3,5-Bis(bromomethyl)-2,6-diphenylpyran-4-on | 153903-85-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3,5-Bis(bromomethyl)-2,6-diphenylpyran-4-on
• 英文别名: 3,5-bis(bromomethyl)-2,6-diphenyl-4H-pyran-4-one；3,5-Bis(bromomethyl)-2,6-diphenyl-4H-pyran-4-one；3,5-bis(bromomethyl)-2,6-diphenylpyran-4-one
• CAS: 153903-85-6
• 化学式: C₁₉H₁₄Br₂O₂
• 分子量: 434.127
• InChiKey: PCNXWTXETZXIAZ-UHFFFAOYSA-N

物化性质

• 沸点：
  549.8±50.0 °C(Predicted)
• 密度：
  1.611±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  4
• 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：

  3,5-Bis(bromomethyl)-2,6-diphenylpyran-4-on 在 一水合肼 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 3,5-di(aminoxy)-2,6-diphenyl-4H-pyran-4-one
  参考文献：
  名称：

  4H-吡喃-4-酮醛肟衍生物的合成

  摘要：

  4H-pyran-4-ones 4-7a,b 的醛肟衍生物已通过二（氨氧基甲基）吡喃酮 3a,b 与芳香醛的反应合成。

  DOI：

  10.3390/70200239
• 作为产物：
  描述：

  2-甲基-1-苯基戊烷-1,3-二酮 在 N-溴代丁二酰亚胺(NBS) 、 邻苯二甲酸二丁酯 、 硫酸 、 sodium hydride 作用下， 以 四氯化碳 、 乙二醇二甲醚 为溶剂， 反应 20.0h， 生成 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

文献信息

• Chemistry of Pyrones, Part 3: New Podands of 4H-Pyran-4-ones
  作者：Aziz Shahrisa、Alireza Banaei

  DOI：10.3390/50300200

  日期：——

  New derivatives of 3,5-disubstituted 4H-Pyran-4-one podands (9-15) were prepared by transesterification reaction of dimethyl or diethyl 2,6-dimethyl-4H-pyran-4-one-3,5-dicarboxylate with some glycol, glycol ethers or by nucleophilic substitution of some phenols or glycol ethers with 3,5-bis (bromomethyl)-2,6-diphenyl-4H-pyran-4-one.

  新型的3,5-二取代的4H-吡営-4-酮穴醚衍生物（9-15）通过二甲基或二乙基2,6-二甲基-4H-吡喃-4-酮-3,5-二羧酸酯与某些多元醇、多元醇醚的酯交换反应，或者通过某些酚或多元醇醚与3,5-双（溴甲基）-2,6-二苯基-4H-吡喃-4-酮的亲核取代反应制备得到。
• Chemistry of Pyrones, Part 5: New Crown Ether and Podand Derivatives of 3,5-Bis(bromomethyl)-2,6-diphenyl-4H-pyran-4-one
  作者：Aziz Shahrisa、Alireza Banaei

  DOI：10.3390/60900721

  日期：——

  New podand and crown ether derivatives of 3,5-disubstituted 4H-pyran-4-one (8-11) were prepared by the nucleophilic substitution reaction of 3,5-bis(bromomethyl)-2,6-diphenyl-4H-pyran-4-one with o-nitrophenol, 8-hydroxyquinoline, 2-hydroxymethyl pyridine and triethyleneglycol, respectively. The yield of 3,5-bis[(2-formylphenoxy) methyl]-2,6-diphenyl-4H-pyran-4-one has been improved by modification of our previous method using NaOH instead of Et3N.

  通过 3,5-双（溴甲基）-2,6-二苯基-4H-吡喃-4-酮分别与邻硝基苯酚、8-羟基喹啉、2-羟甲基吡啶和三乙二醇的亲核取代反应，制备了新的 3,5-二取代 4H-吡喃-4-酮的荚兰和冠醚衍生物（8-11）。通过使用 NaOH 代替 Et3N 来改进我们以前的方法，3,5-双[(2-甲酰基苯氧基)甲基]-2,6-二苯基-4H-吡喃-4-酮的产率得到了提高。
• 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.
• Synthesis of Some Aldoxime Derivatives of 4H-Pyran-4-ones
  作者：Fateme Abrishami、Reza Teimuri-Mofrad、Yadollah Bayat、Aziz Shahrisa

  DOI：10.3390/70200239

  日期：——

  Aldoxime derivatives of 4H-pyran-4-ones 4-7a,b have been synthesized by the reaction of di(aminoxymethyl) pyranones 3a,b with aromatic aldehydes.

  4H-pyran-4-ones 4-7a,b 的醛肟衍生物已通过二（氨氧基甲基）吡喃酮 3a,b 与芳香醛的反应合成。