(E)-2-(4-hydroxy-4-(thiophen-2-yl)but-1-enyl)-6-methoxy-3,5-dimethyl-4H-pyran-4-one | 1343490-40-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (E)-2-(4-hydroxy-4-(thiophen-2-yl)but-1-enyl)-6-methoxy-3,5-dimethyl-4H-pyran-4-one
• 英文别名: 2-[(E)-4-hydroxy-4-thiophen-2-ylbut-1-enyl]-6-methoxy-3,5-dimethylpyran-4-one
• CAS: 1343490-40-3
• 化学式: C₁₆H₁₈O₄S
• 分子量: 306.383
• InChiKey: NZGVAUOMXINXJV-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  84
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-噻吩甲醛 、 α,α′-dimethoxy-γ-pyrone 、 烯丙基三丁基锡 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以43%的产率得到(E)-2-(4-hydroxy-4-(thiophen-2-yl)but-1-enyl)-6-methoxy-3,5-dimethyl-4H-pyran-4-one
  参考文献：
  名称：

  One-Pot Regio- and Stereoselective Synthesis of α′-Methoxy-γ-pyrones: Biological Evaluation as Mitochondrial Respiratory Complex Inhibitors

  摘要：

  The one-pot construction of functionalized alpha'-methoxy-gamma-pyrones is detailed. Starting from alpha,alpha'-dimethoxy-gamma-pyrone, molecular diversity is attained by a regio- and stereoselective desymmetrization using allyllithium followed by vinylogous aldol reaction. Mechanistic considerations including density functional theory calculations and insightful experiments have been gathered to shed light on this complex multistep process. To illustrate the versatility of this methodology, some of the molecules prepared were evaluated for their ability to inhibit NADH-oxidase and NADH-ubiquinone oxidoreductase. In the process, a potent new inihibitor of NADH-oxidase activity (IC50 44 nM) was identified.

  DOI：

  10.1021/jo201683u

文献信息

• One-Pot Regio- and Stereoselective Synthesis of α′-Methoxy-γ-pyrones: Biological Evaluation as Mitochondrial Respiratory Complex Inhibitors
  作者：Helena Rosso、Michaël De Paolis、Valérie C. Collin、Sriloy Dey、Sidney M. Hecht、Cristina Prandi、Vincent Richard、Jacques Maddaluno

  DOI：10.1021/jo201683u

  日期：2011.11.18

  The one-pot construction of functionalized alpha'-methoxy-gamma-pyrones is detailed. Starting from alpha,alpha'-dimethoxy-gamma-pyrone, molecular diversity is attained by a regio- and stereoselective desymmetrization using allyllithium followed by vinylogous aldol reaction. Mechanistic considerations including density functional theory calculations and insightful experiments have been gathered to shed light on this complex multistep process. To illustrate the versatility of this methodology, some of the molecules prepared were evaluated for their ability to inhibit NADH-oxidase and NADH-ubiquinone oxidoreductase. In the process, a potent new inihibitor of NADH-oxidase activity (IC50 44 nM) was identified.