methyl 2-oxo-2H-benzochromene-4-carboxylate | 23053-30-7

• 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 2-oxo-2H-benzochromene-4-carboxylate
• 英文别名: 2-oxo-2H-benzo[h]chromene-4-carboxylic acid methyl ester；methyl 2-oxo-2H-benzo[h]chromene-1-carboxylate；methyl 2-oxo-2H-benzo[h]chromene-4-carboxylate；methyl α-napthocoumarin-4-carboxylate；2-oxo-2H-benzo[h]chromene-4-carboxylic acid methyl ester；Methyl-2-oxo-2h-benzo[h]chromene-4-carboxylate；methyl 2-oxobenzo[h]chromene-4-carboxylate
• CAS: 23053-30-7
• 化学式: C₁₅H₁₀O₄
• 分子量: 254.242
• InChiKey: OGIGGXIEMFWUSL-UHFFFAOYSA-N

物化性质

• 熔点：
  162.0-162.2 °C
• 沸点：
  466.6±40.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

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

• 作为产物：
  描述：

  萘酚 在 manganese(II) sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 methyl 2-oxo-2H-benzochromene-4-carboxylate
  参考文献：
  名称：

  硫酸锰 (II) 粉末是在无溶剂条件下由原位生成的稳定磷叶立德合成香豆素的有效催化剂

  摘要：

  摘要 三苯基膦与二烷基乙炔二羧酸酯反应产生的高反应性 1:1 中间体，由苯酚（1-羟基萘、2-羟基萘和 4-溴苯酚）质子化生成乙烯基三苯基鏻盐，与共轭物发生芳香族亲电取代反应。生成相应的稳定磷叶立德。发现硫酸锰 (II) 粉末可在 90°C 的无溶剂条件下催化稳定的磷叶立德转化为香豆素，原因是 1 小时的高转化率。还发现在无溶剂条件下，在无溶剂条件下，在硫酸锰 (II) 粉末存在下，微波可在 1 分钟内以 1 KW 的微波功率催化相同的反应。

  DOI：

  10.1080/10426500590917407

文献信息

• 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。
• A New and Simple Synthesis of 3H-Benzo[f]chromen-3-one and 2H-Benzo[h]chromen-2-one Derivatives
  作者：Rahim Hekmatshoar、Yahya S. Beheshtiha、Monire Kheirkhah、Farnoosh Faridbod

  DOI：10.1007/s007060200039

  日期：2002.5.1

  Protonation of the highly reactive 1:1-intermediate produced in the reaction between triphenylphosphine and dimethyl acetylenedicarboxylate by naphthols lead to vinyl triphenylphosphonium salts which undergo an aromatic electrophilic substitution reaction with the conjugated base to produce the title compounds.
• Nicolaides, Demetrios N.; Adamopoulos, Spyros G.; Lefkaditis, Demetrios A., Journal of the Chemical Society. Perkin transactions I, 1990, # 7, p. 2127 - 2132
  作者：Nicolaides, Demetrios N.、Adamopoulos, Spyros G.、Lefkaditis, Demetrios A.、Litinas, Konstantinos E.

  DOI：——

  日期：——
• Silica Gel Catalyzed Conversion of Dialkyl 2-(1-Hydroxy-2-naphthyl)-3-(triphenylphosphoranylidene)butanedioates to Alkyl 2-Oxo-2 H -benzo[ h ]chromene-4-carboxylates in Solvent-Free Conditions
  作者：Ali Ramazani、Ali Souldozi

  DOI：10.1080/10426500307889

  日期：2003.6

  Protonation of the highly reactive 1:1 intermediates, produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylates, by 1-hydroxynaphthalene leads to vinyltriphenylphosphonium salts, which undergo aromatic electrophilic substitution reaction with conjugate base to produce dialkyl 2-(1-hydroxy-2-naphthyl)-3-(triphenylphosphanylidene)butanedioates. Silica gel was found to catalyze conversion of dialkyl 2-(1-hydroxy-2-naphthyl)-3-(triphenylphosphanylidene)butanedioates to alkyl 2-oxo-2H-benzo[h]chromene-4-carboxylates in solvent-free conditions at 80degreesC in fairly good yields.