N-(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)benzamide | 23674-57-9

• 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: N-(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)benzamide
• 英文别名: Benzamide, N-(5,5-dimethyl-3-oxo-1-cyclohexen-1-yl)-；N-(5,5-dimethyl-3-oxocyclohexen-1-yl)benzamide
• CAS: 23674-57-9
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: XAXJAVCKMWVKNB-UHFFFAOYSA-N

物化性质

• 熔点：
  144-146 °C
• 沸点：
  422.6±45.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 在 copper(l) iodide 、 N,N-二甲基甘氨酸 、 碘 、 caesium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 84.0h， 生成 N-(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)benzamide
  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

• Enaminones 9. Further studies on the anticonvulsant activity and potential type IV phosphodiesterase inhibitory activity of substituted vinylic benzamides
  作者：Alan J. Anderson、Jesse M. Nicholson、Oladapo Bakare、Ray J. Butcher、Tiffany L. Wilson、K.R. Scott

  DOI：10.1016/j.bmc.2005.09.023

  日期：2006.2

  Structure-activity relationship studies were employed to synthesize a series of 3- and 3,4-substituted benzamides from 3-amino-2-cyclohexenones. An improved method for the synthesis of benzamides from 3-amino-2-cyclohexenones is presented which provided significantly higher yields (71-79%) for the reported compounds. NMR and X-ray structural analyses were undertaken to note the possible intra- and intermolecular

  结构-活性关系研究用于从3-氨基-2-环己烯酮合成一系列3-和3,4-取代的苯甲酰胺。提出了一种从3-氨基-2-环己烯酮合成苯甲酰胺的改进方法，该方法为所报道的化合物提供了明显更高的收率（71-79％）。进行了NMR和X射线结构分析，以发现合成类似物可能的分子内和分子间相互作用。分子模型研究被用来确定最小化的构型，并与它们的X射线结构进行了相关性比较。这些新实体被评估为潜在的抗惊厥药和IV型磷酸二酯酶抑制剂（PDE4）。
• Synthesis, characterization and anticonvulsant activity of enaminones. Part 6: Synthesis of substituted vinylic benzamides as potential anticonvulsants
  作者：James E. Foster、Jesse M. Nicholson、Raymond Butcher、James P. Stables、Ivan O. Edafiogho、Angela M. Goodwin、Michael C. Henson、Carlynn A. Smith、K.R. Scott

  DOI：10.1016/s0968-0896(99)00185-6

  日期：1999.11

  A comparison of enaminones from various unsubstituted and p-substituted benzamides to the analogous benzylamines has been undertaken with the aim of elucidating the essential structural parameters necessary for anticonvulsant activity. Initial studies on methyl 4-N-(benzylamino)-6-methyl-2-oxocyclohex-3-en-1-oate, 3a, 3-N-(benzylamino)cyclohex-2-en-1-one, 3p, and 5,5-dimethyl-3-N-(benzylamino)-cyclohex-2-en-1-one

  为了阐明抗惊厥活性所必需的基本结构参数，已经进行了将各种未取代和对位取代的苯甲酰胺中的烯胺酮与类似的苄胺进行比较。对4-N-（苄氨基）-6-甲基-2-氧代环己-3-烯-1-酸酯，3a，3-N-（苄基氨基）环己-2-烯-1-酮，3p和5,5-二甲基-3-N-（苄氨基）-环己-2-烯-1-酮，3r表示苄胺具有明显的最大抗电击癫痫发作（MES）活性。对类似苯甲酰胺的评估表明，其抗惊厥活性存在显着差异，这些差异很可能与它们三维结构的差异有关。
• Vinylogous imides. II. Ultraviolet spectra and the application of Woodward's rules
  作者：Daryl L. Ostercamp

  DOI：10.1021/jo00830a080

  日期：1970.5
• 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.