methyl 3-oxo-3H-benzo[ f ]chromene-1-carboxylate | 474093-34-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: methyl 3-oxo-3H-benzo[ f ]chromene-1-carboxylate
• 英文别名: Methyl-3-oxo-3h-benzo[f]chromene-1-carboxylate；methyl 3-oxobenzo[f]chromene-1-carboxylate
• CAS: 474093-34-0
• 化学式: C₁₅H₁₀O₄
• 分子量: 254.242
• InChiKey: DECLYKCNBVHAOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 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：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丁炔二酸二甲酯 、 三苯基膦 、 methyl 3-oxo-3H-benzo[ f ]chromene-1-carboxylate 以 二氯甲烷 为溶剂， 生成 Butanedioic acid,(2-hydroxy-1-naphthalenyl)(triphenylphosphoranylidene)-, dimethyl ester
  参考文献：
  名称：

  Silica Gel Catalyzed Conversion of Dialkyl 2-(2-Hydroxy-1-naphthyl)-3-(1,1,1-triphenyl-λ 5 -phosphanylidene) Succinates to Alkyl 3-Oxo-3 H -benzo[ f ]chromene-1-carboxylates in Solvent-free Conditions

  摘要：

  Protonation of the highly reactive 1:1 intermediates produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates by 2-hydroxynaphthalene leads to vinyltriphenylphosphonium salts, which undergo aromatic electrophilic substitution reaction with conjugate base to produce dialkyl 2-(1-hydroxy-2-naphthyl)-3-(1,1,1-triphenyl-lambda(5)-phosphanylidene) succinates. Silica gel was found to catalyze conversion of dialkyl 2-(1-hydroxy-2-naphthyl)-3-(1,1,1-triphenyl-lambda(5)-phosphanylidene) succinates to alkyl 3-oxo-3H-benzo[f]chromene-1-carboxylates in solvent-free conditions at 60degreesC in fairly good yields.

  DOI：

  10.1080/10426500307901
• 作为产物：
  描述：

  Butanedioic acid,(2-hydroxy-1-naphthalenyl)(triphenylphosphoranylidene)-, dimethyl ester 在 silica gel 作用下， 反应 0.05h， 生成 methyl 3-oxo-3H-benzo[ f ]chromene-1-carboxylate
  参考文献：
  名称：

  在无溶剂条件下，在硅胶粉末存在的情况下，微波诱导合成香豆素，原位生成稳定的磷叶立德

  摘要：

  苯酚（1-羟基萘、2-羟基萘和4-溴苯酚）对三苯基膦和二烷基乙炔二羧酸酯反应产生的高反应性1:1中间体进行质子化，生成乙烯基三苯基鏻盐，与共轭碱发生芳香族亲电取代反应，得到产生相应的稳定磷叶立德。发现微波在无溶剂条件下在硅胶粉末存在下催化稳定的磷叶立德转化为相应的香豆素。

  DOI：

  10.1080/10426500490422173

文献信息

• Phosphinite ionic liquid (IL-OPPh2) as a recyclable reagent for the efficient synthesis of coumarins under microwave irradiation conditions
  作者：H. Valizadeh、H. Gholipour、M. Mahmoudian

  DOI：10.1007/bf03245917

  日期：2011.9

  the efficient synthesis of 4-substituted coumarins via the reaction of di(methyl or ethyl) acetylenedicarboxylate with phenolic compounds under microwave irradiation conditions. The effects of parameters such as the amount of the phosphinite ionic liquid, reaction temperature and reaction time on this procedure were investigated. Products were obtained in good yields using this mild and one-pot methodology

  特定于任务的次膦酸酯离子液体（IL-OPPh 2）被用作试剂，用于在微波辐射条件下通过乙炔二羧酸二（甲基或乙基）酯与酚类化合物的反应有效合成4-取代的香豆素。研究了亚膦酸酯离子液体的量，反应温度和反应时间等参数对该方法的影响。使用这种温和的一锅法在无溶剂条件下以高收率获得了产品。另外，离子液体循环测试表明它可以重复使用3次而不会损失其活性。
• CONVERSION OF IN SITU GENERATED STABILIZED PHOSPHORUS YLIDES TO CHROMENE DERIVATIVES IN SOLVENT-FREE CONDITIONS
  作者：Ali Ramazani、Liela Yousefi、Ebrahim Ahmadi、Ali Souldozi

  DOI：10.1080/10426500490463682

  日期：2004.7.1

  intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by phenols (1-hydroxynaphthalene, 2-hydroxynaphthalene, 4-bromophenol, 2-hydroxybenzaldehyde, and 5-bromo-2-hydroxyben- zaldehyde) leads to vinyltriphenylphosphonium salts, which undergo electrophilic substitution reaction with conjugate base to produce corresponding stabilized phosphorus ylides. Microwave was

  苯酚（1-羟基萘、2-羟基萘、4-溴苯酚、2-羟基苯甲醛和5-溴-2-羟基苯甲醛）质子化三苯基膦和二烷基乙炔二羧酸酯之间的反应产生的高反应性1:1中间体生成乙烯基三苯基鏻盐，与共轭碱发生亲电取代反应，生成相应的稳定磷叶立德。发现微波在固体催化剂存在下，在无溶剂条件下以 0.4 KW 的微波功率在 3 分钟内催化稳定的磷叶立德转化为色烯衍生物。
• “<i>β</i>-Cyclodextrin Nanoreactor” Catalyzed Synthesis of Coumarin Derivatives from <i>In-Situ</i> Generated Stabilized Phosphorus Ylides in Water
  作者：Ali Ramazani、Saman Ayoubi、Yavar Ahmadi、Hamideh Ahankar、Hamideh Aghahosseini、Sang Woo Joo

  DOI：10.1080/10426507.2015.1073285

  日期：2015.12.2

  Abstract A convenient one-pot synthesis of coumarin derivatives from the three-component reaction of triphenylphosphine, an acetylenic ester, and a phenol (1-naphthol, 2-naphthol and benzo[1,3]dioxol-5-ol) in the presence of a catalytic amount (4.5 mol%) of ß-cyclodextrin as a nanocatalyst and nanoreactor is reported. This methodology is of interest due to the use of water in the presence of this “ß-cyclodextrin

  图形摘要 摘要 通过三苯基膦、炔酸酯和苯酚（1-萘酚、2-萘酚和苯并 [1,3] 二氧六环-5-醇）的三组分反应，方便地一锅法合成香豆素衍生物。据报道，存在催化量 (4.5 mol%) 的 β-环糊精作为纳米催化剂和纳米反应器。由于在这种“β-环糊精纳米反应器”绿色反应系统的存在下使用了水，因此这种方法很有趣。
• Synthesis of Dimethyl 2-(2,4,6-Trimethylphenoxy)-3-triphenylphosphoniobutanedioate and its Application in Intramolecular Wittig Reactions
  作者：Issa Yavari、Farahnaz Nourmohammadian、Hamid R. Bijanzadeh

  DOI：10.1080/10426500211709

  日期：2002.5.1

  Protonation of the reactive 1:1 intermediate produced in the reaction between triphenylphosphine and dimethyl acetylenedicarboxylate by 2,4,6-trimethylphenol leads to a stable ylide in high yield, which is employed in intramolecular Wittig reactions.

  2,4,6-三甲基苯酚对三苯基膦和乙炔二甲酸二甲酯反应中产生的反应性 1:1 中间体进行质子化，以高产率得到稳定的叶立德，可用于分子内 Wittig 反应。
• MICROWAVE INDUCED SYNTHESIS OF COUMARINS FROM IN SITU GENERATED STABILIZED PHOSPHORUS YLIDES IN THE PRESENCE OF SILICA GEL POWDER IN SOLVENT-FREE CONDITIONS
  作者：Ali Ramazani、Ali Souldozi

  DOI：10.1080/10426500490422173

  日期：2004.3.1

  the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by phenols (1-hydroxynaphthalene, 2-hydroxynaphthalene and 4-bromophenol) leads to vinyltriphenylphosphonium salts, which undergo aromatic electrophilic substitution reaction with conjugate base to produce corresponding stabilized phosphorus ylides. Microwave was found to catalyze conversion of the stabilized phosphorus ylides

  苯酚（1-羟基萘、2-羟基萘和4-溴苯酚）对三苯基膦和二烷基乙炔二羧酸酯反应产生的高反应性1:1中间体进行质子化，生成乙烯基三苯基鏻盐，与共轭碱发生芳香族亲电取代反应，得到产生相应的稳定磷叶立德。发现微波在无溶剂条件下在硅胶粉末存在下催化稳定的磷叶立德转化为相应的香豆素。