4-(ethoxycarbonyl)-5,5-dimethyl-3-oxocyclohex-1-en-1-yl benzoate

• 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: 4-(ethoxycarbonyl)-5,5-dimethyl-3-oxocyclohex-1-en-1-yl benzoate
• 英文别名: Ethyl 4-benzoyloxy-6,6-dimethyl-2-oxocyclohex-3-ene-1-carboxylate；ethyl 4-benzoyloxy-6,6-dimethyl-2-oxocyclohex-3-ene-1-carboxylate
• 化学式: C₁₈H₂₀O₅
• 分子量: 316.354
• InChiKey: XOLCNCPHJYRIOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5,5-dimethyl-3-oxocyclohex-1-en-1-yl benzoate 、 氰基甲酸乙酯 在 lithium hexamethyldisilazane 、 N,N-二甲基丙烯基脲 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以80%的产率得到4-(ethoxycarbonyl)-5,5-dimethyl-3-oxocyclohex-1-en-1-yl benzoate
  参考文献：
  名称：

  Kava analogues as agents for treatment of periodontal diseases: Synthesis and initial biological evaluation

  摘要：

  Six kava analogues of the structural type 3-oxocyclohex-1-en-1-yl benzoates (and corresponding benzamides) were synthesized and evaluated for their affect on periodontal deconstruction in collagen anti-body primed oral gavage model of periodontitis. The compounds were prepared through an acylation or amidation of the enolizable cyclic 1,3-diketone. We have learned that three of the analogues are responsible for the reduction of inflammatory cell counts within soft tissue. These novel kava-like molecules where the lactone is replaced by an alpha,beta-unsaturated ketone show promise in the prevention and treatment of inflammation and alveolar bone loss associated with periodontitis.

  DOI：

  10.1016/j.bmcl.2018.05.026

文献信息

• Kava analogues as agents for treatment of periodontal diseases: Synthesis and initial biological evaluation
  作者：Bin Cai、James S. Panek、Salomon Amar

  DOI：10.1016/j.bmcl.2018.05.026

  日期：2018.9

  Six kava analogues of the structural type 3-oxocyclohex-1-en-1-yl benzoates (and corresponding benzamides) were synthesized and evaluated for their affect on periodontal deconstruction in collagen anti-body primed oral gavage model of periodontitis. The compounds were prepared through an acylation or amidation of the enolizable cyclic 1,3-diketone. We have learned that three of the analogues are responsible for the reduction of inflammatory cell counts within soft tissue. These novel kava-like molecules where the lactone is replaced by an alpha,beta-unsaturated ketone show promise in the prevention and treatment of inflammation and alveolar bone loss associated with periodontitis.