acetoacetate diester of diethylene glycol | 24871-74-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: acetoacetate diester of diethylene glycol
• 英文别名: 3-oxapenta-1,5-diyl bis(3-oxobutanoate)；oxadiethylene di(3-oxobutanoate)；acetoacetic acid 3-oxa-pentane-1,5-diyl ester；bis-(2-acetoacetyloxy-ethyl)-ether；Bis-(2-acetoacetyloxy-aethyl)-aether；2-[2-(3-Oxobutanoyloxy)ethoxy]ethyl 3-oxobutanoate
• CAS: 24871-74-7
• 化学式: C₁₂H₁₈O₇
• 分子量: 274.271
• InChiKey: PQVYECRIZCVWGL-UHFFFAOYSA-N

物化性质

• 沸点：
  393.5±27.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  96
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  acetoacetate diester of diethylene glycol 在 [Ru(2,6-Cl2tpp)CO] 对甲苯磺酰叠氮 、 三乙胺 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 31.0h， 生成 (9Z)-1,4,7-trioxacycloundec-9-ene-8,11-dione
  参考文献：
  名称：

  Highly Selective Intra- and Intermolecular Coupling Reactions of Diazo Compounds to Form cis-Alkenes Using a Ruthenium Porphyrin Catalyst

  摘要：

  [Ru(2,6-Cl2TPP)(CO)] catalyzed intramolecular coupling reactions of bisdiazoacetates and intermolecular coupling reactions of monodiazoacetates to afford the coupling products in up to 76% and 93% yields, respectively. Only the cis isomers were obtained from the reactions. Employing such a ruthenium-catalyzed coupling reaction of a diazo compound as a key step allowed the synthesis of Patulolide B in 67% yield with a ratio of >40:1 against its trans isomer.

  DOI：

  10.1021/ol049626a
• 作为产物：
  描述：

  双乙烯酮 、 二乙二醇 在 sodium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以69%的产率得到acetoacetate diester of diethylene glycol
  参考文献：
  名称：

  Highly Selective Intra- and Intermolecular Coupling Reactions of Diazo Compounds to Form cis-Alkenes Using a Ruthenium Porphyrin Catalyst

  摘要：

  [Ru(2,6-Cl2TPP)(CO)] catalyzed intramolecular coupling reactions of bisdiazoacetates and intermolecular coupling reactions of monodiazoacetates to afford the coupling products in up to 76% and 93% yields, respectively. Only the cis isomers were obtained from the reactions. Employing such a ruthenium-catalyzed coupling reaction of a diazo compound as a key step allowed the synthesis of Patulolide B in 67% yield with a ratio of >40:1 against its trans isomer.

  DOI：

  10.1021/ol049626a

文献信息

• Synthesis and tuberculostatic activity of podands with a dihydropyrimidine fragment
  作者：E. S. Filatova、O. V. Fedorova、Yu. A. Titova、P. A. Slepukhin、M. A. Kravchenko、S. N. Skornyakov、G. L. Rusinov、V. N. Charushin

  DOI：10.1007/s11172-016-1462-4

  日期：2016.5

  toluene was optimized. A multi-component Biginelli reaction was used for the formation of the dihydropyrimidine ring on the ether matrix obtained. Tuberculostatic activity of dihydropyrimidine podands in the in vitro experiments against a laboratory strain H37Rv was studied. A combination of dihydropyrimidine and podand fragments imparts tuberculostatic activity to the compounds obtained, which noticeably

  一种通过加热时用 2,2,6-三甲基-4H-1,3-二恶英-4-one 乙酰乙酰化低聚（乙二醇）制备含 3-氧代丁酸酯的不同聚醚片段长度的 podands 的方法在甲苯中进行了优化。多组分Biginelli反应用于在获得的醚基质上形成二氢嘧啶环。研究了二氢嘧啶荚果在体外实验中对实验室菌株 H37Rv 的抗结核活性。二氢嘧啶和podand片段的组合赋予所获得的化合物抗结核活性，随着氧乙烯间隔物长度的增加，该活性显着​​增强。
• Hydrogel Prodrugs
  申请人：ASCENDIS PHARMA A/S

  公开号：US20150258205A1

  公开（公告）日：2015-09-17

  The present invention relates to a process for the preparation of a hydrogel and to a hydrogel obtainable by said process. The present invention further relates to a process for the preparation of a hydrogel-spacer conjugate, to a hydrogel-spacer conjugate obtainable by said process, to a process for the preparation of a carrier-linked prodrug and to carrier-linked prodrugs obtainable by said process, in particular to carrier-linked prodrugs that provide for a controlled or sustained release of a drug from a carrier. In addition, the invention relates to the use of the hydrogel for the preparation of a carrier-linked prodrug.

  本发明涉及一种制备水凝胶的方法，以及通过该方法可获得的水凝胶。本发明还涉及一种制备水凝胶-间隔物共轭物的方法，以及通过该方法可获得的水凝胶-间隔物共轭物，还涉及一种制备载体连结的前药的方法，以及通过该方法可获得的载体连结的前药，特别是提供了能够从载体中控制或持续释放药物的载体连结的前药。此外，本发明涉及使用水凝胶制备载体连结的前药。
• Synthesis and structure of functionalized podands containing 4,7-dihydrotetrazolo[1,5-а]pyrimidine ring. Differently substituted dihydropyrimidine podands
  作者：Elena S. Filatova、Olga V. Fedorova、Pavel A. Slepukhin、Gennady L. Rusinov、Valery N. Charushin

  DOI：10.1007/s10593-018-2373-0

  日期：2018.10

  5-а]dihydropyrimidine groups. Byproducts were isolated and identified as podands containing different substituents – one 4,7-dihydrotetrazolo[1,5-а]pyrimidine ring system and a free hydroxy group at the other terminus of the polyether chain. Analogous differently substituted podands, including one 3,4-dihydropyrimidine-2(1H)-thione moiety, were isolated from the reactions of 3-oxobutanoate-containing polyethers with

  在多磷酸存在下，含3-氧代丁酸酯的聚醚与苯甲醛和5-氨基四唑的反应被用于合成含有两个末端四唑并[1,5- α ]二氢嘧啶基团的豆荚。分离出副产物并将其鉴定为含有不同取代基的豆荚-一个4,7-二氢四唑并[1,5- α ]嘧啶环系统和在聚醚链另一端的自由羟基。从含3-氧代丁酸酯的聚醚与苯甲醛和硫脲的反应中分离出类似的不同取代的豆荚，包括一个3,4-二氢嘧啶-2（1 H）-硫酮部分。
• Synthesis of crown ethers containing the 3,5-di(alkoxycarbonyl)pyridine ring system by means of the Hantzsch condensation
  作者：T. J. van Bergen、Richard M. Kellogg

  DOI：10.1039/c39760000964

  日期：——

  The products obtained from reaction of ethyl acetoacetate with several (poly)ethyleneglycols undergo the Hantzsch condensation with ammonium carbonate and formaldehyde giving new crown ethers; transformations and properties of these new compounds are described.

  由乙酰乙酸乙酯与几种（聚）乙二醇反应制得的产物与碳酸铵和甲醛进行汉茨缩合反应，生成新的冠醚。描述了这些新化合物的转化和性质。
• Features of a multicomponent Biginelli reaction involving 3-oxobutanoyl-containing podands, aromatic aldehydes, and 1,2,4-triazol-3-amine
  作者：Elena S. Filatova、Olga V. Fedorova、Konstantin A. Chistyakov、Gennady L. Rusinov、Valery N. Charushin

  DOI：10.1007/s10593-020-02627-2

  日期：2020.1

  A reaction of 3-oxobutanoyl-containing podands with thiophene-2-carbaldehyde (or benzaldehyde) and 3-amino-1,2,4-triazole gave podands featuring a 4,7-dihydro[1,2,4]triazolo[1,5-а]pyrimidine motif. It was established that the process was accompanied by the formation of [4,3-а]-isomers, which occurred in a slight excess during the synthesis of a podand containing a phenyl group at position 7 and, on

  含3-氧代丁酸的豆荚与噻吩-2-甲醛（或苯甲醛）和3-氨基-1,2,4-三唑的反应得到具有4,7-二氢[1,2,4]三唑[1]的豆荚，5- а ]嘧啶基序。已经确定，该过程伴随有[4,3- α ]-异构体的形成，在合成在位置7处含有苯基的podand的过程中，该异构体略有过量，并且观察到作为在带有噻吩-2-基取代基的豆荚的合成过程中的次要产物。还检测到痕量的单取代的Podands，其中含有一个游离羟基以及三唑二氢嘧啶药效团。