(5Z)-3-benzyl-5-[(2,5-dimethoxyphenyl)methylidene]furan-2-one | 887645-73-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5Z)-3-benzyl-5-[(2,5-dimethoxyphenyl)methylidene]furan-2-one
• CAS: 887645-73-0
• 化学式: C₂₀H₁₈O₄
• 分子量: 322.361
• InChiKey: CDHLGDYYUMEABO-PDGQHHTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 生成 (5Z)-3-benzyl-5-[(2,5-dimethoxyphenyl)methylidene]furan-2-one
  参考文献：
  名称：

  Synthesis of Photosynthesis-Inhibiting Nostoclide Analogues

  摘要：

  A series of 34 3-benzyl-5-(arylmethylene)furan-2(5H)-ones, designed using the naturally occurring toxins nostoclides as a lead structure, was synthesized as potential inhibitors of the photosynthetic electron transport. All compounds were fully characterized by IR, NMR (H-1 and C-13), and MS spectrometry. HMBC and HSQC bidimensional experiments allowed 13 C and H-1 assignments. Their biological activities were evaluated in vitro as the ability to interfere with light-driven reduction of ferricyanide by isolated spinach chloroplasts. About two-thirds of the compounds exhibited inhibitory properties in the micromolar range against the basal electron flow from water to K-3[Fe(CN)(6)]. The inhibitory potential of these 3-benzyl-5-(aryl methylene)furan-2(5H)-one lactones is higher than that of other nostoclide analogues previously synthesized in the same laboratories.

  DOI：

  10.1021/jf072964g