2H-chromene-4-carboxylic acid methyl ester | 519157-15-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2H-chromene-4-carboxylic acid methyl ester
• 英文别名: methyl 2H-chromene-4-carboxylate
• CAS: 519157-15-4
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: XVNQBERZTJJYMF-UHFFFAOYSA-N

物化性质

• 沸点：
  317.0±42.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2H-chromene-4-carboxylic acid methyl ester 在 palladium 10% on activated carbon 氢气 作用下， 以 乙酸乙酯 为溶剂， 以100%的产率得到methyl chroman-4-carboxylate
  参考文献：
  名称：

  Fused bicyclic carboxamide derivatives and methods of their use

  摘要：

  揭示了融合的双环羧酰胺衍生物。还公开了含有这些化合物的药物组合物以及它们的使用方法。

  公开号：

  US20050054630A1
• 作为产物：
  描述：

  4-phenoxy-but-2-ynoic acid methyl ester 在 palladium diacetate 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以59%的产率得到2H-chromene-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Pt^IV-Catalyzed Cyclization of Arene−Alkyne Substrates via Intramolecular Electrophilic Hydroarylation

  摘要：

  [GRAPHICS]We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety.

  DOI：

  10.1021/ol034177k

文献信息

• Pt(IV)-catalyzed cyclization of arene–alkyne substrates via C–H bond functionalization
  作者：Stefan J Pastine、So Won Youn、Dalibor Sames

  DOI：10.1016/j.tet.2003.05.003

  日期：2003.11

  We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety. PtCl4 is compatible with both terminal and disubstituted alkynes, as well as with various functionalities on the arene ring, including methyl, methoxyl, hydroxyl, protected amine, and halide. (C) 2003 Elsevier Ltd. All rights reserved.
• The first intramolecular Heck–Matsuda reaction and its application in the syntheses of benzofurans and indoles
  作者：Fernanda A. Siqueira、Jason G. Taylor、Carlos Roque D. Correia

  DOI：10.1016/j.tetlet.2010.02.011

  日期：2010.4

  In this Letter, we report, for the first time, the development of an efficient method for the intramolecular Heck reaction of arenediazonium salts in the synthesis of benzofuran and indole derivatives. In addition, this methodology allowed the synthesis of a series of dihydrobenzofuran acetic acid derivatives via a domino Heck-Matsuda coupling-carbonylation reaction. (c) 2010 Elsevier Ltd. All rights reserved.
• US7034051B2
  申请人：——

  公开号：US7034051B2

  公开（公告）日：2006-04-25
• [EN] FUSED BICYCLIC CARBOXAMIDE DERIVATIVES AND METHODS OF THEIR USE<br/>[FR] DERIVES DE CARBOXAMIDES BICYCLIQUES FUSIONNES ET LEURS PROCEDES D'UTILISATION
  申请人：ADOLOR CORP

  公开号：WO2005023799A1

  公开（公告）日：2005-03-17

  Fused bicyclic carboxamide derivatives of the general formula (I) are disclosed. Pharmaceutical compositions containing the compounds and methods for their use, inter alia, in treating and/or preventing pain, pruritus, and gastrointestinal disorders are also disclosed.
• Fused bicyclic carboxamide derivatives and methods of their use
  申请人：Dolle E. Roland

  公开号：US20050054630A1

  公开（公告）日：2005-03-10

  Fused bicyclic carboxamide derivatives are disclosed. Pharmaceutical compositions containing the compounds and methods for their use are also disclosed.

  揭示了融合的双环羧酰胺衍生物。还公开了含有这些化合物的药物组合物以及它们的使用方法。