3-Deoxyzinnolide; 6-[(3',3'-二甲基烯丙基)氧基]-4-甲氧基-5-甲基苯酞 | 17811-32-4

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 中文名称: 3-Deoxyzinnolide; 6-[(3',3'-二甲基烯丙基)氧基]-4-甲氧基-5-甲基苯酞
• 中文别名: 3-Deoxyzinnolide;6-[(3',3'-二甲基烯丙基)氧基]-4-甲氧基-5-甲基苯酞
• 英文名称: 6-(3',3'-dimethylallyloxy)-4-methoxy-5-methylphthalide
• 英文别名: 4-methoxy-5-methyl-6-(3-methyl-2-butenyloxy)-phthalide；1(3H)-Isobenzofuranone, 4-methoxy-5-methyl-6-((3-methyl-2-butenyl)oxy)-；4-methoxy-5-methyl-6-(3-methylbut-2-enoxy)-3H-2-benzofuran-1-one
• CAS: 17811-32-4
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: BGCNHXQQGSIHRP-UHFFFAOYSA-N

物化性质

• 沸点：
  448.6±45.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 储存条件：
  存储条件：2-8℃，干燥，密闭。

反应信息

• 作为反应物：
  描述：

  3-Deoxyzinnolide; 6-[(3',3'-二甲基烯丙基)氧基]-4-甲氧基-5-甲基苯酞 在 甲醇 、 potassium carbonate 作用下， 反应 7.0h， 生成 2-hydroxymethyl-3-methoxy-4-methyl-5-(3-methyl-but-2-enyloxy)-benzoic acid
  参考文献：
  名称：

  Natural Zinniol Derivatives from Alternaria tagetica. Isolation, Synthesis, and Structure−Activity Correlation

  摘要：

  Two novel phytotoxins, 8-zinniol methyl ether (5) and 8-zinniol acetate (6), in addition to 6-(3',3'dimethylallyloxy)-4-methoxy-5-methylphthalide (2), 5-(3',3'-dimethylallyloxy)-7-methoxy-6-methylphthalide (3), and the novel metabolites 8-zinniol 2-(phenyl)ethyl ether (4) and 7-zinniol acetate (7) have been identified as natural zinniol derivatives from the organic crude extract of Alternaria tagetica culture filtrates. Using zinniol as the starting material, phytotoxin 5 was synthesized, together with a number of synthetic intermediates (8-13). Both natural and synthetic zinniol derivatives were evaluated in the leaf-spot bioassay against marigold leaves (Tagetes erecta).

  DOI：

  10.1021/jf010641t
• 作为产物：
  描述：

  methyl 2-formyl-3,5-dihydroxy-4-methylbenzoate 在 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 20.25h， 生成 3-Deoxyzinnolide; 6-[(3',3'-二甲基烯丙基)氧基]-4-甲氧基-5-甲基苯酞
  参考文献：
  名称：

  The synthesis of zinniol

  摘要：

  DOI：

  10.1016/s0040-4020(01)93696-8

文献信息

• Incorporation of carbon dioxide into phthalides via ligand-free copper-catalyzed direct carboxylation of benzoxasiloles
  作者：Thanh V. Q. Nguyen、José A. Rodríguez-Santamaría、Woo-Jin Yoo、Shū Kobayashi

  DOI：10.1039/c7gc00917h

  日期：——

  The direct carboxylation of benzoxasiloles with carbon dioxide proceeded smoothly under mild conditions using copper iodide as a catalyst to afford phthalides after an acid work-up. Broad substrate scope and application of this methodology for the synthesis of natural products highlight the synthetic utility of this protocol.

  在弱酸条件下，使用碘化铜作为催化剂，在温和的条件下，苯并二甲酚与二氧化碳的直接羧化反应顺利进行，从而在酸处理后得到邻苯二甲酸盐。该方法在天然产物合成中的广泛底物范围和应用突出了该方案的合成效用。
• Hariprakasha; Subba Rao, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 9, p. 851 - 856
  作者：Hariprakasha、Subba Rao

  DOI：——

  日期：——
• The structure of zinnolide, a new phytotoxin from Alternaria solani.
  作者：Akitami ICHIHARA、Hiroyuki TAZAKI、Sadao SAKAMURA

  DOI：10.1271/bbb1961.49.2811

  日期：——
• The synthesis of zinniol
  作者：J.A. Martin、E. Vogel

  DOI：10.1016/s0040-4020(01)93696-8

  日期：1980.1
• Natural Zinniol Derivatives from <i>Alternaria tagetica</i>. Isolation, Synthesis, and Structure−Activity Correlation
  作者：M. Marcela Gamboa-Angulo、Fabiola Escalante-Erosa、Karlina García-Sosa、Fátima Alejos-González、Guillermo Delgado-Lamas、Luis M. Peña-Rodríguez

  DOI：10.1021/jf010641t

  日期：2002.2.1

  Two novel phytotoxins, 8-zinniol methyl ether (5) and 8-zinniol acetate (6), in addition to 6-(3',3'dimethylallyloxy)-4-methoxy-5-methylphthalide (2), 5-(3',3'-dimethylallyloxy)-7-methoxy-6-methylphthalide (3), and the novel metabolites 8-zinniol 2-(phenyl)ethyl ether (4) and 7-zinniol acetate (7) have been identified as natural zinniol derivatives from the organic crude extract of Alternaria tagetica culture filtrates. Using zinniol as the starting material, phytotoxin 5 was synthesized, together with a number of synthetic intermediates (8-13). Both natural and synthetic zinniol derivatives were evaluated in the leaf-spot bioassay against marigold leaves (Tagetes erecta).