sodium ethyl acetoacetate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: sodium ethyl acetoacetate
• 英文别名: ethyl sodioacetoacetate；acetoacetic acid ethyl ester; sodium salt；Acetessigsaeure-aethylester (Natrium-Verbindung)
• 化学式: C₆H₉NaO₃
• 分子量: 152.125
• InChiKey: FAIIZDNAUXAOGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  27.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  sodium ethyl acetoacetate 在 乙醇 、 氨 作用下， 生成 2,5-bis-(1-imino-ethyl)-adipic acid diethyl ester
  参考文献：
  名称：

  Perkin, Journal of the Chemical Society, 1890, vol. 57, p. 221

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰乙酸乙酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 sodium ethyl acetoacetate
  参考文献：
  名称：

  Effect of polymer attachment on the equilibrium acidity of an organotransition metal hydride and an organic carboxylic acid. Synthesis and properties of a polymer-supported metal anion

  摘要：

  DOI：

  10.1021/ja00536a018

文献信息

• Facile One-pot Syntheses of Amidines and Enamines from Oximes via Beckmann Rearrangement Using Trifluoromethansulfonic Anhydride
  作者：Tomofumi Takuwa、Tomofumi Minowa、Jim Yoshitaka Onishi、Teruaki Mukaiyama

  DOI：10.1246/cl.2004.322

  日期：2004.3

  Facile one-pot syntheses of amidines and enamines were achieved by trapping carbocation intermediates that were formed by Beckmann rearrangement of oximes with amines and carbon nucleophiles, respectively, under mild conditions.

  通过在温和条件下分别利用胺和碳亲核试剂捕获由肟经贝克曼重排形成的碳正离子中间体，实现了酰亚胺和烯胺的简易一锅法合成。
• Facile One-Pot Syntheses of Amidines and Enamines from Oximes via Beckmann Rearrangement Using Trifluoromethanesulfonic Anhydride
  作者：Tomofumi Takuwa、Tomofumi Minowa、Jim Yoshitaka Onishi、Teruaki Mukaiyama

  DOI：10.1246/bcsj.77.1717

  日期：2004.9

  Iminocarbocation intermediates were in situ-generated by treating various oximes with trifluoromethanesulfonic anhydride (Tf2O) in the presence of triethylamine in toluene and nucleophilic trapping with amines or sodium enolates under mild conditions afforded the corresponding amidines and enamines. Some of the thus-obtained enamines were converted to 2-substituted 4-oxo-3-quinolinecarboxylic acid derivatives by subsequent intramolecular Friedel–Crafts acylation.

  通过将各种肟在甲苯中与三氟甲磺酸酐（Tf2O）和三乙胺反应，原位生成亚胺碳正中间体，并在温和条件下用胺或烯醇钠捕捉，得到相应的脒和烯胺。部分获得的烯胺随后通过分子内 Friedel-Crafts 酰基化反应转化为 2-取代的 4-氧代-3-喹啉羧酸衍生物。
• Preparation and Reactivities of (η³-1- and 2-Trimethylsiloxyallyl)Fe(CO)₂NO Complexes. Intermediates Functioning as Equivalents of β- and α-Acyl Carbocations and Acyl Carbanions
  作者：Keiji Itoh、Saburo Nakanishi、Yoshio Otsuji

  DOI：10.1246/bcsj.64.2965

  日期：1991.10

  (η3-1- and 2-Trimethylsiloxyallyl)Fe(CO)2NO complexes were prepared by the reaction of the corresponding siloxyallylic halides with Bu4N[Fe(CO)3NO]. These complexes reacted with both of carbon nucleophiles and carbon electrophiles preferentially at the less hindered sites of the allylic ligands. In these reactions, (η3-1-trimethylsiloxyallyl)Fe(CO)2NO complexes served as synthetically equivalent synthons

  (η3-1-和2-三甲基甲硅烷氧基烯丙基)Fe(CO)2NO配合物是通过相应的甲硅烷氧基烯丙基卤化物与Bu4N[Fe(CO)3NO]反应制备的。这些配合物优先与碳亲核试剂和碳亲电试剂在烯丙基配体的受阻较小的位点反应。在这些反应中，(η3-1-三甲基甲硅烷氧基烯丙基)Fe(CO)2NO 配合物作为 β-酰基碳正离子和 j8-酰基碳负离子和 (η3-2-三甲基甲硅烷氧基烯丙基)Fe(CO)2NO 配合物的合成等效合成子α-酰基碳正离子和α-酰基碳负离子。描述了反应的立体化学过程。
• Polyene cyclizations using mercury (II) triflate-N,N-dimethylaniline complex - participation by internal nucleophiles
  作者：Aravamudan S. Gopalan、Robert Prieto、Britta Mueller、David Peters

  DOI：10.1016/s0040-4039(00)91704-0

  日期：1992.3

  The cyclization of a number of functionalized polyenes with mercuric triflate - N,N-dimethylaniline complex (Nishizawa's reagent) to give bicyclic or tricyclic products has been studied. Suitably positioned internal nucleophiles, such as carbonyl, hydroxy and β-ketoester groups were found to participate to varying extent, in the termination of these cyclizations.

  已经研究了使用三氟甲磺酸汞-N，N-二甲基苯胺络合物（西泽试剂）将许多官能化多烯环化以生成双环或三环产物的方法。发现合适定位的内部亲核试剂，例如羰基，羟基和β-酮酸酯基团在这些环化的终止中以不同程度参与。
• Photochemical synthesis of a 4,5-dihydrofuroazetidinone, a novel β-lactam system
  作者：Donato Donati、Stefania Fusi、Fabio Ponticelli

  DOI：10.1016/j.tetlet.2003.10.079

  日期：2003.12

  2,4-Dimethyl-3-phenylisoxazole anhydrobases were easily prepared from the corresponding 5-chloroisoxazolium trifluoromethanesulfonate and carbon anions of 1,3-dioxo compounds in the presence of triethylamine. Photorearrangement of 2-(2,4-dimethyl-3-phenyl-2H-isoxazol-5-ylidene)malonic acid diethyl ester gave a 4,5-dihydrofuroazetidinone in good yield.

  在三乙胺存在下，由相应的5-氯异恶唑三氟甲烷磺酸盐和1,3-二氧杂化合物的碳阴离子可轻松制备2,4-二甲基-3-苯基异恶唑脱水碱。2-（2,4-二甲基-3-苯基-2的Photorearrangement ħ -异恶唑-5-亚基）丙二酸二乙酯，得到收率良好4,5- dihydrofuroazetidinone。