diethyl 3,3'-(1,3-phenylene)bis(3-oxopropanoate) | 1120350-26-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diethyl 3,3'-(1,3-phenylene)bis(3-oxopropanoate)
• 英文别名: ,3-bis(1-oxo-3-ethoxycarbonylpropyl) benzene；diethyl isophthaloyldiacetate；Diethyl 3,3'-(1,3-phenylene)bis(3-oxo-propanoate)；ethyl 3-[3-(3-ethoxy-3-oxopropanoyl)phenyl]-3-oxopropanoate
• CAS: 1120350-26-6
• 化学式: C₁₆H₁₈O₆
• 分子量: 306.315
• InChiKey: ZBAUVOHIKBBOCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 3,3'-(1,3-phenylene)bis(3-oxopropanoate) 在 盐酸 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 6.33h， 生成 3,3'-(benzene-1,3-diyl)bis(4-hydroxyimino-1-methyl-1H-pyrazol-5-one)
  参考文献：
  名称：

  苯撑双吡唑酮和亚硝化衍生物的合成与表征

  摘要：

  通过两个芳香族β-二酮二酯与甲基，2-羟乙基和苯肼的缩合反应制得苯二甲双吡唑酮衍生物。吡唑啉酮环通过其C-3连接至中心苯环，使C-4游离以进一步衍生化。因此，尽管它们的溶解度低，但仍成功地将它们以高收率成功地亚硝化，从而提供了新的螯合二肟。

  DOI：

  10.1002/jhet.1843
• 作为产物：
  描述：

  在 硫酸 作用下， 以 乙醇 、 甲苯 为溶剂， 以73%的产率得到diethyl 3,3'-(1,3-phenylene)bis(3-oxopropanoate)
  参考文献：
  名称：

  Convenient synthesis and characterization of molecules containing multiple β-keto ester units

  摘要：

  Three compounds containing two beta-keto ester units and one containing three were obtained in good yields from sebacyl, terepthaloyl, isophthaloyl, and trimesoyl chlorides. In this one pot procedure the acid chlorides were first treated with ethyl acetoacetate and barium oxide and then with ethyl alcohol. The aliphatic ester exists mainly as keto ester with a very small amount of the enol tautomer. In the case of aromatic esters, all possible tautomers were found in considerable concentrations in deuterochloroform solution. Theoretical chemical shifts were estimated from GIAO/WP04/aug-cc-pVDZ/SCRF calculations, for a probable signal assignation for the corresponding tautomeric species. Our theoretical results are in agreement with experimental findings and account for negligible stability differences between the tautomers of each aromatic compound. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.025

文献信息

• Three-component condensation of diethyl isophthaloyldiacetate, aromatic aldehyde, and urea as a new method for the synthesis of 1,3-bis(2-oxo-1,2,3,4-tetrahydropyrimidin-6-yl)benzenes
  作者：V. A. Mamedov、S. V. Vdovina、E. I. Vorkunova、L. V. Mustakimova、A. F. Saifina、A. T. Gubaidullin、I. Kh. Rizvanov、Ya. A. Levin、I. A. Litvinov

  DOI：10.1007/s11172-008-0161-1

  日期：2008.6

  Condensation of diethyl isophthaloyldiacetate, aromatic aldehyde, and urea in the presence of Me3SiCl proceeds efficiently and faster than in the absence of the latter to form 1,3-bis(2-oxo-1,2,3,4-tetrahydropyrimidin-6-yl)benzene derivatives capable to give inclusion complexes with DMF.

  在 Me3SiCl 存在下，间苯二甲酰二乙酸二乙酯、芳香醛和尿素的缩合反应比没有后者更有效、更快地进行，形成 1,3-双（2-氧代-1,2,3,4-四氢嘧啶-6-基)苯衍生物能够与 DMF 形成包合物。
• Chloro(trimethyl)silane-catalyzed three-component condensation of diethyl 3,3′-(1,3-phenylene)bis(3-oxo-propanoate) with aromatic aldehyde and urea. New synthesis of diethyl 4,4′-(1,3-phenylene)bis(2-oxo-1,2,3,6-tetrahydropyrimidine-5-carboxylates)
  作者：S. V. Vdovina、L. V. Mustakimova、V. A. Mamedov

  DOI：10.1134/s1070428008040325

  日期：2008.4
• Convenient synthesis and characterization of molecules containing multiple β-keto ester units
  作者：Julio Belmar、Leandro Ortiz、Denis Ramírez、Fabiola Fuentes、María Parra、Verónica A. Jiménez、Claudio A. Jiménez

  DOI：10.1016/j.tetlet.2012.07.025

  日期：2012.9

  Three compounds containing two beta-keto ester units and one containing three were obtained in good yields from sebacyl, terepthaloyl, isophthaloyl, and trimesoyl chlorides. In this one pot procedure the acid chlorides were first treated with ethyl acetoacetate and barium oxide and then with ethyl alcohol. The aliphatic ester exists mainly as keto ester with a very small amount of the enol tautomer. In the case of aromatic esters, all possible tautomers were found in considerable concentrations in deuterochloroform solution. Theoretical chemical shifts were estimated from GIAO/WP04/aug-cc-pVDZ/SCRF calculations, for a probable signal assignation for the corresponding tautomeric species. Our theoretical results are in agreement with experimental findings and account for negligible stability differences between the tautomers of each aromatic compound. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis and Characterization of Phenylene-<i>bis</i>-pyrazolones and Nitrosation Derivatives
  作者：J. Belmar、L. Ortiz、J. Quezada、M. Parra、C. A. Jiménez

  DOI：10.1002/jhet.1843

  日期：2014.8

  Phenylene bis-pyrazolone derivatives were obtained by condensation of two aromatic β-diketo diesters with methyl-, 2-hydroxyethyl- and phenylhydrazines. The pyrazolone rings are connected to the central benzene ring by their C-3, leaving C-4 free for further derivatization. Thus, and despite their low solubility, these compounds were successfully nitrosated in good yield providing new chelating dioximes

  通过两个芳香族β-二酮二酯与甲基，2-羟乙基和苯肼的缩合反应制得苯二甲双吡唑酮衍生物。吡唑啉酮环通过其C-3连接至中心苯环，使C-4游离以进一步衍生化。因此，尽管它们的溶解度低，但仍成功地将它们以高收率成功地亚硝化，从而提供了新的螯合二肟。