3-(4-硝基苯胺基)-3-氧代丙酸乙酯 | 10390-08-6

• 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: 3-(4-硝基苯胺基)-3-氧代丙酸乙酯
• 英文名称: N-(4-nitrophenyl)malonamic acid ethyl ester
• 英文别名: ethyl 3-((4-nitrophenyl)amino)-3-oxopropanoate；4-Nitrophenylcarbamoylessigsaeureethylester；Ethyl-4-nitrophenylcarbamoylacetat；Malonsaeure-ethylester-(4-nitro-anilid)；N-(4-Nitro-phenyl)-malonamidsaeure-aethylester；Malonsaeure-(4-nitro-anilid)-aethylester；Malonsaeure-aethylester-(4-nitro-anilid)；ethyl 3-(p-nitroanilino)-3-oxopropanoate；ethyl 2-(4-nitrophenylcarbamoyl)acetate；Ethyl 3-(4-nitroanilino)-3-oxopropanoate
• CAS: 10390-08-6
• 化学式: C₁₁H₁₂N₂O₅
• 分子量: 252.227
• InChiKey: MWYYWXZHCBCYII-UHFFFAOYSA-N

物化性质

• 熔点：
  95 °C
• 沸点：
  471.4±30.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  3-(4-硝基苯胺基)-3-氧代丙酸乙酯 在 PPA 作用下， 反应 3.0h， 以36%的产率得到2,4-二羟基-6-硝基喹啉
  参考文献：
  名称：

  Syntheses and binding affinities of 6-nitroquipazine analogues for serotonin transporter. part 2: 4-Substituted 6-nitroquipazines

  摘要：

  Eleven 4-substituted derivatives of 6-nitroquipazine were synthesized and evaluated for their abilities to displace [H-3]citalopram binding to the rat cortical synaptic membranes. Among them, 4-chloro-6-nitroquipazine was shown to possess the highest binding affinity (K-i - 0.03 nM) which was approximately 6 times higher than that of 6-nitroquipazine (K-i = 0.17 nM) itself. In this paper, we describe the syntheses of 4-substituted 6-nitroquipazine derivatives, the results of corresponding biological evaluation and the SAR study. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00028-8
• 作为产物：
  描述：

  异氰酸对硝基苯 在 盐酸 作用下， 以 乙醇 、 苯 为溶剂， 生成 3-(4-硝基苯胺基)-3-氧代丙酸乙酯
  参考文献：
  名称：

  Effenberger,F. et al., Chemische Berichte, 1966, vol. 99, p. 3892 - 3902

  摘要：

  DOI：

文献信息

• Formylnitroenamines: useful building blocks for nitrated pyridones and aminopyridines with functional groups
  作者：Yumi Nakaike、Daisuke Hayashi、Nagatoshi Nishiwaki、Yoshito Tobe、Masahiro Ariga

  DOI：10.1039/b815306j

  日期：——

  therefore, serve as C3N1 building blocks having a nitro group to afford nitropyridones and aminonitropyridines with a functional group at the 3-position. Upon treatment with malonic acid derivatives or β-keto esters, nitropyridones were obtained, whereas reactions with functionalized acetonitriles afford aminonitropyridines, via a formal transfer of an alkyl group from the ring nitrogen to the imino group

  β-甲酰基-β-亚硝胺1同时具有亲电甲酰基和亲核氨基，因此，作为具有硝基的C 3 N 1结构单元，可以提供在3-位具有官能团的硝基吡啶酮和氨基硝基吡啶。经治疗丙二酸可以得到硝基吡啶酮衍生物或β-酮酯，而与官能化乙腈的反应则是通过烷基从环氮到亚氨基的正式转移而得到氨基硝基吡啶。这些程序提供了制备具有硝基的杂环的实用方法。
• Carbene Radicals in Cobalt(II)-Porphyrin-Catalysed Carbene Carbonylation Reactions; A Catalytic Approach to Ketenes
  作者：Nanda D. Paul、Andrei Chirila、Hongjian Lu、X. Peter Zhang、Bas de Bruin

  DOI：10.1002/chem.201301731

  日期：2013.9.23

  One‐pot radicals: Cobalt(III)–carbene radicals, generated by metallo‐radical activation of diazo compounds and N‐tosylhydrazone sodium salts with cobalt(II) complexes of porphyrins, readily undergo radical addition to carbon monoxide, allowing the catalytic production of ketenes. These ketenes subsequently react with various amines, alcohols and imines in one‐pot tandem transformations to produce differently

  一锅自由基：钴（III）-卡宾自由基，由重氮化合物和N-甲苯磺酰腙钠盐与卟啉的钴（II）络合物的金属自由基活化产生，容易与一氧化碳发生自由基加成，从而催化生产酮。这些乙烯酮随后与各种胺、醇和亚胺在一锅串联转化中反应，以良好的分离产率生产不同取代的酰胺、酯和 β-内酰胺。
• Tunable Copper-Catalyzed Reaction of C₆₀ with 2-Ethoxycarbonylacetamides and Subsequent BF₃·Et₂O-Mediated Isomerization of the Generated Dihydrofuran-Fused Fullerenes to Fulleropyrrolidinones
  作者：Qiaoqiao Teng、Yi-Chen Tan、Chun-Bao Miao、Xiao-Qiang Sun、Hai-Tao Yang

  DOI：10.1021/acs.joc.8b02547

  日期：2018.12.21

  copper-catalyzed reaction of C60 with 2-ethoxycarbonylacetamides using air as the oxidant has been explored, which selectively affords methanofullerenes (2) and dihydrofuran-fused fullerenes (3) under the CuI/DMAP and CuCl/NMI catalytic systems, respectively. Furthermore, the generated dihydrofuran-fused fullerenes could be transformed to fulleropyrrolidinones (4 and 5) upon treatment with BF3·Et2O.

  已经研究了使用空气作为氧化剂的C 60与2-乙氧基羰基乙酰胺的可调谐铜催化反应，该反应分别在CuI / DMAP和CuCl / NMI催化体系下分别提供了甲基富勒烯（2）和二氢呋喃稠合的富勒烯（3）。 。此外，在用BF 3 ·Et 2 O处理后，生成的二氢呋喃稠合的富勒烯可以转化为全吡咯烷酮（4和5）。
• Process for the production of malonic acid derivative compounds
  申请人：——

  公开号：US04736056A1

  公开（公告）日：1988-04-05

  This invention relates to a process for preparing a malonic acid derivative compound of formula (i) depicted herein in high yield and high purity by reacting a malonic acid derivative compound of formula (ii) depicted herein with an alkylating agent of formula (iii) depicted herein in the presence of a solvent and a base.

  这项发明涉及一种制备高产率和高纯度的分子式为(i)的丙二酸衍生物化合物的过程，通过将分子式为(ii)的丙二酸衍生物化合物与分子式为(iii)的烷基化剂在溶剂和碱的存在下反应。
• 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