ethyl 3-(isoquinolin-1-yl)-2-methyl-3-oxopropanoate | 1383532-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: ethyl 3-(isoquinolin-1-yl)-2-methyl-3-oxopropanoate
• 英文别名: Ethyl 3-isoquinolin-1-yl-2-methyl-3-oxopropanoate
• CAS: 1383532-75-9
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: VOAJPDKSDVEQBX-UHFFFAOYSA-N

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：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异喹啉-1-羧酸乙酯 、 丙酸乙酯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以89%的产率得到ethyl 3-(isoquinolin-1-yl)-2-methyl-3-oxopropanoate
  参考文献：
  名称：

  Simple, fast and efficient synthesis of β-keto esters from the esters of heteroaryl compounds, its antimicrobial study and cytotoxicity towards various cancer cell lines

  摘要：

  A series of beta-keto esters were synthesized from heteroaryl esters and ethyl acetate using LiHMDS as base at -50 to -30 degrees C. The increase in yields of cross condensed product were observed and the percentage of self condensed product was reduced drastically by applying the suitable base (LiHMDS), solvent and the minimum amount of ethyl acetate. All these beta-keto esters were characterized using H-1 NMR, C-13 NMR and mass spectral data. A plausible mechanism is also depicted to prove the formation of trans-esterified products. All the synthesized compounds were subjected to test for their cytotoxicity towards various cancer cell lines and also tested for their antimicrobial activity towards various bacterial and fungal strains and some of them were found to have promising activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.008

文献信息

• Simple, fast and efficient synthesis of β-keto esters from the esters of heteroaryl compounds, its antimicrobial study and cytotoxicity towards various cancer cell lines
  作者：R. Venkat Ragavan、V. Vijayakumar、K. Rajesh、B. Palakshi Reddy、S. Karthikeyan、N. Suchetha Kumari

  DOI：10.1016/j.bmcl.2012.04.008

  日期：2012.6

  A series of beta-keto esters were synthesized from heteroaryl esters and ethyl acetate using LiHMDS as base at -50 to -30 degrees C. The increase in yields of cross condensed product were observed and the percentage of self condensed product was reduced drastically by applying the suitable base (LiHMDS), solvent and the minimum amount of ethyl acetate. All these beta-keto esters were characterized using H-1 NMR, C-13 NMR and mass spectral data. A plausible mechanism is also depicted to prove the formation of trans-esterified products. All the synthesized compounds were subjected to test for their cytotoxicity towards various cancer cell lines and also tested for their antimicrobial activity towards various bacterial and fungal strains and some of them were found to have promising activity. (C) 2012 Elsevier Ltd. All rights reserved.