2-oxo-6-benzoyl-2,3-dihydro-4H-1-benzopyran | 114031-68-4

• 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: 2-oxo-6-benzoyl-2,3-dihydro-4H-1-benzopyran
• 英文别名: 6-benzoyl-3,4-dihydro-2H-1-benzopyran-2-one；6-benzoyl-chroman-2-one；6-Benzoyl-chroman-2-on；6-benzoyl-3,4-dihydrochromen-2-one
• CAS: 114031-68-4
• 化学式: C₁₆H₁₂O₃
• 分子量: 252.269
• InChiKey: OGUBWEHEAMHDKW-UHFFFAOYSA-N

物化性质

• 熔点：
  128 °C
• 沸点：
  439.1±34.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  2-oxo-6-benzoyl-2,3-dihydro-4H-1-benzopyran 、 lithium diisopropyl amide 、 碘甲烷 以69%的产率得到
  参考文献：
  名称：

  MIYANO, MASATERU;DEASON, JAMES R.;NAKAO, AKIRA;STEALEY, MICHAEL A.;VILLAM+, J. MED. CHEM., 31,(1988) N 5, 1052-1061

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羟基-二苯甲酮 在 吡啶 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 jones' reagent 、 双氧水 、 potassium carbonate 、 N,N-二乙基苯胺 、 sodium iodide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 111.6h， 生成 2-oxo-6-benzoyl-2,3-dihydro-4H-1-benzopyran
  参考文献：
  名称：

  (Acyloxy)benzophenones and (acyloxy)-4-pyrones. A new class of inhibitors of human neutrophil elastase

  摘要：

  A series of 4-(acyloxy)- and 4,4'-bis(acyloxy)benzophenones were synthesized. Some of them, pivalates (trimethylacetates) and isobutyrates in particular, were found to be potent and selective inhibitors of human neutrophil (leukocyte) elastase. A series of 2-[(acyloxy)methyl]-5-(acyloxy)-4-pyrones were synthesized regioselectively from kojic acid. The 4-pyrones bearing a long chain acyl group at the 2-position and either pivaloyloxy or isobutyryloxy at the 5-position were potent and selective inhibitors of the human elastase. A number of analogues and derivatives in both series were synthesized in order to study the structure-activity relationship as summarized in Tables I-VI and in Tables IX and X. The inhibition was selective to human neutrophil elastase. No inhibition of porcine pancreatic elastase or bovine pancreatic chymotrypsin (Tables VII and XI) was observed. The most likely mechanism of inhibition is discussed. The implication of these findings for the treatment of rheumatoid arthritis and emphysema is outlined.

  DOI：

  10.1021/jm00400a030

文献信息

• Synthesis of 6-substituted-3,4-dihydro-2H-1-benzopyran-2-ones(dihydrocoumarins) via palladium catalysed coupling reactions
  作者：Stephen G. Davies、Dirk Pyatt、Colin Thomson

  DOI：10.1016/0022-328x(90)87186-h

  日期：1990.5
• Borsche; Hahn-Weinheimer, Chemische Berichte, 1952, vol. 85, p. 198,201
  作者：Borsche、Hahn-Weinheimer

  DOI：——

  日期：——
• DAVIES, STEPHEN G.;PYATT, DIRK;THOMSON, COLIN, J. ORGANOMET. CHEM., 387,(1990) N, C. 381-390
  作者：DAVIES, STEPHEN G.、PYATT, DIRK、THOMSON, COLIN

  DOI：——

  日期：——
• MIYANO, MASATERU;DEASON, JAMES R.;NAKAO, AKIRA;STEALEY, MICHAEL A.;VILLAM+, J. MED. CHEM., 31,(1988) N 5, 1052-1061
  作者：MIYANO, MASATERU、DEASON, JAMES R.、NAKAO, AKIRA、STEALEY, MICHAEL A.、VILLAM+

  DOI：——

  日期：——
• (Acyloxy)benzophenones and (acyloxy)-4-pyrones. A new class of inhibitors of human neutrophil elastase
  作者：Masateru Miyano、James R. Deason、Akira Nakao、Michael A. Stealey、Clara I. Villamil、Daniel D. Sohn、Richard A. Mueller

  DOI：10.1021/jm00400a030

  日期：1988.5

  A series of 4-(acyloxy)- and 4,4'-bis(acyloxy)benzophenones were synthesized. Some of them, pivalates (trimethylacetates) and isobutyrates in particular, were found to be potent and selective inhibitors of human neutrophil (leukocyte) elastase. A series of 2-[(acyloxy)methyl]-5-(acyloxy)-4-pyrones were synthesized regioselectively from kojic acid. The 4-pyrones bearing a long chain acyl group at the 2-position and either pivaloyloxy or isobutyryloxy at the 5-position were potent and selective inhibitors of the human elastase. A number of analogues and derivatives in both series were synthesized in order to study the structure-activity relationship as summarized in Tables I-VI and in Tables IX and X. The inhibition was selective to human neutrophil elastase. No inhibition of porcine pancreatic elastase or bovine pancreatic chymotrypsin (Tables VII and XI) was observed. The most likely mechanism of inhibition is discussed. The implication of these findings for the treatment of rheumatoid arthritis and emphysema is outlined.