaction of 2,3,4,6-tetra-O-benzyl-d-glucopyranose with acyl fluorides affords the corresponding glucosyl esters in good yields under essentially neutral condition. The α⁄β ratio of produced glucosyl esters is greatly affected by reaction conditions and predominant formations of each anomer is achieved by procedures described herein.

  在氟化铯存在下，2,3,4,6-四-O-苄基-d-吡喃葡萄糖与酰氟反应在基本中性条件下以良好的产率提供相应的葡萄糖酯。所产生的葡萄糖酯的α/β比率很大程度上受反应条件影响，并且每种端基异构体的主要形成是通过本文描述的程序实现的。
• Spectral correlations for α, β-unsaturated acid halides
  作者：H.N. Al-Jallo、M.G. Jalhoom

  DOI：10.1016/0584-8539(75)80019-5

  日期：1975.3
• Two-step AdE reaction of dicobalthexacarbonyl complexes of conjugated enynes with independent variation in the nature of the electrophile and nucleophile
  作者：A. A. Shchegolev、W. A. Smit、G. S. Mikaelyan、A. S. Gybin、Yu. V. Kal'yan、M. Z. Krimer、R. Caple

  DOI：10.1007/bf00948853

  日期：1984.11
• Raman and infrared spectra, conformational stability, barriers to internal rotation and ab initio calculations for 3-methyl-2-butenoyl fluoride
  作者：J.R. Durig、Gamil A. Guirgis、Yanping Jin

  DOI：10.1016/0022-2860(95)09210-2

  日期：1996.6

  The Raman (3200 to 20 cm(-1)) spectra of liquid and solid and infrared (3200 to 400 cm(-1)) spectra of gaseous and solid 3-methyl-2-butenoyl fluoride (3,3-dimethylacryloyl fluoride), (CH3)(2)C=C(H)CFO, have been recorded. The far-infrared spectrum of the gas has also been recorded from 360 to 50 cm(-1) at a resolution of 0.1 cm(-1). The syn (s-cis) conformer is the only stable rotamer (two double bonds oriented cis to each other) present in the fluid at ambient temperature and solid states. The barriers for the syn (s-cis) to anti (s-trans) and anti to syn conformers are predicted to be 2498 and 1931 cm(-1), respectively, with an energy difference of 567 cm(-1) (1.62 kcal mol(-1)) from the RHF/631G* calculations. The energy difference was only slightly smaller, 487 cm(-1) (1.39 kcal mol(-1)) with electron correlation, i.e. MP2/6-31G*. Barriers to internal rotation of the two non-equivalent methyl rotors with torsional fundamentals at 205 (trans methyl rotor) and 109 cm(-1) were determined to be 920 cm(-1) (2.63 kcal mol(-1)) and 304 cm(-1) (0.87 kcal mol(-1)), respectively. A complete assignment of the normal vibrational modes is proposed. The structural parameters, force constants and vibrational frequencies for the syn conformer have been determined from ab initio gradient calculations employing the RHF/3-21G* and RHF/6-31G* basis sets along with electron correlation at the MP2/6-31G* level and the theoretical results are compared to the experimental values when appropriate. These results have been compared with the corresponding ones obtained for some similar molecules.