cryphonectric acid | 959981-91-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cryphonectric acid
• 英文别名: 4-(4,6-dihydroxy-3-oxo-1H-2-benzofuran-1-yl)-3,5-dihydroxybenzoic acid
• CAS: 959981-91-0
• 化学式: C₁₅H₁₀O₈
• 分子量: 318.24
• InChiKey: MYNCQCHJQQBWNF-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：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  145
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  cryphonectric acid 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.17h， 生成 3,5-Diacetoxy-4-(4,6-diacetoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)-benzoic acid methyl ester
  参考文献：
  名称：

  Cryphonectric Acid and Other Minor Metabolites from a Hypovirulent Strain of Cryphonectria parasitica

  摘要：

  Investigations carried out on secondary metabolites produced in culture by a hypovirulent strain of Cryphonectria parasitica allowed the isolation of several compounds which were characterized by NMR analysis and derivatization reactions. The most abundant metabolite was a new compound, called cryphonectric acid (1). Other metabolites were diaporthin, the only known phytotoxic compound isolated from both virulent and hypovirulent strains of C. parasitica, (+)-orthosporin, and L-p-hydroxyphenyllactic acid (HOPLA). Root growth activity of the purified compounds was evaluated both on tomato seedlings and maize subapical segments.

  DOI：

  10.1021/np0103012
• 作为产物：
  描述：

  methyl 4-(1,3-dihydro-4,6-dihydroxy-3-oxo-1-isobenzofuranyl)-3,5-dihydroxybenzoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以79%的产率得到cryphonectric acid
  参考文献：
  名称：

  区域特异性合成3-（2,6-二羟基苯基）邻苯二甲酸酯：在异黄霉素和冷冻柠檬酸合成中的应用

  摘要：

  已经开发出DBU催化的邻苯二甲酸和1，3-二酮的缩合反应，是合成3-取代的邻苯二甲酸酯的通用方法。该方法与乙酸汞介导的氧化芳构化相结合，已被用于异雌霉素（9）和冷柠檬酸（10）的区域特异性合成。

  DOI：

  10.1016/j.tet.2007.08.048

文献信息

• Regiospecific synthesis of 3-(2,6-dihydroxyphenyl)phthalides: application to the synthesis of isopestacin and cryphonectric acid
  作者：Dipakranjan Mal、Pallab Pahari、Saroj Ranjan De

  DOI：10.1016/j.tet.2007.08.048

  日期：2007.11

  DBU catalyzed condensation of phthalaldehydic acids and 1,3-diketones has been developed to be a general method for the synthesis of 3-substituted phthalides. This method, in combination with mercuric acetate mediated oxidative aromatization has been utilized for the regiospecific synthesis of isopestacin (9) and cryphonectric acid (10).

  已经开发出DBU催化的邻苯二甲酸和1，3-二酮的缩合反应，是合成3-取代的邻苯二甲酸酯的通用方法。该方法与乙酸汞介导的氧化芳构化相结合，已被用于异雌霉素（9）和冷柠檬酸（10）的区域特异性合成。
• Cryphonectric Acid and Other Minor Metabolites from a Hypovirulent Strain of <i>Cryphonectria </i><i>p</i><i>arasitica</i>
  作者：Alberto Arnone、Gemma Assante、Gianluca Nasini、Sara Strada、Annamaria Vercesi

  DOI：10.1021/np0103012

  日期：2002.1.1

  Investigations carried out on secondary metabolites produced in culture by a hypovirulent strain of Cryphonectria parasitica allowed the isolation of several compounds which were characterized by NMR analysis and derivatization reactions. The most abundant metabolite was a new compound, called cryphonectric acid (1). Other metabolites were diaporthin, the only known phytotoxic compound isolated from both virulent and hypovirulent strains of C. parasitica, (+)-orthosporin, and L-p-hydroxyphenyllactic acid (HOPLA). Root growth activity of the purified compounds was evaluated both on tomato seedlings and maize subapical segments.