rac-(2S,3S)-6-hydroxy-2-(3,4-dimethoxyphenyl)-3-methyl-2,3-dihydrobenzofuran | 104761-78-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: rac-(2S,3S)-6-hydroxy-2-(3,4-dimethoxyphenyl)-3-methyl-2,3-dihydrobenzofuran
• CAS: 104761-78-6
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: LQUPAOYBIPPZFR-BTDLBPIBSA-N

物化性质

• 沸点：
  410.3±45.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 rac-(2S,3S)-6-hydroxy-2-(3,4-dimethoxyphenyl)-3-methyl-2,3-dihydrobenzofuran 在 lead(IV) acetate 作用下， 反应 0.5h， 以61%的产率得到(2R,3S,3aS)-2-(3,4-Dimethoxy-phenyl)-3a-methoxy-3-methyl-3,3a-dihydro-2H-benzofuran-6-one
  参考文献：
  名称：

  Structure-activity relationships of kadsurenone analogues

  摘要：

  Kadsurenone, a specific receptor antagonist of platelet-activating factor (PAF), and its analogues were prepared from derivatives of cinnamyl alcohol and (allyloxy)phenol. Racemic kadsurenone, resolvable by a Chiralpak column at low temperatures, has an IC50 value of 2 X 10(-7) M, which is about 50% of the activity of the natural product (IC50 = 1 X 10(-7) M). The structural specificity of kadsurenone was further demonstrated by the low PAF-receptor-blocking activities of denudatin B, mirandin A, desallylkadsurenone, and the 2-epimer of kadsurenone.

  DOI：

  10.1021/jm00384a023
• 作为产物：
  描述：

  (E)-3-(3,4-二甲氧基苯基)烯丙醇 在 palladium on activated charcoal 氢气 、 三苯基膦 、 N,N-二乙基苯胺 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 7.0h， 生成 rac-(2S,3S)-6-hydroxy-2-(3,4-dimethoxyphenyl)-3-methyl-2,3-dihydrobenzofuran
  参考文献：
  名称：

  Structure-activity relationships of kadsurenone analogues

  摘要：

  Kadsurenone, a specific receptor antagonist of platelet-activating factor (PAF), and its analogues were prepared from derivatives of cinnamyl alcohol and (allyloxy)phenol. Racemic kadsurenone, resolvable by a Chiralpak column at low temperatures, has an IC50 value of 2 X 10(-7) M, which is about 50% of the activity of the natural product (IC50 = 1 X 10(-7) M). The structural specificity of kadsurenone was further demonstrated by the low PAF-receptor-blocking activities of denudatin B, mirandin A, desallylkadsurenone, and the 2-epimer of kadsurenone.

  DOI：

  10.1021/jm00384a023