2,2-Dimethyl-propionic acid 6-(2,2-dimethyl-propionyloxymethyl)-4-oxo-4H-pyran-3-yl ester | 114031-86-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2,2-Dimethyl-propionic acid 6-(2,2-dimethyl-propionyloxymethyl)-4-oxo-4H-pyran-3-yl ester
• 英文别名: [5-(2,2-dimethylpropanoyloxy)-4-oxopyran-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 114031-86-6
• 化学式: C₁₆H₂₂O₆
• 分子量: 310.347
• InChiKey: GFQJNMAZHWYPCH-UHFFFAOYSA-N

物化性质

• 熔点：
  95-97 °C
• 沸点：
  423.9±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  碘代叔丁烷 、 2,2-Dimethyl-propionic acid 6-(2,2-dimethyl-propionyloxymethyl)-4-oxo-4H-pyran-3-yl ester 在 chiral Al-salen derivative 三乙基硼 、 氧气 、 三正丁基氢锡 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成 、 2,2-Dimethyl-propionic acid (2S,3R)-2-tert-butyl-6-(2,2-dimethyl-propionyloxymethyl)-4-oxo-3,4-dihydro-2H-pyran-3-yl ester
  参考文献：
  名称：

  Pyrones to Pyrans:  Enantioselective Radical Additions to Acyloxy Pyrones

  摘要：

  This paper describes a highly site-, diastereo-, and enantioselective intermolecular radical addition/hydrogen atom transfer to hydroxypyrone pyromeconic and kojic acids. The methodology can be extended to the formation of chiral quaternary centers. The products obtained are densely functionalized pyran moieties. The products contain structural features amenable for the introduction of additional substituents.

  DOI：

  10.1021/ja0648108
• 作为产物：
  描述：

  曲酸 在 吡啶 、 盐酸 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 2,2-Dimethyl-propionic acid 6-(2,2-dimethyl-propionyloxymethyl)-4-oxo-4H-pyran-3-yl ester
  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

• 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.
• Pyrones to Pyrans:  Enantioselective Radical Additions to Acyloxy Pyrones
  作者：Mukund P. Sibi、Jake Zimmerman

  DOI：10.1021/ja0648108

  日期：2006.10.1

  This paper describes a highly site-, diastereo-, and enantioselective intermolecular radical addition/hydrogen atom transfer to hydroxypyrone pyromeconic and kojic acids. The methodology can be extended to the formation of chiral quaternary centers. The products obtained are densely functionalized pyran moieties. The products contain structural features amenable for the introduction of additional substituents.