5-Hydroxy-8,8-dimethyl-7,8-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester | 88296-07-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-Hydroxy-8,8-dimethyl-7,8-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester
• CAS: 88296-07-5
• 化学式: C₁₆H₁₈O₅
• 分子量: 290.316
• InChiKey: FBUCIUZLGTVBJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-Hydroxy-8,8-dimethyl-7,8-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester 在 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以93%的产率得到4,4-dimethyl-2-(ethoxycarbonyl)-6,7-(methylenedioxy)-1(2H)-naphthalenone
  参考文献：
  名称：

  Structure-activity relationships among DNA gyrase inhibitors. Synthesis and biological evaluation of 1,2-dihydro-4,4-dimethyl-1-oxo-2-naphthalenecarboxylic acids as 1-carba bioisosteres of oxolinic acid

  摘要：

  A series of oxolinic acid analogues was synthesized in an attempt to evaluate the role, if any, played by the N-1 atom in putative modes of action of antimicrobial DNA gyrase inhibitors. Carba analogues were prepared because these have no possibility of an internal resonance contribution of the nitrogen atom and yet could otherwise satisfy electronic requirements of putative modes of action. Successful routes were developed involving Friedel-Craft's cycloaddition of suitable aromatic compounds with 4,4-dimethylbutyrolactone, followed by ethoxycarbonylation, oxidation with dichlorodicyanobenzoquinone, and careful saponification. The gem-dimethyl group of these analogues prevents aromatization at the cost of nonplanarity. Only the unsubstituted parent compound, 1,2-dihydro-4,4-dimethyl-1-oxo-2-naphthalenecarboxylic acid, possessed any appreciable antimicrobial activity in vitro. This may be due to a different mode of action, however, since gave no measurable inhibition of DNA gyrase in vitro. Thus, the N-1 atom plays a significant role in enzymic and bacteriological inhibition that cannot be compensated for by the presence of C-6 oxygen atoms.

  DOI：

  10.1021/jm00369a013
• 作为产物：
  描述：

  6,7-二甲氧基-4,4-二甲基-2,3-二氢萘-1-酮 在 三溴化硼 、 sodium hydride 、 potassium carbonate 、 copper(II) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 5-Hydroxy-8,8-dimethyl-7,8-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester
  参考文献：
  名称：

  Structure-activity relationships among DNA gyrase inhibitors. Synthesis and biological evaluation of 1,2-dihydro-4,4-dimethyl-1-oxo-2-naphthalenecarboxylic acids as 1-carba bioisosteres of oxolinic acid

  摘要：

  A series of oxolinic acid analogues was synthesized in an attempt to evaluate the role, if any, played by the N-1 atom in putative modes of action of antimicrobial DNA gyrase inhibitors. Carba analogues were prepared because these have no possibility of an internal resonance contribution of the nitrogen atom and yet could otherwise satisfy electronic requirements of putative modes of action. Successful routes were developed involving Friedel-Craft's cycloaddition of suitable aromatic compounds with 4,4-dimethylbutyrolactone, followed by ethoxycarbonylation, oxidation with dichlorodicyanobenzoquinone, and careful saponification. The gem-dimethyl group of these analogues prevents aromatization at the cost of nonplanarity. Only the unsubstituted parent compound, 1,2-dihydro-4,4-dimethyl-1-oxo-2-naphthalenecarboxylic acid, possessed any appreciable antimicrobial activity in vitro. This may be due to a different mode of action, however, since gave no measurable inhibition of DNA gyrase in vitro. Thus, the N-1 atom plays a significant role in enzymic and bacteriological inhibition that cannot be compensated for by the presence of C-6 oxygen atoms.

  DOI：

  10.1021/jm00369a013