ethyl 4,5-dioxo-2-phenyl-4,5-dihydrofuran-3-carboxylate | 134567-92-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl 4,5-dioxo-2-phenyl-4,5-dihydrofuran-3-carboxylate
• 英文别名: 4-ethoxycarbonyl-5-phenyl-2,3-dihydrofuran-2,3-dione；4-(ethoxycarbonyl)-5-phenyl-2,3-furandione；ethyl 4,5-dioxo-2-phenylfuran-3-carboxylate
• CAS: 134567-92-3
• 化学式: C₁₃H₁₀O₅
• 分子量: 246.219
• InChiKey: RQJKFUUNGJSOID-UHFFFAOYSA-N

物化性质

• 沸点：
  381.9±52.0 °C(Predicted)
• 密度：
  1.365±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4,5-dioxo-2-phenyl-4,5-dihydrofuran-3-carboxylate 500.0 ℃ 、0.11 Pa 条件下， 反应 5.0h， 以65%的产率得到苯甲酰乙酸乙酯
  参考文献：
  名称：

  Reactions of cyclic oxalyl compounds XXXIX. Reactions of 4-Ethoxycarbonyl-5-phenyl-2,3-dihydrofuran-2,3-dione with heterocumulenes andSchiff bases

  摘要：

  Furan-2,3-dione 1 reacts with arylisocyanates to the corresponding pyrrol-2,3-diones 2, whereas conversion with diisopropylcarbodiimide affords the oxazepin-6,7-dione derivative 3 in 68% yield. 1,3-Oxazines 5, 6, and 7 were obtained by thermolysis of 1 in boiling xylene in presence of arylisocyanates, diphenylketen-p-tolylimine, and Schiff bases, most likely by trapping the alpha-oxoketene intermediate 4. Preparative flash vakuum pyrolysis (FVP) of 1 and 2b gave 8 and 9, respectively.

  DOI：

  10.1007/bf00810774
• 作为产物：
  描述：

  苯乙酮 在 sodium hydride 、 magnesium chloride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.0h， 生成 ethyl 4,5-dioxo-2-phenyl-4,5-dihydrofuran-3-carboxylate
  参考文献：
  名称：

  以吡咯为原料一步一步无催化剂合成吡咯利嗪酮和吡咯利嗪并[1,2-a]pyrrolizin-5-one骨架

  摘要：

  1 H-吡咯与内酯型 2,3-呋喃二酮衍生物在无水乙醚中于室温下在无催化剂的情况下一步反应生成一系列吡咯嗪酮衍生物（最重要的生物碱骨架之一）。获得了具有各种取代基的吡咯嗪酮衍生物，例如苯基、取代的苯基、噻吩基、三氟甲基、萘基、联苯基、酯或草酸酯。等摩尔的吡咯反应生成吡咯嗪酮，而过量的吡咯生成吡咯并[1,2- a]pyrrolizin-5-ones 含有以前没有报道过的骨架。纯化分子的收率高达 91%。以克规模进行一次环化过程，产生 0.952 g (71%) 的相应产物。

  DOI：

  10.1055/a-2006-4390

文献信息

• Synthesis and some reactions of 4-(ethoxycarbonyl)-1,5-diphenyl-1<i>H</i>-pyrazole-3-carboxylic acid
  作者：Ahmet Şener、İshak Bildirici、İsrafil Tozlu、Hasan Genç、Kadir Arısoy

  DOI：10.1002/jhet.5570440516

  日期：2007.9

  1,5-Diphenyl-1H-pyrazole-3,4-dicarboxylic acid-4-ethyl ester 2, obtained from the 4-ethoxycarbonyl-5-phenyl-2,3-furandione 1 and N-benzylidene-N′-phenyl hydrazine, was converted via reactions of its acid chloride 3 with various alcohols or N-nucleophiles into the corresponding ester 5 or amide derivatives 6, respectively. In addition, 2 was decarboxylated to give ethyl 1,5-diphenylpyrazole-4-carboxylate

  1,5-二苯基-1- ħ吡唑-3,4-二甲酸-4-乙基酯2，从4-乙氧羰基-5-苯基-2,3-呋喃二酮获得1和Ñ -benzylidene- Ñ ' -苯基肼通过其酰氯3与各种醇或N-亲核试剂的反应分别转化为相应的酯5或酰胺衍生物6。另外，将2脱羧得到1，5-二苯基吡唑-4-羧酸乙酯4。腈7衍生物的2也通过脱水而获得图6a在SOCl 2和DMF的混合物中。2与水合肼的环缩合反应导致吡唑并[3,4- d ]哒嗪-4,7-二酮8的形成，而3与无水肼的反应则提供了一种新的双吡唑衍生物9。
• Preparation of novel pyrrol-2-one derivatives via an effective synthesis of new oxazole scaffold
  作者：İbrahim Evren Kibriz、Mustafa Saçmaci、Ertan Şahin、İsmail Yildirim

  DOI：10.1016/j.tet.2017.01.046

  日期：2017.4

  A convenient procedure for the preparation of oxazole and pyrrole derivatives is described. 2-Amino-1,3-oxazol-2-ones 3a,b were first synthesized from the cyclocondensation reactions of cyanamide (2) with 4-ethoxycarbonyl-5-aryl-2,3-furandione 1a,b, and then new pyrrol-2-ones 5 were synthesized from the reaction of the compounds 3 with various aromatic amines 4.

  描述了一种方便的制备恶唑和吡咯衍生物的方法。首先从氰胺（2）与4-乙氧基羰基-5-芳基-2,3-呋喃二酮1a，b的环缩合反应合成2-氨基-1,3-恶唑-2-酮3a，b，然后合成新的吡咯由化合物3与各种芳族胺4的反应合成了-2-酮5。
• Reactions of cyclic oxalyl compounds — 38. New isoindigoide dyes from heterocyclic 2,3-diones — Synthesis and thermal rearrangement
  作者：G. Kollenz、G. Penn、R. Theuer、W.M.F. Fabian、H.A. Abd El-Nabi、Xiong Zhang、K. Peters、E.-M. Peters、H.G. von Schnering

  DOI：10.1016/0040-4020(96)00173-1

  日期：1996.4

  The heterocyclic 2,3-diones 1 and 11 together with Lawesson reagent (LR) afford novel isoindigoide dyes 4 and 12, respectively. 4a can thermally be isomerized into the pyrano[4,3-c]pyrane 6, accompanied by a significant hypsochromic shift which was corroborated by quantum chemical calculations. The phoshporanylidene derivative 13 was obtained via Wittig reaction of 1. All structural assignments were

  杂环2，3-二酮1和11以及Lawesson试剂（LR）分别提供了新型的靛蓝染料4和12。4a可以热异构为吡喃并[4,3-c]吡喃6，伴随着显着的变色转变，这通过量子化学计算得到了证实。通过1的Wittig反应获得了磷丝亚基衍生物13。所有结构分配均基于4a和13的X射线研究。
• Synthesis of some pyrazole-3-carboxylic acid-hydrazide and pyrazolopyridazine compounds
  作者：İ Özer İlhan、Emin Saripinar、Yunus Akçamur

  DOI：10.1002/jhet.5570420117

  日期：2005.1

  Furan-2,3-diones 1a-c react with various hydrazines 2a-c under different conditions to yield the pyrazole-3-carboxylic acid-hydrazide 3a-d. Cyclocondensation reactions of 1a or 7 with phenylhydrazine lead to derivatives of pyrazolo[3,4-d]pyridazinones 6 and 8, respectively. The structures of all products were confirmed by elemental analysis, IR, 1H- and 13C-NMR spectroscopic measurements.

  呋喃-2，3-二酮1a-c在不同条件下与各种肼2a -c反应，得到吡唑-3-羧酸-酰肼3a-d。1a或7与苯肼的环缩合反应分别生成吡唑并[3,4- d ]哒嗪酮6和8的衍生物。所有产品的结构均通过元素分析，IR，1 H-和13 C-NMR光谱测定证实。
• Efficient synthesis of some oxalacetic acid and pyruvic acid derivatives from the reactions of 2,3-furandiones with 2-phenylindole
  作者：Ahmet Şener、Nurettin Mengeş、Mehmet Akkurt、Selvi Karaca、Orhan Büyükgüngör

  DOI：10.1016/j.tetlet.2008.02.118

  日期：2008.4

  Oxalacetic acid and pyruvic acid derivatives have been synthesized efficiently in high yields by the treatment of 4-ethoxycarbonyl-5-phenyl-2,3-furandione and 4-benzoyl-5-phenyl-2,3-furandione with 2-phenylindole at room temperature and converted to simple derivatives such as an ester or a hydrazone.

  通过在室温下用2-苯基吲哚处理4-乙氧基羰基-5-苯基-2，3-呋喃二酮和4-苯甲酰基-5-苯基-2，3-呋喃二酮，可以高产率高效地合成草酰乙酸和丙酮酸衍生物。并转化为简单的衍生物，例如酯或a。