3,4,5-trimethoxycinnamyl 3-(allyloxy)phenyl ether | 104761-74-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,4,5-trimethoxycinnamyl 3-(allyloxy)phenyl ether
• 英文别名: 1,2,3-trimethoxy-5-[(E)-3-(3-prop-2-enoxyphenoxy)prop-1-enyl]benzene
• CAS: 104761-74-2
• 化学式: C₂₁H₂₄O₅
• 分子量: 356.419
• InChiKey: ZTILSUZWQSYWHL-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  26.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3,4,5-trimethoxycinnamyl 3-(allyloxy)phenyl ether 在 N,N-二乙基苯胺 作用下， 反应 13.0h， 以24%的产率得到Rac-(2S,3S)-5-allyl-6-hydroxy-2-(3,4,5-trimethoxyphenyl)-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
• 作为产物：
  描述：

  3,4,5-三甲氧基肉桂酸 在 lithium aluminium tetrahydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3,4,5-trimethoxycinnamyl 3-(allyloxy)phenyl ether
  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