3-(2,4-二氯-5-硝基苯基)-3-氧代丙酸乙酯 | 174312-93-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(2,4-二氯-5-硝基苯基)-3-氧代丙酸乙酯
• 英文名称: ethyl ester of (5-nitro-2,4-dichlorobenzoyl)acetic acid
• 英文别名: ethyl 3-(2,4-dichloro-5-nitrophenyl)-3-oxopropanoate；ethyl 2,4-dichloro-5-nitrobenzoylacetate；2,4-dichloro-5-nitrobenzoylacetic ester
• CAS: 174312-93-7
• 化学式: C₁₁H₉Cl₂NO₅
• mdl: MFCD00431317
• 分子量: 306.102
• InChiKey: UCLHXGMQGGFJNJ-UHFFFAOYSA-N

物化性质

• 熔点：
  141-143 °C
• 沸点：
  361.5±37.0 °C(Predicted)
• 密度：
  1.459±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2918300090

反应信息

• 作为反应物：
  描述：

  3-(2,4-二氯-5-硝基苯基)-3-氧代丙酸乙酯 在 盐酸 、 potassium tert-butylate 、 乙酸酐 、 tin(ll) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.83h， 生成 ethyl 7-chloro-1-cyclopropylamino-1,4-dihydro-6-formylamino-4-oxoquinoline-3-carboxylate
  参考文献：
  名称：

  Pyridonecarboxylic Acids as Antibacterial Agents. Part XVI. Imidazo- and Triazoloquinolones as Antibacterial Agents. Synthesis and Structure-Activity Relationships.

  摘要：

  合成了4, 5-二取代的6-环丙基-6, 9-二氢-9-氧代-1H-咪唑-(30-32)和三唑并[4, 5-f]喹啉-8-羧酸(33-35)从5, 6-二氨基喹诺酮25开始。咪唑并喹诺酮30-32的体外抗菌活性等于或优于相应的三唑并喹诺酮类似物33-35。至于C-5取代基，氟原子是H、F和Cl这三个基团中最有利的。在制备的化合物中，4-(环氨基)-5-氟-咪唑并喹诺酮31a-d对革兰氏阳性菌和革兰氏阴性菌均表现出有效且均衡的抗菌活性。还详细研究了 C-4 取代基（环状氨基）的结构-活性关系。

  DOI：

  10.1248/cpb.43.2123
• 作为产物：
  描述：

  2,4-dichloro-5-nitro benzoyl chloride 在 对甲苯磺酸 、 magnesium 作用下， 以 水 为溶剂， 反应 3.5h， 生成 3-(2,4-二氯-5-硝基苯基)-3-氧代丙酸乙酯
  参考文献：
  名称：

  Pyridonecarboxylic Acids as Antibacterial Agents. Part XVI. Imidazo- and Triazoloquinolones as Antibacterial Agents. Synthesis and Structure-Activity Relationships.

  摘要：

  合成了4, 5-二取代的6-环丙基-6, 9-二氢-9-氧代-1H-咪唑-(30-32)和三唑并[4, 5-f]喹啉-8-羧酸(33-35)从5, 6-二氨基喹诺酮25开始。咪唑并喹诺酮30-32的体外抗菌活性等于或优于相应的三唑并喹诺酮类似物33-35。至于C-5取代基，氟原子是H、F和Cl这三个基团中最有利的。在制备的化合物中，4-(环氨基)-5-氟-咪唑并喹诺酮31a-d对革兰氏阳性菌和革兰氏阴性菌均表现出有效且均衡的抗菌活性。还详细研究了 C-4 取代基（环状氨基）的结构-活性关系。

  DOI：

  10.1248/cpb.43.2123

文献信息

• Synthesis of pyrazolo[1,5-a]pyrimidines by the reaction of β-dicarbonyl compounds with 3,5-diamino-4-nitropyrazole
  作者：V. A. Makarov、V. A. Tafeenko、V. G. Granik

  DOI：10.1007/bf02317814

  日期：1998.12
• Synthesis and antimycobacterial activities of novel 6-nitroquinolone-3-carboxylic acids
  作者：Palaniappan Senthilkumar、Murugesan Dinakaran、Perumal Yogeeswari、Dharmarajan Sriram、Arnab China、Valakunja Nagaraja

  DOI：10.1016/j.ejmech.2008.02.031

  日期：2009.1

  Various 1-(substituted)-1,4-dihydro-6-nitro-4-oxo-7-(sub-secondary amino)-quinoline-3-carboxylic acids were synthesized from 2,4-dichlorobenzoic acid by six step synthesis. The compounds were evaluated for antimycobacterial in vitro and in vivo against Mycobacterium tuberculosis H37Rv (MTB), multi-drug resistant Mycobacterium tuberculosis (MDR-TB) and Mycobacterium smegmatis (MC2) and also tested for the ability to inhibit the supercoiling activity of DNA gyrase from M. smegmatis. Among the 48 synthesized compounds, 7-(4-((benzo[d][1,3]dioxol-5-yl)methyl)piperazin-1-yl)-1-cyclopropyl-1,4-dihydro-6-nitro-4-oxoquinotine-3-carboxylic acid (8c) was found to be the most active compound in vitro with MIC of 0.08 and 0.16 mu M against MTB and MDR-TB, respectively. In the in vivo animal model 8c decreased the bacterial load in lung and spleen tissues with 2.78 and 4.15-log 10 protections, respectively, at the dose of 50 mg/kg body weight. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Anti-coxsackievirus B3 activity of 2-amino-3-nitropyrazolo[1,5-a]pyrimidines and their analogs
  作者：Vadim A. Makarov、Olga B. Riabova、Vladimir G. Granik、Hans-Martin Dahse、Axel Stelzner、Peter Wutzler、Michaela Schmidtke

  DOI：10.1016/j.bmcl.2004.10.043

  日期：2005.1

  A novel class of 2-amino-4-nitropyrazolo[1,5-a]pyrimidines has been identified as potent inhibitors of coxsackievirus B3 replication. The synthesis of these compounds is based on the regioselective reaction of 3,5-diamino-5-nitropyrazole with unsymmetrical beta-diketones at catalysis by hydrochloric acid leading to 2-amino-4-nitropyrazolo[1,5-a]pyrimidines as key steps. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and amination of 1-alkyl-6-nitro-4-oxo-7-chloro-1,4-dihydroquinoline-3-carboxylic acids
  作者：R. G. Glushkov、N. B. Marchanko、I. B. Levshin、L. N. Dronova

  DOI：10.1007/bf02464110

  日期：1997.5
• Synthesis and antibacterial activity of 1,2-polymethylene-4-quinolone-3-carboxylic acids
  作者：R. G. Glushkov、N. B. Marchenko、A. N. Padeiskaya、L. D. Shipilova

  DOI：10.1007/bf00764991

  日期：1990.7