ethyl 3-methyl-2,4-dioxo-4-phenylbutanoate lithium salt | 221385-22-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 3-methyl-2,4-dioxo-4-phenylbutanoate lithium salt
• 英文别名: lithium salt of ethyl 2,4-dioxo-3-methyl-4-phenylbutanoate；3-methyl-4-phenyl-2,4-dioxobutanoic acid ethyl ester lithium salt；Lithium;ethyl 3-methyl-2,4-dioxo-4-phenylbutanoate
• CAS: 221385-22-4
• 化学式: C₁₃H₁₃O₄*Li
• 分子量: 240.185
• InChiKey: PBXYNBVUHRDCEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-methyl-2,4-dioxo-4-phenylbutanoate lithium salt 在 硫酸 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 20.0h， 生成 1-(2,4-dichlorophenyl)-4-methyl-5-phenyl-1H-pyrazole-3-carboxylic acid
  参考文献：
  名称：

  1,5-Diarylpyrazole and vanillin hybrids: Synthesis, biological activity and DFT studies

  摘要：

  Herein, we report the design and synthesis of 13 diarylpyrazole hybrids with vanillin constructed as dual compounds against oxidative stress and diabetes. Compounds were tested in two different antioxidant assays. It was found that all compounds showed an important antioxidant activity in both DPPH and ORAC models and the activity was even more remarkable than vanillin. In addition, the hypoglycemic effect of compounds 1, 2, 4 and 12 was evaluated. Interestingly, compound 1 had the most potent hypoglycemic effect with a glycemia reduction of 71%, which was higher than rimonabant. Finally, a DFT study to propose a reasonable antioxidant mechanism is detailed. Both thermodynamic and kinetic studies indicated that the most feasible mechanism consists in the HAT abstraction of the phenolic hydrogen due to the formation of an stable transition state through the most rapid and exergonic path, while the SPLET mechanism is the most significant at higher pH values. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.010
• 作为产物：
  描述：

  草酸二乙酯 在 lithium hexamethyldisilazane 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 0.75h， 以57%的产率得到ethyl 3-methyl-2,4-dioxo-4-phenylbutanoate lithium salt
  参考文献：
  名称：

  WO2007/148061

  摘要：

  公开号：

文献信息

• An Efficient One-pot Synthesis of Aryl-substituted 1-(Thiazol-2-yl)-1<i>H</i>-pyrazole-3-carboxylates via a Hantzsch Synthesis-Knorr Reaction Sequence
  作者：Chunhui Gu、Jiaojiao Zhai、Jianan Jiang、Hongwei Liu、Lei Wang、Dunru Zhu、Yafei Ji

  DOI：10.1002/cjoc.201300878

  日期：2014.2

  carbothioamide afforded 4‐aryl‐2‐(2‐(propan‐2‐ylidene)hydrazinyl)thiazoles via a Hantzsch‐thiazole synthesis, which reacted with 4‐aryl‐2,4‐diketoesters via a sequential Knorr‐pyrazole reaction to deliver a variety of aryl‐substituted ethyl 1‐(thiazol‐2‐yl)‐1H‐pyrazole‐3‐carboxylates in a one‐pot fashion with moderate to high yields. The key intermediates 4‐aryl‐2,4‐diketoesters, existing as its enolic lithium

  通过Hantzsch-噻唑合成反应处理α-溴代烷基芳基酮和2-（丙烷-2-亚烷基）肼碳硫代酰胺得到4-芳基-2-（2-（丙烷-2-亚烷基）肼基）噻唑通过顺序的克诺尔-吡唑反应以单锅方式以适度的温和性输送各种芳基取代的1-（噻唑-2-基）-1H-吡唑-3-羧酸酯的4-芳基-2,4-二酮酸酯高产。现有的关键中间体4-芳基-2,4-二酮酸酯是烯醇式锂盐，是通过烷基苯酮和草酸二乙酯的高产率叔丁基醇介导的克莱森缩合反应原位合成的。这类优雅的分子在两个不同的杂环核上均包含芳基，并且两个代表性分子的构型是通过单晶X射线晶体学确定的。
• PYRAZOLE DERIVATIVE
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP1591443B1

  公开（公告）日：2010-08-25
• Discovery of Rimonabant and its potential analogues as anti-TB drug candidates
  作者：J. M. Gajbhiye、N. A. More、Manoj D. Patil、R. Ummanni、S. S. Kotapalli、P. Yogeeswari、D. Sriram、V. H. Masand

  DOI：10.1007/s00044-015-1346-4

  日期：2015.7

  Rimonabant and its analogues have been synthesized in moderate to good yields using a simple synthetic route. All the newly synthesized compounds were subjected to in vitro screening against M. tuberculosis and M. smegmatis. The most potent analogue JMG-14 exhibits MIC value of 3.13 compared to 3.25 and 50 A mu g/ml for ethambutol and pyrazinamide, respectively. The molecular docking reveals that pyrazole ring, number and position of halogen atoms play a crucial role in deciding interactions with MTCYP-121. These findings open up a new avenue in the search of potent anti-TB drugs with rimonabant and its novel analogue JMG-14 as lead molecules.
• PYRAZOLE DERIVATIVES AS CANNABINOID RECEPTOR ANTAGONISTS
  申请人：The University of Connecticut

  公开号：EP1224173B1

  公开（公告）日：2005-10-12
• WO2007/148062
  申请人：——

  公开号：——

  公开（公告）日：——