6-(4-chlorophenyl)-4-oxo-4H-pyrane-2-carboxylic acid | 76781-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-(4-chlorophenyl)-4-oxo-4H-pyrane-2-carboxylic acid
• 英文别名: 6-(4-chlorophenyl)-4-oxo-4H-pyran-2-carboxylic acid；6-(4-chlorophenyl)-4-oxopyran-2-carboxylic acid
• CAS: 76781-93-6
• 化学式: C₁₂H₇ClO₄
• 分子量: 250.638
• InChiKey: UTOVNCUJVMBPQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(4-chlorophenyl)-4-oxo-4H-pyrane-2-carboxylic acid 在 四氯化碳 、 三苯基膦 作用下， 生成 6-(4-Chloro-phenyl)-4-oxo-4H-pyran-2-carbonyl chloride
  参考文献：
  名称：

  Studies on antiallergic agents. I. Phenyl-substituted heterocycles with a 5-tetrazolyl or N-(5-tetrazolyl)carbamoyl group.

  摘要：

  合成了一系列以 5-四唑基或 N-(5-四唑基)氨基甲酰基为酸性分子的苯基取代的吡喃、吡啶和嘧啶。这些化合物在大鼠口服后通过被动皮肤过敏试验（PCA）测试其抗过敏活性。合成的化合物包括发现 N-（5-四唑基）-6-苯基吡啶-2-甲酰胺（53、54 和 55）具有显著的高效力。

  DOI：

  10.1248/cpb.30.4314
• 作为产物：
  描述：

  ethyl 5-(4-chlorobenzoyl)-4-oxo-4H-pyrane-2-carboxylate 在 盐酸 、 水 作用下， 反应 8.0h， 以85%的产率得到6-(4-chlorophenyl)-4-oxo-4H-pyrane-2-carboxylic acid
  参考文献：
  名称：

  通过甲酰基化重排和开环/闭环序列，由5-芳酰基-2-碳乙氧基-4-吡喃酮合成6-芳基和5-芳基甲酸。

  摘要：

  1-芳基-2-（二甲基氨基亚甲基）丁烷-1,3-二酮与草酸二乙酯在氢化钠存在下于THF中反应，得到5-芳酰基-4-氧代-4 H-吡喃-2-羧酸乙酯通过酸催化的甲酰基化重排以高收率获得了4-氧代-6-芳基-4 H-吡喃-2-羧酸（6-芳基马来酸）。通过开环/闭环顺序，通过5-芳酰基-2-碳乙氧基-4-吡喃酮的反应，制备5-芳基-4-氧代-4 H-吡喃-2-羧酸（5-芳酰基马甲酸）用哌啶随后进行碱性水解和酸化。

  DOI：

  10.1016/j.tetlet.2013.11.066

文献信息

• Synthesis of 6-aryl- and 5-aroylcomanic acids from 5-aroyl-2-carbethoxy-4-pyrones via a deformylative rearrangement and ring-opening/ring-closure sequence
  作者：Dmitrii L. Obydennov、Gerd-Volker Röschenthaler、Vyacheslav Ya. Sosnovskikh

  DOI：10.1016/j.tetlet.2013.11.066

  日期：2014.1

  oxalate in the presence of sodium hydride in THF gave ethyl 5-aroyl-4-oxo-4H-pyran-2-carboxylates, from which 4-oxo-6-aryl-4H-pyran-2-carboxylic acids (6-arylcomanic acids) were obtained in high yields via acid-catalyzed deformylative rearrangement. 5-Aroyl-4-oxo-4H-pyran-2-carboxylic acids (5-aroylcomanic acids) were prepared via а ring-opening/ring-closure sequence by the reaction of 5-aroyl-2-carbethoxy-4-pyrones

  1-芳基-2-（二甲基氨基亚甲基）丁烷-1,3-二酮与草酸二乙酯在氢化钠存在下于THF中反应，得到5-芳酰基-4-氧代-4 H-吡喃-2-羧酸乙酯通过酸催化的甲酰基化重排以高收率获得了4-氧代-6-芳基-4 H-吡喃-2-羧酸（6-芳基马来酸）。通过开环/闭环顺序，通过5-芳酰基-2-碳乙氧基-4-吡喃酮的反应，制备5-芳基-4-氧代-4 H-吡喃-2-羧酸（5-芳酰基马甲酸）用哌啶随后进行碱性水解和酸化。
• Reactions of 4-Pyrones with Azomethine Ylides as a Chemo­selective Method for the Construction of Multisubstituted Pyrano[2,3-c]pyrrolidines
  作者：Dmitrii L. Obydennov、Vyacheslav D. Steben’kov、Konstantin L. Obydennov、Sergey A. Usachev、Vladimir S. Moshkin、Vyacheslav Y. Sosnovskikh

  DOI：10.1055/s-0040-1706032

  日期：2021.8

  nonstabilized azomethine ylides to form pyrano[2,3-c]pyrrolidines in moderate to good yields. The reaction proceeds chemoselectively as a 1,3-dipolar cycloaddition of the azomethine ylide at the carbon–carbon double bond of the pyrone activated by the electron-withdrawing substituent. The reactivity of 4-pyrones toward azomethine ylides was rationalized by computational studies with the use of reactivity

  带有给电子和吸电子基团的4-吡喃酮与不稳定的偶氮甲亚胺基化物反应，以中等至良好的产率形成吡喃并[2,3- c ]吡咯烷。该反应作为由吸电子取代基活化的吡喃酮的碳-碳双键上的偶氮甲基内叶的1,3-偶极环加成反应而化学选择性地进行。通过使用反应性指数的计算研究，使4-吡喃酮对偶氮甲亚胺的反应性合理化。吡喃并[2，3- c ]吡咯烷部分可以被修饰，例如通过在肼的作用下的开环转化以提供吡唑基取代的吡咯烷。
• 6-Substituted pyranone compounds and their use as pharmaceuticals
  申请人：Lilly Industries Limited

  公开号：US04304728A1

  公开（公告）日：1981-12-08

  Compounds are described of the formula ##STR1## in which R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano, 5-tetrazolyl or R.sup.6, where R.sup.5 is hydrogen or C.sub.1-8 alkyl and R.sup.6 is phenyl or naphthyl, the phenyl or naphthyl group being optionally substituted by one or more group selected from halogen, C.sub.1-6 alkyl, C.sub.1-4 alkoxy, hydroxy, benzyloxy, nitro, trifluoromethyl, carboxyl, C.sub.1-4 alkylsulphinyl, C.sub.1-4 alkylsulphonyl, N(R.sup.5).sub.2, NHCOR.sup.5 and SR.sup.5 ; R.sup.2 is R.sup.6 or --CH.dbd.CH--R.sup.6 when R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano or 5-tetrazolyl, or R.sup.2 is --CH.dbd.CH--R.sup.6 when R.sup.1 is R.sup.6 ; R.sup.3 is hydrogen, C.sub.1-6 alkyl, halogen, hydroxy or --OCH.sub.2 R.sup.6 ; and R.sup.4 is hydrogen, C.sub.1-6 alkyl or halogen; and salts thereof. The compounds have pharmaceutical properties and in particular are useful in the treatment of immediate hypersensitivity conditions such as asthma.

  该化合物的结构式为##STR1##其中R.sup.1为COOR.sup.5、CONHR.sup.5、氰基、5-四唑基或R.sup.6，其中R.sup.5为氢或C.sub.1-8烷基，R.sup.6为苯基或萘基，苯基或萘基可以选择性地被一个或多个取代基取代，所述取代基选自卤素、C.sub.1-6烷基、C.sub.1-4烷氧基、羟基、苄氧基、硝基、三氟甲基、羧基、C.sub.1-4烷基磺基、C.sub.1-4烷基磺酰基、N(R.sup.5).sub.2、NHCOR.sup.5和SR.sup.5；R.sup.2为R.sup.6或--CH.dbd.CH--R.sup.6，当R.sup.1为COOR.sup.5、CONHR.sup.5、氰基或5-四唑基时，或者当R.sup.1为R.sup.6时，R.sup.2为--CH.dbd.CH--R.sup.6；R.sup.3为氢、C.sub.1-6烷基、卤素、羟基或--OCH.sub.2 R.sup.6；R.sup.4为氢、C.sub.1-6烷基或卤素；以及它们的盐。这些化合物具有药理特性，特别是在治疗哮喘等即时超敏症状方面具有用途。
• The reaction of 6-substituted 4-pyrone-2-carboxylic acids with o-phenylenediamine. Synthesis and structure of 3-(1H-1,5-benzodiazepin-2(3Н)-ylidenemethyl)quinoxalin-2(1H)-ones
  作者：Dmitrii L. Obydennov、Vyacheslav Ya. Sosnovskikh

  DOI：10.1007/s10593-015-1696-3

  日期：2015.3

  [GRAPHICS]6-Aryl(alkyl)-4-pyrone-2-carboxylic acids upon refluxing in n-BuOH react with two equivalents of.-phenylenediamine, giving 26-85% yields of 3-(1H-1,5-benzodiazepin-2(3H)-ylidenemethyl)quinoxalin-2(1H)-ones, which exist in two tautomeric forms. The direction of the initial nucleophilic attack on the pyrone ring and the tautomeric composition of the obtained products is mainly determined by the substituent at the.-6 atom. Quantum-chemical calculations were used to estimate the stability of tautomers in the gas phase.
• HONMA, YASUSHI;SEKINE, YASUO;HASHIYAMA, TOMIKI;TAKEDA, MIKIO;ONO, YASUTOS+, CHEM. AND PHARM. BULL., 1982, 30, N 12, 4314-4324
  作者：HONMA, YASUSHI、SEKINE, YASUO、HASHIYAMA, TOMIKI、TAKEDA, MIKIO、ONO, YASUTOS+

  DOI：——

  日期：——