ethyl (E)-3-(2-chloro-5-methyl-3-pyridyl)-2-propenoate | 1256961-39-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-3-(2-chloro-5-methyl-3-pyridyl)-2-propenoate
• 英文别名: ethyl (E)-3-(2-chloro-5-methylpyridin-3-yl)prop-2-enoate
• CAS: 1256961-39-3
• 化学式: C₁₁H₁₂ClNO₂
• 分子量: 225.675
• InChiKey: FQHGUWKDIBPLQB-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氯-5-甲基吡啶-3-甲醛 、 三氟乙酰乙酸乙酯 在 哌啶 、 aluminum oxide 作用下， 反应 0.27h， 以90%的产率得到ethyl (E)-3-(2-chloro-5-methyl-3-pyridyl)-2-propenoate
  参考文献：
  名称：

  微波辅助的醛醇缩合消除α，β-不饱和酯和酮的便捷合成方法

  摘要：

  在哌啶存在下并在微波辐射下，将各种氟化的3-氧代酯/ 1,3-二酮与羰基化合物反应，得到高收率的（E）-α，β-不饱和酯和酮。系统研究表明反应是通过醛醇加合物的形成而进行的。该方法为C，C键的形成提供了一种新的简单方法。

  DOI：

  10.1002/hlca.201200526

文献信息

• Microwave-Assisted Convenient Synthesis of<i>α</i>,<i>β</i>-Unsaturated Esters and Ketones<i>via</i>Aldol-Adduct Elimination
  作者：Pathi Suman、Rayala Nageswara Rao、Bhimapaka China Raju

  DOI：10.1002/hlca.201200526

  日期：2013.8

  Various fluorinated 3‐oxo ester/1,3‐diketones were reacted with carbonyl compounds, in presence of piperidine and under microwave irradiation, to afford (E)‐α,β‐unsaturated esters and ketones in good yields. The systematic study reveals that the reaction proceeded through the formation of aldol adduct. The method provides a new and simple way for C,C bond formations.

  在哌啶存在下并在微波辐射下，将各种氟化的3-氧代酯/ 1,3-二酮与羰基化合物反应，得到高收率的（E）-α，β-不饱和酯和酮。系统研究表明反应是通过醛醇加合物的形成而进行的。该方法为C，C键的形成提供了一种新的简单方法。
• New and Facile Approach for the Synthesis of ( <i>E</i> )‐α,β‐Unsaturated Esters and Ketones
  作者：Bhimapaka China Raju、Pathi Suman

  DOI：10.1002/chem.201000883

  日期：2010.10.18

  A general and practical synthesis of (E)‐α,β‐unsaturated esters and ketones was achieved by the reaction of carbonyl compounds with ethyl‐4,4,4‐trifluoroacetoacetate and trifluoro‐substituted 1,3‐diketones in the presence of piperidine in dichloromethane at room temperature (≈40 °C) with excellent stereoselectivity (see scheme).

  在哌啶存在下，羰基化合物与4,4,4,4-三氟乙酰乙酸乙酯和三氟取代的1,3-二酮反应，可以实现（E）-α，β-不饱和酯和酮的一般和实用合成在室温（≈40°C）下于二氯甲烷中具有出色的立体选择性（参见方案）。
• Anti-mycobacterial, cytotoxic activities of Knoevenagel and (E)-α,β-unsaturated esters and ketones from 2-chloronicotinaldehydes
  作者：Pathi Suman、Rayala Nageswara Rao、Bhimapaka China Raju、Dharmarajan Sriram、Pulla Venkat Koushik

  DOI：10.1007/s00044-013-0622-4

  日期：2014.1

  Series of 2-chloronicotinaldehyde Knoevenagel derivatives 3a-r; (E)-alpha,beta-unsaturated esters and ketones 5a-k were prepared and evaluated for their in vitro anti-mycobacterial activity against Mycobacterium tuberculosis H(37)Rv (Mtb). Compounds 3e, 5b, 5d, 5e, 5g and 5i-k were shown potent to significant activity. Compound 5j is the most potent Mtb inhibitor (MIC: 4.89 mu M) when compared to standard drugs Ethambutol (MIC: 7.63 mu M) and Ciprofloxacin (MIC: 9.44 mu M). Eight compounds displayed potent/significant activity against M. tuberculosis were chosen for the cytotoxicity against three cell lines (Raw 264.7, MCF7, and HeLa). Compound 5j displayed low toxicity with high selective index (15-30) and is an interesting new compound may serve for the development of therapeutics targeted against anti-mycobacterial compounds. This is the first report assigning in vitro anti-mycobacterial inhibitory activity and structure-activity relationship for this class of substituted 2-chloronicotinaldehyde derivatives and presents new family of compounds.