carabrol | 68776-20-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: carabrol
• 英文别名: (3aR,4aS,5S,5aR,6aR)-5-(3-hydroxybutyl)-5a-methyl-3-methylidene-3a,4,4a,5,6,6a-hexahydrocyclopropa[f][1]benzofuran-2-one
• CAS: 68776-20-5
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: MTIXBBDFRVGBOQ-WQFFSLPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  carabrol 在 chromium(VI) oxide 、 硫酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78 mg的产率得到天名精内酯酮
  参考文献：
  名称：

  Sesquiterpene lactones from Carpesium abrotanoides

  摘要：

  DOI：

  10.1016/s0031-9422(00)97693-3
• 作为产物：
  描述：

  天名精内酯酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 carabrol
  参考文献：
  名称：

  Synthesis and Antifungal Activity of Carabrone Derivatives

  摘要：

  利用孢子萌发法合成了卡拉布酮（1）的九种衍生物 6-14 并对 Colletotrichum lagenarium Ell et Halst 进行了体外测试。结构-活性关系（SAR）表明，γ-内酯是 1 的抗真菌活性所必需的，而 1 的 C-4 位上的取代基会显著影响其抗真菌活性。

  DOI：

  10.3390/molecules15096485

文献信息

• Synthesis and Antifungal Activities of Carabrol Ester Derivatives
  作者：Jun-Tao Feng、Hao Wang、Shuang-Xi Ren、Jun He、Yong Liu、Xing Zhang

  DOI：10.1021/jf205123d

  日期：2012.4.18

  Thirty-eight new ester derivatives of carabrol were designed, synthesized, and characterized by H-1 and C-13 NMR and HR-ESI-MS. Their antifungal activities against the fungal pathogen Colletotrichum lagenarium were evaluated using a spore germination assay. Of these 38 ester derivatives, 16 showed higher antifungal activity than that of carabrol and 7 showed higher antifungal activity than that of carabrone. It was found that the C-4 position of carabrol was a key position involving its antifungal activity, which showed the variation of 50% inhibition concentration (IC50) from 2.70 to 52.33 mu g/mL. When substituted by the phenyl ring, the ester derivatives with electron-attracting groups showed higher activity than those with electron-donating ones. Two ester derivatives, carabryl 4-cynaobenzoate (II-17, IC50 2.70 mu g/mL) and carabryl 4-isopropylbenzoate (II-27, IC50 2.82 mu g/mL), showed only slightly lower antifungal activity than that of the positive control chlorothalonil (IC50 0.87 mu g/mL) and have been identified as promising leads for development of new environmentally friendly fungicides.