dihydroxanthoxyletin | 17053-75-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: dihydroxanthoxyletin
• 英文别名: Kanzonol Q；5-methoxy-2,2-dimethyl-3,4-dihydropyrano[3,2-g]chromen-8-one
• CAS: 17053-75-7
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: HJUDWPJIBKIYQS-UHFFFAOYSA-N

物化性质

• 熔点：
  140-144 °C
• 沸点：
  432.5±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• 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

反应信息

• 作为反应物：
  描述：

  dihydroxanthoxyletin 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 20.0h， 以75%的产率得到黄木亭
  参考文献：
  名称：

  Atom Economy. Palladium-Catalyzed Formation of Coumarins by Addition of Phenols and Alkynoates via a Net C−H Insertion

  摘要：

  A strategy to achieve ortho substitution of phenols initiated by an ortho-palladation to create coumarins was examined. Indeed, treatment of alkynoates with electron-rich phenols in the presence of a palladium catalyst and an acid does generate coumarins. The scope of the reaction with respect to the phenol and the alkynoates is defined. With unsymmetrical aromatic substrates, generally good regioselectivity that reflects the HOMO coefficients can be observed. In the course of these studies, numerous important naturally occurring coumarins have been synthesized, including fraxinol methyl ether, ayapin, herniarin, xanthoxyletin, and alloxanthoxyletin. The fact that a Pd(0) is the precatalyst rather than a Pd(+2) species and that an acid that reduces Pd(+2) salts, formic acid, functions better than other carboxylic acids raises doubts about the initial working hypothesis. A novel mechanism involving a palladium phenoxide formed from a hydridopalladium carboxylate and phenol is invoked to rationalize the results.

  DOI：

  10.1021/ja0286573
• 作为产物：
  描述：

  3,3-二甲基丙烯酸 在 盐酸 、 palladium diacetate 、 氢氧化钾 、 甲酸 、 sodium acetate 、 potassium carbonate 、 zinc(II) chloride 、 锌 、 三氯氧磷 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 52.0h， 生成 dihydroxanthoxyletin
  参考文献：
  名称：

  Atom Economy. Palladium-Catalyzed Formation of Coumarins by Addition of Phenols and Alkynoates via a Net C−H Insertion

  摘要：

  A strategy to achieve ortho substitution of phenols initiated by an ortho-palladation to create coumarins was examined. Indeed, treatment of alkynoates with electron-rich phenols in the presence of a palladium catalyst and an acid does generate coumarins. The scope of the reaction with respect to the phenol and the alkynoates is defined. With unsymmetrical aromatic substrates, generally good regioselectivity that reflects the HOMO coefficients can be observed. In the course of these studies, numerous important naturally occurring coumarins have been synthesized, including fraxinol methyl ether, ayapin, herniarin, xanthoxyletin, and alloxanthoxyletin. The fact that a Pd(0) is the precatalyst rather than a Pd(+2) species and that an acid that reduces Pd(+2) salts, formic acid, functions better than other carboxylic acids raises doubts about the initial working hypothesis. A novel mechanism involving a palladium phenoxide formed from a hydridopalladium carboxylate and phenol is invoked to rationalize the results.

  DOI：

  10.1021/ja0286573

文献信息

• A Catalyst-Free One-Pot Construction of Skeletons of 5-Methoxyseselin and Alloxanthoxyletin in Water
  作者：Jin-Li Cao、Su-Li Shen、Peng Yang、Jin Qu

  DOI：10.1021/ol401581p

  日期：2013.8.2

  In refluxing water and without an additional catalyst, electron-rich phenols could react with alkynoic acids or alkynoates to provide coumarin structures. The skeletons of two natural pyranocoumarins, 5-methoxyseselin and alloxanthoxyletin, could be constructed (total yield up to 76%) in an aqueous multicomponent reaction in which isoprenyl acetate, propiolic acid, and phloroglucinol were simply mixed

  在回流水中且没有其他催化剂的情况下，富含电子的酚可能与炔酸或炔酸反应生成香豆素结构。可以在水性多组分反应中构建两种天然吡喃香豆素的骨架，即5-甲氧基水杨素和别氧蒽氧基letletanthoxyletin（总收率高达76％），其中将异戊二烯乙酸酯，丙酸和间苯三酚简单地混合并在水中回流。
• 58. Constituents of Zanthoxylum americanum(Mill). Part III. The constitution of xanthoxyletin
  作者：Alexander Robertson、T. S. Subramaniam

  DOI：10.1039/jr9370000286

  日期：——
• Bell et al., Journal of the Chemical Society, 1936, p. 627,632
  作者：Bell et al.

  DOI：——

  日期：——
• Über einen Inhaltsstoff von Xanthoxylum fraxineum Wild
  作者：H. Dieterle、E. Kruta

  DOI：10.1002/ardp.19372750107

  日期：——
• Gordin, Journal of the American Chemical Society, 1906, vol. 28, p. 1650
  作者：Gordin

  DOI：——

  日期：——