2-epikadsurenone | 104832-98-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 2-epikadsurenone
• 英文别名: (inverted exclamation markA)-7-epi-Kadsurenone；(2R,3R,3aS)-2-(3,4-dimethoxyphenyl)-3a-methoxy-3-methyl-5-prop-2-enyl-2,3-dihydro-1-benzofuran-6-one
• CAS: 104832-98-6
• 化学式: C₂₁H₂₄O₅
• 分子量: 356.419
• InChiKey: VDYACOATPFOZIO-PZVFOTJXSA-N

物化性质

• 沸点：
  491.1±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  海风藤酮 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 2-epikadsurenone
  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

文献信息

• Biomimetic synthesis of the neolignans kadsurenone, denudatin B, O-methyl-liliflodione, and liliflol B
  作者：David A. Horne、Kenichi Yakushijin、George Büchi

  DOI：10.1016/s0040-4039(99)01063-1

  日期：1999.7

  Synthesis of (+/-)-kadsurenone (1), (+/-)-denudatin B (2), (+/-)-O-methyl-liliflodione (3a), and (+/-)-liliflol B (14) is described. The key synthetic step is a biomimetic cationic cycloaddition between E- or Z-1,2-dimethoxy-4-propenylbenzene (11) and ortho-quinone monoketal 10. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Structure-activity relationships of kadsurenone analogues
  作者：Mitree M. Ponpipom、Robert L. Bugianesi、David R. Brooker、Bao-zhen Yue、San-bao Hwang、Tsung-ying Shen

  DOI：10.1021/jm00384a023

  日期：1987.1

  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.