guai-2-en-10α-methanol | 1228963-25-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: guai-2-en-10α-methanol
• 英文别名: [(1S,3aS,4R,8S,8aR)-8-ethyl-1,4-dimethyl-3a,5,6,7,8,8a-hexahydro-1H-azulen-4-yl]methanol
• CAS: 1228963-25-4
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: HHMZGTLMFPVSNL-YTFOTSKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  guai-2-en-10α-methanol 、 乙酸酐 在 吡啶 作用下， 反应 24.0h， 以13.6 mg的产率得到guai-2-en-10α-methyl methanoate
  参考文献：
  名称：

  Guaiane sesquiterpenes from seaweed Ulva fasciata Delile and their antibacterial properties

  摘要：

  Two new guaiane sesquiterpene derivatives, guai-2-en-10 alpha-ol (1) and guai-2-en-10 alpha-methanol (2), were chromatographically purified as major constituents of the CHCl(3)/CH(3)OH (1.1, v/v) soluble fraction of Ulva fasciata. Acetylation of 2 furnished guai-2-en-10 alpha-methyl methanoate (3) with acetyl group at CH position. The structures of the compounds were elucidated using one and two-dimensional NMR and mass spectrometric analysis. Compounds 2 and 3 exhibited significant inhibition to the growth of Vibrio parahaemolyticus with minimum inhibitory concentrations of 25 and 35 mu g/mL, respectively. The electronegative C10 acetyl group with high polarisability (7.02 x 10(-24) cm(3)) in 3 appeared to withdraw electron cloud from substituted cycloheptyl ring and (R)-3-methylcyclohept-1-ene moiety, thus acting as the nucleophilic center of the molecule resulting in high bioactivity.

  DOI：

  10.1016/j.ejmech.2010.01.065