[4-[(Z)-3-acetyloxybut-2-enyl]phenyl] acetate | 184953-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: [4-[(Z)-3-acetyloxybut-2-enyl]phenyl] acetate
• CAS: 184953-87-5
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: HOVCJZJSPXQUOI-WMZJFQQLSA-N

物化性质

• 沸点：
  363.4±35.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [4-[(Z)-3-acetyloxybut-2-enyl]phenyl] acetate 在 platinum(IV) oxide sodium hydroxide 、 氘 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 4-[(2S,3R)-2,3-dideuterio-3-hydroxybutyl]phenol
  参考文献：
  名称：

  Stereochemistry of the Baeyer−Villiger-Type Conversion of 4-(4-Hydroxyphenyl)butan-2-one (Raspberry Ketone) into Tyrosol Mediated by Beauveria bassiana

  摘要：

  Feeding experiments in Beauveria bassiana (ATCC 7159) of (2R,3S)-[2,3-H-2(2)]-4-(4-hydroxyphenyl)-butan-2-ol (15) and (2R,3R)-[1,3-H-2(4)]-(4-hydroxyphenyl)-butan-2-ol (16) afford (1S)- and (IR)-[1-H-2]tyrosol (17) and (18), respectively, as indicated by NMR studies on the (+)-MTPA esters 21 and 23 and comparison with an authentic sample of the (S) enantiomer. These results indicate that the C-2, Baeyer-Villiger-type, chain shortening of the C-6-C-4 framework of the intermediate raspberry ketone 1 to give the C-6-C-2 tyrosol (4) occurs with retention of configuration. The asymmetrically labeled substrates 15 and 16 have been obtained by enzymic resolution of derivatives of (2SR,3RS)-6 and (2SR,3SR)-12, prepared, in turn, by syn catalytic reduction with deuterium and with hydrogen gas, respectively, of the (Z) enol acetates 5 and 11.

  DOI：

  10.1021/jo9614553
• 作为产物：
  描述：

  乙酸酐 、 覆盆子酮 在 高氯酸 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 [4-[(Z)-3-acetyloxybut-2-enyl]phenyl] acetate 、
  参考文献：
  名称：

  Stereochemistry of the Baeyer−Villiger-Type Conversion of 4-(4-Hydroxyphenyl)butan-2-one (Raspberry Ketone) into Tyrosol Mediated by Beauveria bassiana

  摘要：

  Feeding experiments in Beauveria bassiana (ATCC 7159) of (2R,3S)-[2,3-H-2(2)]-4-(4-hydroxyphenyl)-butan-2-ol (15) and (2R,3R)-[1,3-H-2(4)]-(4-hydroxyphenyl)-butan-2-ol (16) afford (1S)- and (IR)-[1-H-2]tyrosol (17) and (18), respectively, as indicated by NMR studies on the (+)-MTPA esters 21 and 23 and comparison with an authentic sample of the (S) enantiomer. These results indicate that the C-2, Baeyer-Villiger-type, chain shortening of the C-6-C-4 framework of the intermediate raspberry ketone 1 to give the C-6-C-2 tyrosol (4) occurs with retention of configuration. The asymmetrically labeled substrates 15 and 16 have been obtained by enzymic resolution of derivatives of (2SR,3RS)-6 and (2SR,3SR)-12, prepared, in turn, by syn catalytic reduction with deuterium and with hydrogen gas, respectively, of the (Z) enol acetates 5 and 11.

  DOI：

  10.1021/jo9614553