N,N-diethylmalonamic acid | 51149-20-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N,N-diethylmalonamic acid
• 英文别名: 3-(Diethylamino)-3-oxopropanoic acid
• CAS: 51149-20-3
• 化学式: C₇H₁₃NO₃
• 分子量: 159.185
• InChiKey: GDRRULULMXTYOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-diethylmalonamic acid 在 五氯化磷 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 N,N-diethyl-N'-(2-quinolinyl)malonamide
  参考文献：
  名称：

  1,2-Fused pyrimidines VII. 3-(Dialkylamino)-1H-pyrimido[1,2-a]quinolin-1-ones and 2-(dialkylamino)-4H-pyrimido[2,1-a]isoquinolin-4-ones as antiplatelet compounds

  摘要：

  A number of 3-(dialkylamino)-1H-pyrimido[1,2-a]quinolin-1 ones 3 and 2-(dialkylamino)-4H-pyrimido [2,1-a]isoquinolin-4-ones 4 were prepared by treating the corresponding chloro derivatives with an excess of dialkylamines. The highest in vitro antiplatelet activity was obtained when the dialkylamino substituent was 1-piperazinyl (compounds 3g and 4e). The novel 2-(1-piperazinyl)-4H-pyrido[ ,2-a]pyrimidin-4-one 2a was also prepared by an analogous procedure, which resulted in the most active compound towards all the platelet aggregation inducers used (ADP, collagen, A 23187). Moreover, some examples of 1-(dialkylamino)-3H pyrimido[l,2-a]quinolin-3-ones 5 and 4-(dialkylamino)-2H-pyrimido[2,1-a]isoquinolin-2-ones 6 were also obtained (together with negligible or lower amounts of the corresponding isomers 3 and 4, respectively) from the cyclocondensation of the appropriate ethyl N,N-dialkylmalonamate/phosphorus oxychloride reagents 13 with 2-aminoquinoline or 1-aminoisoquinoline. These;latter compounds showed a rather low antiplatelet activity.

  DOI：

  10.1016/0223-5234(96)88206-7
• 作为产物：
  描述：

  methyl 3-(N,N-diethylamino)-3-oxopropanoate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 以80%的产率得到N,N-diethylmalonamic acid
  参考文献：
  名称：

  醛与稳定的硫酰化物反应。2,3-环氧酰胺的高度立体选择性合成

  摘要：

  苯甲醛（1a），4-氯苯甲醛（1b）或3-硝基苯甲醛（1c）与N，N-二甲基-2-（二甲基磺酰亚氨基）乙酰胺（2）的反应仅产生反式-3-苯基-2,3-缩水甘油酰胺衍生物3a-c的收率很高。与2-硝基苯甲醛（1d）的相同反应，得到类似产物3d的15：1混合物（反式-顺式）。的反应2与2,3- ö异亚丙基d甘油醛（4中的（2S，3R，4R）的高度立体选择性合成）的结果-和（2R，3S，4R）-N，N-二甲基-2， 3-环氧-4,5-邻-异亚丙基-4，5-二羟基戊酰胺（5a）和（5b），（室温下86：14，-5至0℃下96：4，5a ：5b）。通过三种不同的方法进行构型分析：1）1 H-NMR偶合常数分析；2）与通过顺式或反式烯烃13和12的环氧化制备的顺式-反式类似物15a，b和7a，b的比较；和3）5a，7a和15a（或5b，7b和15b）的转换）异构体变成已知的（3S，4R）-3,4,5-三羟基戊酸1

  DOI：

  10.1016/s0040-4020(01)90089-4

文献信息

• A C=O⋅⋅⋅Isothiouronium Interaction Dictates Enantiodiscrimination in Acylative Kinetic Resolutions of Tertiary Heterocyclic Alcohols
  作者：Mark D. Greenhalgh、Samuel M. Smith、Daniel M. Walden、James E. Taylor、Zamira Brice、Emily R. T. Robinson、Charlene Fallan、David B. Cordes、Alexandra M. Z. Slawin、H. Camille Richardson、Markas A. Grove、Paul Ha‐Yeon Cheong、Andrew D. Smith

  DOI：10.1002/anie.201712456

  日期：2018.3.12

  C=O⋅⋅⋅isothiouronium interaction as key to efficient enantiodiscrimination in the kinetic resolution of tertiary heterocyclic alcohols bearing up to three potential recognition motifs at the stereogenic tertiary carbinol center. This discrimination was exploited in the isothiourea‐catalyzed acylative kinetic resolution of tertiary heterocyclic alcohols (38 examples, s factors up to >200). The reaction proceeds at low

  实验和计算研究的结合已经确定 C=O⋅⋅⋅isothiouronium 相互作用是在立体叔甲醇中心承载多达三个潜在识别基序的叔杂环醇的动力学分辨率中有效对映体区分的关键。这种区分在异硫脲催化的叔杂环醇的酰基化动力学拆分中得到了利用（38 个例子，s 因子高达 >200）。该反应在低催化剂负载量（通常为 1 mol%）下进行，异丁酸或乙酸酐作为酰化剂在温和条件下进行。
• Syntheses and antiinflammatory activity of malonamic acid, malonamate and malonamide derivatives of some heterocyclic compounds.
  作者：TOYOSHI KATAGI、MISAKO AOKI、MASAKO KASHIWAGI、KATSUYA OHATA、SHIGEKATSU KOHNO、TAMOTSU MURATA、TAKESHI INOI

  DOI：10.1248/cpb.33.4878

  日期：——

  Malonamate, malonic acid and malonamide derivatives of heterocyclic compounds were synthesized as part of a search for new biologically active compounds, e. g., those having antiinflammatory activity. Malonamates (1-17) were prepared by the reaction of amines containing heterocycles with malonic acid monoethyl ester. Hydrolysis of the malonamates gave the malonamic acids (18-24) in good yields. Malonamides (25-43) were synthesized by condensing amines with N-substituted malonamic acids. The antiinflammatory activity of these compounds was examined against carrageenin-induced rat paw edema. N-[2-(6-Methoxy) benzothiazolyl] malonamic acid (23) and its ethyl ester (7) showed significant activity.

  作为寻找新生物活性化合物（例如具有抗炎活性的化合物）的一部分，合成了异环化合物的丙二酸酯、丙二酸和丙二酰胺衍生物。通过将含异环的胺与丙二酸单乙酯反应制备了丙二酸酯（1-17）。丙二酸酯的水解得到丙二胺酸（18-24），产率良好。通过将胺与N取代的丙二胺酸缩合，合成了丙二胺（25-43）。这些化合物的抗炎活性在卡拉胶诱导的大鼠足部水肿中进行了测试。N-[2-(6-甲氧基)苯并噻唑基]丙二胺酸（23）及其乙基酯（7）显示出显著的活性。
• Hydrogen bonding-mediated foldamer-bridged zinc porphyrin-C60 dyads: ideal face-to-face orientation and tunable donor–acceptor interacion
  作者：Kui Wang、Yi-Shi Wu、Gui-Tao Wang、Ren-Xiao Wang、Xi-Kui Jiang、Hong-Bing Fu、Zhan-Ting Li

  DOI：10.1016/j.tet.2009.06.087

  日期：2009.9

  chloroform indicate that such a structural matching remarkably facilitates the intramolecular energy and electron transfer and charge separation between the two chromophores and also retards the recombination of the charge-separated state. Removing one hydrogen bond considerably reduces the energy and electron transfer. Further removing another one leads to no important interaction between the chromophores

  通过共价连接发色团在氢键芳基酰胺衍生的折叠架桥的相对端，已经合成了四个卟啉桥-C 60二联体。为了比较，还制备了相同构架的四种不含C 60的卟啉衍生物。完全氢键连接的桥使连接的卟啉和C 60部分以面对面的方式接触。1个在氯仿中的1 H NMR，UV-vis和荧光研究表明，这种结构匹配显着促进了两个发色团之间的分子内能量和电子转移以及电荷分离，并且还阻碍了电荷分离状态的重组。除去一个氢键会大大减少能量和电子转移。进一步除去另一种不会导致生色团之间发生重要的相互作用。
• Synthesis, in vitro antiplatelet activity and molecular modelling studies of 10-substituted 2-(1-piperazinyl)pyrimido[1,2- a ]benzimidazol-4(10 H )-ones
  作者：Mario Di Braccio、Giancarlo Grossi、Maria Grazia Signorello、Giuliana Leoncini、Elena Cichero、Paola Fossa、Silvana Alfei、Gianluca Damonte

  DOI：10.1016/j.ejmech.2013.01.026

  日期：2013.4

  The multistep preparation of the new 10-substituted 2-(1-piperazinyl)pyrimido[1,2-a]benzimidazol-4(10H)-ones 6a-o, and of the two isomers 10-ethyl-2-(diethylamino)pyrimido[1,2-a]benzimidazol-4(10H)-one 6p and 10-ethyl-4-(diethylamino)pyrimido[1,2-a]benzimidazol-2(10H)-one 13, as well as the in vitro evaluation of their inhibitory activity on human platelet aggregation induced in platelet-rich plasma by ADP, collagen or the Ca2+ ionophore A23187 were here described. Nine out of fifteen 2-(1-piperazinyl)derivatives (6g-o) showed good inhibitory properties towards all the platelet aggregation agonists used. Moreover, a molecular modelling study has been performed on two of the best compounds of this series (6i and 6o) to confirm in silico their interactions with the catalytic site of human platelet PDE3, using the X-ray data of the PDE3B isoform in complex with an inhibitor. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Foldamer-based pyridine–fullerene tweezer receptors for enhanced binding of zinc porphyrin
  作者：Zong-Quan Wu、Chang-Zhi Li、Dai-Jun Feng、Xi-Kui Jiang、Zhan-Ting Li

  DOI：10.1016/j.tet.2006.09.046

  日期：2006.11

  This paper reports the design and synthesis of a new series of hydrogen bonding-mediated foldamer-derived tweezer receptors that are used for efficient complexation of zinc porphyrin guest. One end of the rigidified aromatic amide backbone is incorporated with one fullerene unit, while another end is connected to one pyridine or imidazole unit. The H-1 NMR, UV-vis, and fluorescent investigations in chloroform revealed that, due to the intramolecular hydrogen bonding-driven preorganized folded conformation, the fullerene and pyridine units of the receptors are located with suitable spatial separation and consequently able to co-complex zinc porphyrin with remarkably increased stability. In contrast, the imidazole-incorporated receptor displays a weakened binding affinity possibly due to structural mismatching and large steric hindrance. The association constants of the complexes of the new receptors with zinc porphyrin have been determined. (c) 2006 Elsevier Ltd. All rights reserved.