methyl 5-hydroxy-7-methyl-4-oxo-2-(5-oxooxolan-2-yl)-3H-chromene-2-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: methyl 5-hydroxy-7-methyl-4-oxo-2-(5-oxooxolan-2-yl)-3H-chromene-2-carboxylate
• 化学式: C₁₆H₁₆O₇
• 分子量: 320.299
• InChiKey: LKWYUESLGBROHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  99.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 5-hydroxy-7-methyl-4-oxo-2-(5-oxooxolan-2-yl)-3H-chromene-2-carboxylate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以37%的产率得到blennolide C
  参考文献：
  名称：

  Vinylogous Addition of Siloxyfurans to Benzopyryliums: A Concise Approach to the Tetrahydroxanthone Natural Products

  摘要：

  A concise approach to the tetrahydroxanthone natural products employing vinylogous addition of siloxyfurans to benzopyryliums and a late-stage Dieckmann cyclization has been developed. With this methodology, chiral, racemic forms of the natural products blennolides B and blennolide C have been synthesized in a maximum of four steps from a 5-hydroxychromone substrate. The regio- and diastereoselectivity of the vinylogous additions was probed using computational studies, which suggested the involvement of Diets Alder-like transition states.

  DOI：

  10.1021/ja110698n

文献信息

• Vinylogous Addition of Siloxyfurans to Benzopyryliums: A Concise Approach to the Tetrahydroxanthone Natural Products
  作者：Tian Qin、Richard P. Johnson、John A. Porco

  DOI：10.1021/ja110698n

  日期：2011.2.16

  A concise approach to the tetrahydroxanthone natural products employing vinylogous addition of siloxyfurans to benzopyryliums and a late-stage Dieckmann cyclization has been developed. With this methodology, chiral, racemic forms of the natural products blennolides B and blennolide C have been synthesized in a maximum of four steps from a 5-hydroxychromone substrate. The regio- and diastereoselectivity of the vinylogous additions was probed using computational studies, which suggested the involvement of Diets Alder-like transition states.