9-hydroxy-8-methoxynaphtho[2,3-c]furan-1(3H)-one | 92379-25-4

• 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: 9-hydroxy-8-methoxynaphtho[2,3-c]furan-1(3H)-one
• 英文别名: 1-Hydroxy-3-hydroxymethyl-8-methoxy-naphthoesaeure-(2)-γ-lacton；9-hydroxy-8-methoxy-3H-naphtho[2,3-c]furan-1-one；9-Hydroxy-8-methoxy-3H-naphtho[2,3-c]furan-1-on；4-hydroxy-5-methoxy-1H-benzo[f][2]benzofuran-3-one
• CAS: 92379-25-4
• 化学式: C₁₃H₁₀O₄
• 分子量: 230.22
• InChiKey: UXBYTYHNTWKINC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  β-sorigenin 1-O-β-D-glucoside permethyl ether 在 盐酸 作用下， 以18 mg的产率得到9-hydroxy-8-methoxynaphtho[2,3-c]furan-1(3H)-one
  参考文献：
  名称：

  A naphthalene glucoside lactone from Rhamnus wightii

  摘要：

  A new naphthalene glucoside lactone was isolated from the acetone extract of the stem bark of Rhamnus wightii. Cynodontin, chrysophanol, physcion, musizin, lupeol, sitosterol, 7-hydroxy-5-methoxyphthalide, emodin, sitosterol glycoside, beta-sorigenin are the known compounds; beta-sorigenin may be an artifact of its glucoside. The co-occurrence of two lactone ring compounds, 7-hydroxy-5-methoxyphthalide and the naphthalide glucoside is the significant feature of this plant.

  DOI：

  10.1016/0031-9422(91)83502-c

文献信息

• Transpositive Tandem Annulation of Phthalides with Allene Carboxylates: Regioselective Synthesis of Arylnaphthalene Lignans
  作者：Dipakranjan Mal、Supriti Jana

  DOI：10.1021/acs.joc.6b02313

  日期：2016.12.2

  Allene carboxylates, scarcely used as Michael acceptors, serve as acceptors in the annulation with phthalides in the presence of LDA and provide a one-pot synthesis of naphtho[c]furanones in very good yields. This tandem annulation is proposed to proceed via transposition of the hydroxy group resulting from the initial annulation.

  几乎不用作迈克尔受体的丙二烯羧酸盐在LDA存在下与邻苯二甲酸酯成环时用作受体，并以非常高的收率提供一锅法合成萘并[ c ]呋喃酮。提出这种串联环化是通过由初始环化产生的羟基的转位进行的。
• Nikuni; Hitsumoto, Nippon Nogeikagaku Kaishi, 1944, vol. 20, p. 283,286
  作者：Nikuni、Hitsumoto

  DOI：——

  日期：——