5-hydroxy-2-(1-hydroxy-1-methyl-ethyl)-naphtho[1,2-b]furan-4-carboxylic acid methyl ester | 849591-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 5-hydroxy-2-(1-hydroxy-1-methyl-ethyl)-naphtho[1,2-b]furan-4-carboxylic acid methyl ester
• 英文别名: Methyl 5-hydroxy-2-(2-hydroxypropan-2-yl)benzo[g][1]benzofuran-4-carboxylate
• CAS: 849591-14-6
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: VGNXSXIRYQFQJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  79.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-hydroxy-2-(1-hydroxy-1-methyl-ethyl)-naphtho[1,2-b]furan-4-carboxylic acid methyl ester 、 3-((E)-3-hydroxy-3-methyl-but-1-enyl)-1,4-dioxo-1,4-dihydro-naphthalene-2-carboxylic acid methyl ester 在 苯硼酸 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以67%的产率得到5-hydroxy-2-isopropenyl-naphtho[1,2-b]furan-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Biomimetic Synthesis and Structure Elucidation of Rubicordifolin, a Cytotoxic Natural Product from Rubia cordifolia

  摘要：

  The biomimetic synthesis and full structural elucidation of rubicordifolin, a cytotoxic natural product isolated from Rubia cordifolia, is described.

  DOI：

  10.1021/ja042375g
• 作为产物：
  描述：

  2-methoxycarbonyl-1,4-naphthoquinone 在 正丁基锂 、 ammonium cerium(IV) nitrate 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 121.01h， 生成 5-hydroxy-2-(1-hydroxy-1-methyl-ethyl)-naphtho[1,2-b]furan-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Biomimetic Synthesis and Structure Elucidation of Rubicordifolin, a Cytotoxic Natural Product from Rubia cordifolia

  摘要：

  The biomimetic synthesis and full structural elucidation of rubicordifolin, a cytotoxic natural product isolated from Rubia cordifolia, is described.

  DOI：

  10.1021/ja042375g

文献信息

• Theoretical Investigation of the Rubicordifolin Cascade
  作者：Jean-Philip Lumb、Jamin L. Krinsky、Dirk Trauner

  DOI：10.1021/ol102157d

  日期：2010.11.19

  The results of a theoretical investigation on the complex cascade reaction leading to the natural product rubicordifolin are reported. These computations analyze the discrete transformations that are required during the conversion of the vinyl naphthoquinone starting material into the natural product, including two pseudopericyclic cyclizations as well as a diastereoselective, hetero-Diels-Alder reaction.