methyl 3-(4,6-dimethoxy-3-oxoisobenzofuran-1(3H)-ylidene)propanoate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: methyl 3-(4,6-dimethoxy-3-oxoisobenzofuran-1(3H)-ylidene)propanoate
• 化学式: C₁₄H₁₄O₆
• 分子量: 278.262
• InChiKey: JWLQUOGEOJDPPO-WMZJFQQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  5,7-dimethoxyphthalide 、 methyl 3-methoxyprop-2-enoate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以18%的产率得到methyl 1,4-dihydroxy-6,8-dimethoxynaphthalene-2-carboxylate
  参考文献：
  名称：

  立体选择性合成顺式和反式-3,4-二氢-3,4,8-三羟基萘-1（2 H）-one

  摘要：

  Abstractmagnified imageA short and efficient protocol for the stereoselective synthesis of racemic trans‐ and cis‐3,4‐dihydro‐3,4,8‐trihydroxynaphthalen‐1(2H)‐one (1 and 2, resp.), is described, comprising nine and eight steps starting from commercial juglone (=5‐hydroxynaphthalene‐1,4‐dione; 12) (Scheme 4). Furthermore, an attempt to obtain 1 and 2 via phthalide annulation as the key step (Schemes 2 and 3) and a regioselective oxidation of the intermediate 1,2,3,4‐tetrahydronaphthalene‐1,2,4,5‐tetrols 27 and 28 with activated MnO2 were carried out (Scheme 4).

  DOI：

  10.1002/hlca.200800380

文献信息

• Stereoselective Synthesis of<i>cis-</i>and<i>trans</i>-3,4-Dihydro-3,4,8-trihydroxynaphthalen-1(2<i>H</i>)-one
  作者：Emmanuel Couché、Abdellatif Fkyerat、Raffaele Tabacchi

  DOI：10.1002/hlca.200800380

  日期：2009.5

  Abstractmagnified imageA short and efficient protocol for the stereoselective synthesis of racemic trans‐ and cis‐3,4‐dihydro‐3,4,8‐trihydroxynaphthalen‐1(2H)‐one (1 and 2, resp.), is described, comprising nine and eight steps starting from commercial juglone (=5‐hydroxynaphthalene‐1,4‐dione; 12) (Scheme 4). Furthermore, an attempt to obtain 1 and 2 via phthalide annulation as the key step (Schemes 2 and 3) and a regioselective oxidation of the intermediate 1,2,3,4‐tetrahydronaphthalene‐1,2,4,5‐tetrols 27 and 28 with activated MnO2 were carried out (Scheme 4).