2,6-diphenyl-3,5-dimethyl-4H-pyran-4-one | 109614-24-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2,6-diphenyl-3,5-dimethyl-4H-pyran-4-one
• 英文别名: 3,5-Dimethyl-2,6-diphenylpyran-4-on；2,6-Diphenyl-3,5-dimethyltetrahydro-4-pyron；3,5-dimethyl-2,6-diphenyl-pyran-4-one；4H-Pyran-4-one, 3,5-dimethyl-2,6-diphenyl-；3,5-dimethyl-2,6-diphenylpyran-4-one
• CAS: 109614-24-6
• 化学式: C₁₉H₁₆O₂
• 分子量: 276.335
• InChiKey: GHICQRZIENHICV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-diphenyl-3,5-dimethyl-4H-pyran-4-one 在 N-溴代丁二酰亚胺(NBS) 、 邻苯二甲酸二丁酯 作用下， 以 四氯化碳 为溶剂， 反应 12.0h， 以60.5%的产率得到3,5-Bis(bromomethyl)-2,6-diphenylpyran-4-on
  参考文献：
  名称：

  Synthese und Konformationsanalyse von Pyranophanonen und Pyrylophanium-Verbindungen mit intraannularen Substituenten

  摘要：

  The synthesis of [3.3]dithiapyranophanone 6 and 11 is accomplished by use of the two-components-dilution-principle. Pyrolysis of their bis(sulfones) 7 and 12 gives the [2.2]pyranophanones 8, 9 and 13. Under preservation of conformation the intraannular carbonyl-function is used for the synthesis of methylpyranophanoles 14, 16 and 17. The synthesis of pyrylophanium compounds 15 and 18 is possible by elimination in trifluoroacetic acid.6 exhibits anti-conformation within its crystal-structure and like 7 reveals temperature-dependent behavior in solution. Using 6 as an example, a combination of C-13-NMR-spectroscopy, forcefield-calculation and computer-simulation is applied for the first time to give evidence for molecular-dynamic processes of cyclophanes.8 and 9 are the syn- and anti-conformers of the desired product, as shown by X-ray structural analysis. 13 reveals anti-conformation within its crystal structure as well as in solution. The conformational analysis of other new phanes described here is based on the H-1-NMR-spectra of these pyrolysis products.As expected the intraannular substituents of Pyrylophanium-lons 15 and 18 show the characteristic up-field-shift within their H-1-NMR-spectra.

  DOI：

  10.1002/prac.19933350603
• 作为产物：
  描述：

  2-甲基-1-苯基戊烷-1,3-二酮 在 硫酸 、 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 8.0h， 生成 2,6-diphenyl-3,5-dimethyl-4H-pyran-4-one
  参考文献：
  名称：

  Synthese und Konformationsanalyse von Pyranophanonen und Pyrylophanium-Verbindungen mit intraannularen Substituenten

  摘要：

  The synthesis of [3.3]dithiapyranophanone 6 and 11 is accomplished by use of the two-components-dilution-principle. Pyrolysis of their bis(sulfones) 7 and 12 gives the [2.2]pyranophanones 8, 9 and 13. Under preservation of conformation the intraannular carbonyl-function is used for the synthesis of methylpyranophanoles 14, 16 and 17. The synthesis of pyrylophanium compounds 15 and 18 is possible by elimination in trifluoroacetic acid.6 exhibits anti-conformation within its crystal-structure and like 7 reveals temperature-dependent behavior in solution. Using 6 as an example, a combination of C-13-NMR-spectroscopy, forcefield-calculation and computer-simulation is applied for the first time to give evidence for molecular-dynamic processes of cyclophanes.8 and 9 are the syn- and anti-conformers of the desired product, as shown by X-ray structural analysis. 13 reveals anti-conformation within its crystal structure as well as in solution. The conformational analysis of other new phanes described here is based on the H-1-NMR-spectra of these pyrolysis products.As expected the intraannular substituents of Pyrylophanium-lons 15 and 18 show the characteristic up-field-shift within their H-1-NMR-spectra.

  DOI：

  10.1002/prac.19933350603

文献信息

• v. Mikusch, Angewandte Chemie, 1959, vol. 71, p. 311
  作者：v. Mikusch

  DOI：——

  日期：——
• Zubkova, O. V.; Borodaev, S. V.; Luk'yanov, S. M., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 11.2, p. 2109 - 2111
  作者：Zubkova, O. V.、Borodaev, S. V.、Luk'yanov, S. M.

  DOI：——

  日期：——
• Synthese und Konformationsanalyse von Pyranophanonen und Pyrylophanium-Verbindungen mit intraannularen Substituenten
  作者：J�rgen Allwohn、Martin Brumm、Gernot Frenking、Matthias Hornivius、Werner Massa、Friedrich W. Steubert、Sigrid Wocadlo

  DOI：10.1002/prac.19933350603

  日期：——

  The synthesis of [3.3]dithiapyranophanone 6 and 11 is accomplished by use of the two-components-dilution-principle. Pyrolysis of their bis(sulfones) 7 and 12 gives the [2.2]pyranophanones 8, 9 and 13. Under preservation of conformation the intraannular carbonyl-function is used for the synthesis of methylpyranophanoles 14, 16 and 17. The synthesis of pyrylophanium compounds 15 and 18 is possible by elimination in trifluoroacetic acid.6 exhibits anti-conformation within its crystal-structure and like 7 reveals temperature-dependent behavior in solution. Using 6 as an example, a combination of C-13-NMR-spectroscopy, forcefield-calculation and computer-simulation is applied for the first time to give evidence for molecular-dynamic processes of cyclophanes.8 and 9 are the syn- and anti-conformers of the desired product, as shown by X-ray structural analysis. 13 reveals anti-conformation within its crystal structure as well as in solution. The conformational analysis of other new phanes described here is based on the H-1-NMR-spectra of these pyrolysis products.As expected the intraannular substituents of Pyrylophanium-lons 15 and 18 show the characteristic up-field-shift within their H-1-NMR-spectra.