[(1S,3S,4S,6R)-4-hydroxy-4,7,7-trimethyl-3-bicyclo[4.1.0]heptanyl] acetate | 28435-84-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [(1S,3S,4S,6R)-4-hydroxy-4,7,7-trimethyl-3-bicyclo[4.1.0]heptanyl] acetate
• CAS: 28435-84-9
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.28
• InChiKey: ULLVLQDHBOHWGJ-WYFGTUCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-蒈烯 在 吡啶 、 硫酸 、 双氧水 作用下， 以 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 9.5h， 生成 [(1S,3S,4S,6R)-4-hydroxy-4,7,7-trimethyl-3-bicyclo[4.1.0]heptanyl] acetate 、 (1S,3R,4R,6R)-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diyl diacetate
  参考文献：
  名称：

  Carane‐3,4‐diol Derivatives as Potential Water‐Based Herbicides

  摘要：

  Twelve novel carane‐3,4‐diol derivatives were designed, synthesized, and evaluated for their herbicidal activities against Lolium multiflorum Lam. and Brassica campestris for the first time. The relationships between the chemical structural factors, including types, the number or the carbon chain length of functional groups, associated with the lipophilicity and the herbicidal activity of the tested compounds were also discussed. The results showed that most of newly synthesized compounds had a dose‐dependent, herbicidal activity against the root and shoot growths of Lolium multiflorum Lam. and Brassica campestris. Compared to carane‐3,4‐diol, most of the target derivatives possessed improved lipophilicity and certain solubilities in representative solvents with different polarities. Particularly, ester derivatives 3a‐3b and 3e can be dissolved or dispersed in water, but also displayed higher herbicidal activity against Lolium multiflorum Lam. and Brassica campestris than other ester derivatives. The 50% inhibitory concentration (IC50) value of compound 3e against shoot growth of Brassica campestris (0.485 mmol/L) was superior to that of commercial herbicide glyphosate (1.14 mmol/L), indicating that the potential application as a water‐based herbicide for Brassica campestris control.

  DOI：

  10.1002/cbdv.202301867