5-methoxydihydroseselin

• 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: 5-methoxydihydroseselin
• 英文别名: 5-Methoxy-8,8-dimethyl-9,10-dihydropyrano[2,3-h]chromen-2-one
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: FFEMDYNYWWCISJ-UHFFFAOYSA-N

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：

  5-methoxydihydroseselin 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 4.0h， 以57%的产率得到5-甲氧基邪蒿素
  参考文献：
  名称：

  水中的5-甲氧芝麻素和四氧嘧啶无氧骨架的无催化剂一锅结构

  摘要：

  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。

  DOI：

  10.1021/ol401581p
• 作为产物：
  描述：

  3,3-二甲基丙烯酸 在 盐酸 、 甲酸 、 tris(dibenzylideneacetone)dipalladium (0) 、 zinc(II) chloride 、 锌 、 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 5-methoxydihydroseselin
  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

• Prenylated Coumarins: Natural Phosphodiesterase-4 Inhibitors from <i>Toddalia asiatica</i>
  作者：Ting-Ting Lin、Yi-You Huang、Gui-Hua Tang、Zhong-Bin Cheng、Xin Liu、Hai-Bin Luo、Sheng Yin

  DOI：10.1021/np401040d

  日期：2014.4.25

  Bioassay-guided fractionation of the ethanolic extract of the roots of Toddalia asiatica led to the isolation of seven new prenylated coumarins (1–7) and 14 known analogues (8–21). The structures of 1–7 were elucidated by spectroscopic analysis, and their absolute configurations were determined by combined chemical methods and chiral separation analysis. Compounds 1–5, named toddalin A, 3‴-O-demethyltoddalin

  生物测定法指导的Toddalia asiatica根部乙醇提取物的分馏导致分离出七种新的烯丙基香豆素（1 – 7）和14种已知的类似物（8 – 21）。通过光谱分析阐明了1 – 7的结构，并通过化学方法和手性分离分析确定了它们的绝对构型。化合物1 - 5，命名toddalin A，3''' - ø -demethyltoddalin A，和toddalins B-d，代表苯基丙烯酸偶联异戊二烯化香豆素的一个不寻常的基团。化合物1 – 21并使用tri标记的腺苷3'，5'-环一磷酸（[ 3 H] -cAMP）作为底物，针对其对磷酸二酯酶4（PDE4）的抑制活性，筛选了四个修饰的类似物10a，11a，13a和17a。），这是治疗哮喘和慢性阻塞性肺疾病的药物靶标。化合物3，8，10，10A，11，11A，12，13，17，和21展出抑制作用IC 50值小于10μM。活性最高的化合物Toddacoumalone（8）（IC
• Acridone alkaloids and a coumarin from Citrus grandis
  作者：Wu Tian-Shung、Kuoh Chang-Sheng、Hiroshi Furukawa

  DOI：10.1016/s0031-9422(00)84044-3

  日期：1983.1

  Abstract The constituents of the root bark of Citrus grandis f. hakunikuyu were studied and new acridone alkaloids, grandisinine, grandisine-I, and grandisine-II, and a new coumarin, 5-methoxyseselin, were isolated and characterized.

  摘要 Citrus grandis f. 根皮的成分。对 hakunikuyu 进行了研究，并分离并表征了新的吖啶酮生物碱、grandisinine、grandisine-I 和grandisine-II，以及一种新的香豆素、5-甲氧基芝麻素。
• Atom Economy. Palladium-Catalyzed Formation of Coumarins by Addition of Phenols and Alkynoates via a Net C−H Insertion
  作者：Barry M. Trost、F. Dean Toste、Kevin Greenman

  DOI：10.1021/ja0286573

  日期：2003.4.1

  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.
• 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。