2-acetylpholoroglucinol 1,3-bis(benzyl ether) | 76799-38-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetylpholoroglucinol 1,3-bis(benzyl ether)
• 英文别名: 2,6-bis(benzyloxy)-4-hydroxyacetophenone；1-[4-Hydroxy-2,6-bis(phenylmethoxy)phenyl]ethanone
• CAS: 76799-38-7
• 化学式: C₂₂H₂₀O₄
• 分子量: 348.398
• InChiKey: FDUUSWOCQTYEAO-UHFFFAOYSA-N

物化性质

• 沸点：
  559.0±45.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-acetylpholoroglucinol 1,3-bis(benzyl ether) 在 氢氧化钾 、 硫酸 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 150.0h， 生成 2,3',6-tris(benzyloxy)-4-<1-(carbo-tert-butoxy)-3,4-dihydroxybutoxy>-4'-propoxychalcone
  参考文献：
  名称：

  Dihydrochalcone sweeteners. A study of the atypical temporal phenomena

  摘要：

  Neohesperidin dihydrochalcone (NHDHC), known since 1963 as an intensely sweet compound, is determined to be 340 +/- 60 (p less than 0.05) times more potent than sucrose. The unusual temporal properties of this material are hypothesized as being due to the effects of metabolism, conformation, chelation, or hydrophobicity. Forty-four analogues are synthesized to test the four hypotheses, none of which are strongly supported. A method of quantitation of temporal characteristics of tastant molecules is developed so as to allow comparison of taste appearance time (AT) and extinction time (ET) of experimental compounds. Four of the new compounds, 40 and 43-45, exhibit high sweetness potencies, ranging from 280 and 440 times sucrose, and may be useful in selected food systems. The temporal taste characteristics remain unimproved over NHDHC, however.

  DOI：

  10.1021/jm00136a011
• 作为产物：
  描述：

  Phloroacetophenone 4'-O-β-neohesperidoside 在 硫酸 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 2-acetylpholoroglucinol 1,3-bis(benzyl ether)
  参考文献：
  名称：

  Dihydrochalcone sweeteners. A study of the atypical temporal phenomena

  摘要：

  Neohesperidin dihydrochalcone (NHDHC), known since 1963 as an intensely sweet compound, is determined to be 340 +/- 60 (p less than 0.05) times more potent than sucrose. The unusual temporal properties of this material are hypothesized as being due to the effects of metabolism, conformation, chelation, or hydrophobicity. Forty-four analogues are synthesized to test the four hypotheses, none of which are strongly supported. A method of quantitation of temporal characteristics of tastant molecules is developed so as to allow comparison of taste appearance time (AT) and extinction time (ET) of experimental compounds. Four of the new compounds, 40 and 43-45, exhibit high sweetness potencies, ranging from 280 and 440 times sucrose, and may be useful in selected food systems. The temporal taste characteristics remain unimproved over NHDHC, however.

  DOI：

  10.1021/jm00136a011

文献信息

• Practical Synthesis of a<i>C</i>-Glycosyl Flavonoid via<i>O</i>→<i>C</i>Glycoside Rearrangement
  作者：Toshihiro Kumazawa、Kazuhito Ohki、Mitsuo Ishida、Shingo Sato、Jun-ichi Onodera、Shigeru Matsuba

  DOI：10.1246/bcsj.68.1379

  日期：1995.5

  The C-glycosylation of 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride and 2-acetylphloroglucinol 3,5-bis(alkyl ether) in the presence of boron trifluoride etherate as an activator stereoselectively gave the β-C-glucoside in a good yield via O → C glycoside rearrangement. Subsequently, aldol condensation of the C-glucoside with benzaldehyde afforded the corresponding β-C-glucosyl chalcone in a good

  2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖基氟和2-乙酰间苯三酚3,5-双（烷基醚）在三氟化硼醚化物作为活化剂存在下的C-糖基化立体选择性地得到通过 O → C 糖苷重排，β-C-糖苷的产率很高。随后，C-葡萄糖苷与苯甲醛的羟醛缩合以良好的收率提供相应的β-C-葡萄糖基查耳酮。