5,5-dimethyl-3-oxocyclohex-1-en-1-yl benzoate | 68197-30-8

• 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: 5,5-dimethyl-3-oxocyclohex-1-en-1-yl benzoate
• 英文别名: 3-benzoyloxy-5,5-dimethyl-2-cyclohexen-1-one；3-Benzoyloxy-5,5-dimethyl-cyclohex-2-enon；3-Benzoyloxy-5,5-dimethyl-2-cyclohexenon；(5,5-dimethyl-3-oxocyclohexen-1-yl) benzoate
• CAS: 68197-30-8
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: KXJJJCPKLBPFJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,5-dimethyl-3-oxocyclohex-1-en-1-yl benzoate 在 potassium cyanide 、 三乙胺 作用下， 以 乙腈 为溶剂， 生成 2-苯甲酰基-5,5-二甲基-1,3-环己二酮
  参考文献：
  名称：

  N-烷基-3-取代四氢吲唑酮的正交区域选择性合成

  摘要：

  从 Boc 保护的烷基肼 1 中实现了区域选择性和正交合成 N-烷基-3-取代四氢吲唑酮 3 和 4 的互补区域异构体的不同策略。通过合成 3 和 4 验证了该方法的稳健性和底物通用性1 分别与各种 2-酰基环己烷-1,3-二酮 2 和醛的分子内和分子间缩合。

  DOI：

  10.1002/ejoc.201000516
• 作为产物：
  描述：

  苯甲酰氯 、 5,5-二甲基-1,3-环己二酮 在 吡啶 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 以95%的产率得到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

• A New Simple Synthesis of 2-Acylcyclohexane-1,3-diones
  作者：A. A. AKHREM、F. A. LAKHVICH、S. I. BUDAI、T. S. KHLEBNICOVA、I. I. PETRUSEVICH

  DOI：10.1055/s-1978-24943

  日期：——
• Akhrem, A. A.; Borisov, E. V.; Chernov, Yu. G., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 5.2, p. 960 - 969
  作者：Akhrem, A. A.、Borisov, E. V.、Chernov, Yu. G.

  DOI：——

  日期：——
• New Route of Reaction between Acyl Isothiocyanates and Cyclic  -Diketones
  作者：M. V. Vovk、N. G. Chubaruk、A. V. Bol'but

  DOI：10.1023/b:rujo.0000034955.48174.8f

  日期：2004.2
• AKHREM A. A.; LAKHVICH F. A.; BUDAI S. I.; KHLEBNICOVA T. S.; PETRUSEVICH+, SYNTHESIS, 1978, NO 12, 925-927
  作者：AKHREM A. A.、 LAKHVICH F. A.、 BUDAI S. I.、 KHLEBNICOVA T. S.、 PETRUSEVICH+

  DOI：——

  日期：——
• 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.