2-(2,3-二氯-4-甲酰基苯氧基)乙酸乙酯 | 16861-23-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(2,3-二氯-4-甲酰基苯氧基)乙酸乙酯
• 英文名称: ethyl <2,3-dichloro-4-formylphenoxy> acetate
• 英文别名: ethyl [2,3-dichloro-4-formylphenoxy]acetate；(2,3-Dichlor-4-formylphenoxy)essigsaeureethylester；Ethyl (2,3-dichloro-4-formylphenoxyacetate)；Ethyl-2.3-dichlor-4-formylphenoxyacetat；Ethyl (2,3-dichloro-4-formylphenoxy)acetate；ethyl 2-(2,3-dichloro-4-formylphenoxy)acetate
• CAS: 16861-23-7
• 化学式: C₁₁H₁₀Cl₂O₄
• 分子量: 277.104
• InChiKey: IWZPFUFJILGFLC-UHFFFAOYSA-N

物化性质

• 熔点：
  91-92 °C
• 沸点：
  379.9±37.0 °C(Predicted)
• 密度：
  1.371±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,3-二氯-4-甲酰基苯氧基)乙酸乙酯 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 生成 2-[2,3-dichloro-4-[(E)-2-nitroprop-1-enyl]phenoxy]acetic acid
  参考文献：
  名称：

  (Vinylaryloxy)acetic acids. A new class of diuretic agents. 3. [(2-Nitro-1-alkenyl)aryloxy]acetic acids

  摘要：

  A series of [(2-nitro-1-alkenyl)aryloxy]acetic acids was synthesized and tested in dogs for saluretic and diuretic activity. A number of these compounds exhibit a high order of activity on iv or po administration; representative of these is (E)-[2,3-dichloro-4-(2-nitropropenyl)phenoxy]acetic acid (5). The most highly active compounds are qualitatively similar in action to [2,3-dichloro-4-(2-methylenebutyryl)phenoxylacetic acid (ethacrynic acid) in causing a prompt increase in the excretion of water and of sodium and chloride ions in approximately equimolar amounts but are three to five times as potent. Potassium ion excretion is increased but less markedly than sodium excretion.

  DOI：

  10.1021/jm00228a009
• 作为产物：
  描述：

  2,3-二氯-4-羟基苯甲醛 、 溴乙酸乙酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以82%的产率得到2-(2,3-二氯-4-甲酰基苯氧基)乙酸乙酯
  参考文献：
  名称：

  芳氧基链烷酸作为血红蛋白变构特性的非共价改性剂

  摘要：

  立体特异性抑制镰状血红蛋白聚合物形成和/或变构增加 Hb 对氧的亲和力的血红蛋白 (Hb) 修饰剂已被证明可以预防镰状细胞病 (SCD) 的主要病理生理，特别是 Hb 聚合和红细胞镰状化。目前正在临床研究几种此类化合物用于治疗 SCD。基于先前报道的具有抗镰刀化特性的取代芳氧基链烷酸的非共价 Hb 结合特性，我们设计、合成和评估了 18 种新化合物（KAUS II 系列），以增强抗镰刀化活性。令人惊讶的是，选择的测试化合物没有表现出抗镰刀化作用或促进红细胞镰化。此外，这些化合物对 Hb 氧亲和力没有显着影响（或在某些情况下，甚至降低了对氧的亲和力）。与原型化合物 KAUS-23 复合的脱氧 Hb 的 X 射线结构显示，效应物结合在蛋白质的中央水腔中，为观察到的功能和生物活性提供了原子水平的解释。虽然结构修饰没有导致预期的生物学效应，但这些发现为设计候选抗镰刀菌剂提供了重要方向，并为新型 Hb

  DOI：

  10.3390/molecules21081057

文献信息

• [(Aminomethyl)aryloxy]acetic acid esters. A new class of high-ceiling diuretics. 3. Variation in the bridge between the aromatic rings to complete mapping of the receptor
  作者：Jacob J. Plattner、Yvonne C. Martin、Jill R. Smital、Cheuk Man Lee、Anthony K. L. Fung、Bruce W. Horrom、Steven R. Crowley、Andre G. Pernet、Paul R. Bunnell、Ki H. Kim

  DOI：10.1021/jm00379a016

  日期：1985.1

  Continued structural evaluation of the [(aminomethyl)aryloxy]acetic ester diuretics has produced a series of compounds in which the functional group that bridges the two aromatic rings has been varied. Diuretic screening of these analogues in rats indicates that the keto group can be effectively replaced with an ether or thio ether function with a slight increase in potency, whereas the methylene and sulfoxide linking groups lead to diminished saluretic potency. Replacement with either -SO2-, -COCO-, -CH2O-, -CONH- or direct bond results in a loss of activity. Although the series was designed according to QSAR criteria, the traditional linear free-energy properties of these compounds do not correlate with diuretic potency. However, conformational analysis of the series by potential energy calculations indicates that all active compounds have an accessible conformation that matches the bridge atom-carboxylate distance of the very potent dihydrobenzofuran analogue 56. Conformational calculations of several compounds in which the aminomethyl group was varied suggests that the active conformation is probably a low-energy conformation. Consideration of rotation about the bridge could not distinguish between two possible orientations of the aminomethyl ring in the active conformation. However, there is a quantitative negative linear correlation between diuretic potency and the protrusion into space of the group that bridges the two aromatic rings.
• (Vinylaryloxy)acetic acids. A new class of diuretic agents. 4. Various [(2-substituted and 2,2-disubstituted vinyl)aryloxy]acetic acids
  作者：Otto W. Woltersdorf、Charles M. Robb、John B. Bicking、L. Sherman Watson、Edward J. Cragoe

  DOI：10.1021/jm00229a024

  日期：1976.7

  A variety of [(2-substituted and 2,2-disubstituted vinyl)aryloxy]acetic acids was synthesized in which the substituents were primarily electron-withdrawing groups. These compounds were tested in dogs for their saluretic and diuretic properties. Many of the compounds exhibited significant activity; however, they were generally less potent than those reported in the three earlier papers in this series.
• PLATTNER, J. J.;MARTIN, Y. C.;SMITAL, J. R.;LEE, C. -M.;FUNG, A. K. L.;HO+, J. MED. CHEM., 1985, 28, N 1, 79-93
  作者：PLATTNER, J. J.、MARTIN, Y. C.、SMITAL, J. R.、LEE, C. -M.、FUNG, A. K. L.、HO+

  DOI：——

  日期：——
• BICKING J. B.; ROBB C. M.; WATSON L. S.; CRAGOE E. J., JR., J. MED. CHEM. <JMCM-AR>, 1976, 19 NO 4, 544-547
  作者：BICKING J. B.、 ROBB C. M.、 WATSON L. S.、 CRAGOE E. J., JR.

  DOI：——

  日期：——
• SCHULTZ E. M.; BICKING J. B.; DEANA A. A.; GOULD N. P.; STROBAUGH T. P.; +, J. MED. CHEM. <JMCM-AR>, 1976, 19, NO 6, 783-787
  作者：SCHULTZ E. M.、 BICKING J. B.、 DEANA A. A.、 GOULD N. P.、 STROBAUGH T. P.、 +

  DOI：——

  日期：——