ethyl 2-(3,5-dichloropyridin-2-yloxy)propionate | 79674-71-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: ethyl 2-(3,5-dichloropyridin-2-yloxy)propionate
• 英文别名: Ethyl 2-[(3,5-dichloropyridin-2-yl)oxy]propanoate；ethyl 2-(3,5-dichloropyridin-2-yl)oxypropanoate
• CAS: 79674-71-8
• 化学式: C₁₀H₁₁Cl₂NO₃
• 分子量: 264.108
• InChiKey: GXPKMIRCYPKALI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  48.42
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-(3,5-dichloropyridin-2-yloxy)propionate 在 水 、 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以10.1 g的产率得到2-(3,5-dichloropyridin-2-yloxy)propanoic acid
  参考文献：
  名称：

  Synthesis and structure–activity relationships of novel phenoxyacetamide inhibitors of the Pseudomonas aeruginosa type III secretion system (T3SS)

  摘要：

  The increasing prevalence of drug-resistant bacterial infections is driving the discovery and development not only of new antibiotics, but also of inhibitors of virulence factors that are crucial for in vivo pathogenicity. One such virulence factor is the type III secretion system (T3SS), which plays a critical role in the establishment and dissemination of Pseudomonas aeruginosa infections. We have recently described the discovery and characterization of a series of inhibitors of P. aeruginosa T3SS based on a phenoxyacetamide scaffold. To better characterize the factors involved in potent T3SS inhibition, we have conducted a systematic exploration of this structure, revealing several highly responsive structure-activity relationships indicative of interaction with a specific target. Most of the structural features contributing to potency were additive, and combination of those features produced optimized inhibitors with IC50 values <1 mu M. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.011
• 作为产物：
  描述：

  乳酸乙酯 、 3,5-二氯-2-氟吡啶 在 sodium 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 12.0h， 以52%的产率得到ethyl 2-(3,5-dichloropyridin-2-yloxy)propionate
  参考文献：
  名称：

  A comparison of N- versus O-alkylation of substituted 2-pyridones under Mitsunobu conditions

  摘要：

  2-Pyridones are well-known ambident nucleophiles which are capable of reacting with electrophiles through either the nitrogen or oxygen atom to form N-alkyl-2-pyridones or 2-alkoxypyridines, respectively. It has been shown that the ratio of these products can be affected by a number of factors including the nature of the electrophile, the base used for deprotonation, and the solvent. We have now discovered a relationship between the ratio of N- and O-alkylation products and the nature of substituents on the pyridone ring when the Mitsunobu reaction is used to alkylate 2-pyridones. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.054

文献信息

• HEILMANN, D.;KEMPTER, G., WISS. Z. PAD. HOCHSCH. K. LIEBKNECHT POTSDAM, 1981, 25, N 1, 35-38
  作者：HEILMANN, D.、KEMPTER, G.

  DOI：——

  日期：——