2-ethyl-N-(4-nitrophenyl)malonamic acid ethyl ester | 863723-19-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-ethyl-N-(4-nitrophenyl)malonamic acid ethyl ester
• 英文别名: ethyl 2-(4-nitrophenylcarbamoyl)butanoate；Ethyl 2-[(4-nitrophenyl)carbamoyl]butanoate
• CAS: 863723-19-7
• 化学式: C₁₃H₁₆N₂O₅
• 分子量: 280.28
• InChiKey: SUXNDYFMBLTURP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-ethyl-N-(4-nitrophenyl)malonamic acid ethyl ester 在 PPA 、 三溴氧磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.5h， 生成 2,4-dibromo-3-ethyl-6-nitroquinoline
  参考文献：
  名称：

  Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 4: 3-Alkyl-4-halo-6-nitroquipazines

  摘要：

  On the basis of the structure activity relationship (SAR) of 4-chloro-6-nitroquipazine (K-i = 0.03 nM) and 3-fluoropropyl-6-nitroquipazine (K-i = 0.32 nM), 3-alkyl-4-halo-6-nitroquipazines were synthesized and tested for their potential abilities in vitro to displace [H-3]citalopram binding to the rat cortical membranes. Binding affinities of 3h and 4d were K-i = 2.70 +/- 0.32 and 2.23 +/- 0.46 nM. respectively. The syntheses of 3-alkyl-4-halo-6-nitroquipazine. their in vitro binding affinitics. and the SAR of C3, C4 position in 6-nitroquipazine are described. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.031
• 作为产物：
  描述：

  4-硝基苯胺 、 乙基丙二酸二乙酯 反应 18.0h， 以67%的产率得到2-ethyl-N-(4-nitrophenyl)malonamic acid ethyl ester
  参考文献：
  名称：

  Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. Part 4: 3-Alkyl-4-halo-6-nitroquipazines

  摘要：

  On the basis of the structure activity relationship (SAR) of 4-chloro-6-nitroquipazine (K-i = 0.03 nM) and 3-fluoropropyl-6-nitroquipazine (K-i = 0.32 nM), 3-alkyl-4-halo-6-nitroquipazines were synthesized and tested for their potential abilities in vitro to displace [H-3]citalopram binding to the rat cortical membranes. Binding affinities of 3h and 4d were K-i = 2.70 +/- 0.32 and 2.23 +/- 0.46 nM. respectively. The syntheses of 3-alkyl-4-halo-6-nitroquipazine. their in vitro binding affinitics. and the SAR of C3, C4 position in 6-nitroquipazine are described. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.031

文献信息

• Malonic Ester Amide Synthesis: An Efficient Methodology for Synthesis of Amides
  作者：Pankaj S. Mahajan、Jyoti P. Mahajan、Santosh B. Mhaske

  DOI：10.1080/00397911.2012.717671

  日期：2013.9.17

  “malonic ester amide synthesis” has been demonstrated, which uses α-substituted/unsubstituted diethyl malonates for the decarboxylative acylation of various aromatic/heteroaromatic primary/secondary amines to form one-carbon homologated amides, thus providing easy access to amides with odd/even chain lengths and an array of substituents on the alkyl/aryl part while avoiding use of acyl chlorides or peptide

  摘要 已经证明了“丙二酸酯酰胺合成”的通用方法，该方法使用 α-取代/未取代的丙二酸二乙酯对各种芳香族/杂芳香族伯胺/仲胺进行脱羧酰化，形成单碳同系酰胺，从而提供容易获得酰胺的方法。具有奇数/偶数链长和烷基/芳基部分上的一系列取代基，同时避免使用酰氯或肽偶联剂。补充材料可用于本文。转至出版商的 Synthetic Communications® 在线版以查看免费的补充文件。图形概要
• Synthesis of pyrrolidin-2-ones via tandem reactions of vinyl sulfonium salts under mild conditions
  作者：Chunsong Xie、Deyu Han、Yue Hu、Jinhua Liu、Tian Xie

  DOI：10.1016/j.tetlet.2010.07.108

  日期：2010.10

  A novel and efficient synthesis of pyrrolidin-2-ones through the tandem reactions of vinyl sulfonium salts with malonyl amides under very mild conditions is reported. The reaction demonstrates a wide tolerance toward various aryls, acyl, sulfonyl, and benzyl while aliphatic groups delivering the tetrahydro-2-oxofuran product.

  报道了在非常温和的条件下，通过乙烯基sulf盐与丙二酰胺的串联反应，新型高效合成吡咯烷二酮的方法。该反应表明对各种芳基，酰基，磺酰基和苄基具有宽的耐受性，而脂族基团递送四氢-2-氧呋喃产物。
• Synthesis of γ-lactams via a domino Michael addition/cyclization reaction of vinyl selenone with substituted amides
  作者：Silvia Sternativo、Benedetta Battistelli、Luana Bagnoli、Claudio Santi、Lorenzo Testaferri、Francesca Marini

  DOI：10.1016/j.tetlet.2013.10.004

  日期：2013.12

  A novel, simple, and flexible approach to α,α-disubstituted γ-lactams via a domino Michael addition/cyclization process involving the phenyl vinyl selenone and β-ketoamides, malonylamides, or β-cyanoamides is reported. The reactions proceed in good to excellent yields under mild reaction conditions.

  报道了一种新颖，简单且灵活的方法，该方法通过涉及苯基乙烯基硒酮和β-酮​​酰胺，丙二酰胺或β-氰基酰胺的多米诺骨牌迈克尔加成/环化过程制备α，α-二取代的γ-内酰胺。在温和的反应条件下，反应以良好的收率进行。