N-（2,3-二甲基苯基）-3-氧代丁酰胺 | 55909-76-7

• 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: N-（2,3-二甲基苯基）-3-氧代丁酰胺
• 英文名称: N-(2,3-dimethylphenyl)-3-oxobutanamide
• CAS: 55909-76-7
• 化学式: C₁₂H₁₅NO₂
• mdl: MFCD00026247
• 分子量: 205.257
• InChiKey: JLBRPUWVDHSZKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-（2,3-二甲基苯基）-3-氧代丁酰胺 在 吡啶 作用下， 以 1,4-二氧六环 、 异丙醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and 3D-QSAR study of 1,4-dihydropyridine derivatives as MDR cancer reverters

  摘要：

  A series of symmetrical and unsymmetrical 1,4-dihydropyridines were synthesized by a rapid, single pot microwave irradiation (MWI) based protocol along with conventional approach and characterized by NMR, IR and mass spectroscopic techniques. The compounds were evaluated for their tumor cell cytotoxicity in HL-60 tumor cells. A 3D-QSAR study using CoMFA and CoMSIA was carried out to decipher the factors governing MDR reversing ability in cancer. The resulting contour maps derived by the best 3D-QSAR models provide a good insight into the molecular features relevant to the biological activity in this series of analogs. 3D contour maps as a result of 3D-QSAR were utilized to identify some novel features that can be incorporated into the 1,4-dihydropyridine framework to enhance the activity. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.011
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 2,3-二甲基苯胺 以91%的产率得到N-（2,3-二甲基苯基）-3-氧代丁酰胺
  参考文献：
  名称：

  Inter- and Intramolecular Cyclisation Reactions of Azoacetates Derived from Aryl Hydrazones of Ethylacetoacetate and Acetoacetanilides

  摘要：

  DOI：

  10.3987/com-08-11433

文献信息

• Structure–Activity Relationship Studies of Tetrahydroquinolone Free Fatty Acid Receptor 3 Modulators
  作者：Elisabeth Rexen Ulven、Tezz Quon、Eugenia Sergeev、Natasja Barki、Matjaz Brvar、Brian D. Hudson、Palash Dutta、Anders Højgaard Hansen、Line Ø. Bielefeldt、Andrew B. Tobin、Christine J. McKenzie、Graeme Milligan、Trond Ulven

  DOI：10.1021/acs.jmedchem.9b02036

  日期：2020.4.9

  activated by short-chain fatty acids, mediates health effects of the gut microbiota, and is a therapeutic target for metabolic and inflammatory diseases. The shortage of well-characterized tool compounds has however impeded progress. Herein, we report structure–activity relationship of an allosteric modulator series and characterization of physicochemical and pharmacokinetic properties of selected compounds

  游离脂肪酸受体 3（FFA3，以前称为 GPR41）由短链脂肪酸激活，介导肠道微生物群的健康影响，是代谢和炎症疾病的治疗靶点。然而，缺乏特征良好的工具化合物阻碍了进展。在此，我们报告了变构调节剂系列的结构-活性关系以及所选化合物的理化和药代动力学特性的表征，包括以前的和新的工具。两个代表，57 (TUG-1907) 和63 (TUG-2015)，显示出改善的溶解度和保留的效力。其中，57 种EC 50 = 145 nM，溶解度为 33 μM，在体内表现出高清除率，但在体外却是首选工具。相比之下，EC 50 = 162 nM 和溶解度为 9 μM 的63表现出较低的清除率，似乎更适合体内研究。使用57，我们首次证明FFA3激活导致小鼠背根神经节中的钙动员。
• Synthesis of Pyridin-2(1H)-one Derivatives: Temperature-Dependent Selectivity
  作者：Sandip Chikhalikar、Vijay Bhawe、Madhukar Jachak、Maruti Ghagare

  DOI：10.1002/ejoc.201100800

  日期：2011.10

  methods for the synthesis of biologically important pyridin-2(1H)-one derivatives have been developed. The behavior of enamine 1 with aromatic amines in an aqueous solution of HCl resulted in the formation of substituted enamines 2a–f at ambient temperature. The obtained product enamines 2a–f, upon treatment with 2,2,6-trimethyl-4H-1,3-dioxin-4-one, generated pyridin-2(1H)-one derivatives 5a–f along with

  已开发出两种合成具有生物学重要性的吡啶-2(1H)-one 衍生物的替代方法。烯胺 1 与芳香胺在 HCl 水溶液中的行为导致在环境温度下形成取代的烯胺 2a-f。获得的产物烯胺 2a-f，在用 2,2,6-trimethyl-4H-1,3-dioxin-4-one 处理后，生成了 pyridin-2(1H)-one 衍生物 5a-f 以及不需要的副产物8a-f。然而，从 β-烯胺酮 3a-f 开始，独家形成吡啶-2(1H)-one 衍生物 5a-f，这是在升高的温度下由烯胺 1 和芳香胺成功合成的。
• A Lewis acid-catalyzed tandem reaction enabling 2-arylglycerol derivative as versatile 1,3-biselectrophiles for the synthesis of 4H-chromenes and 2-pyridinones
  作者：Shaomin Chen、Tianjian Zhang、Zhenhua Xu、Bo You、Minghao Li、Yanlong Gu

  DOI：10.1016/j.cclet.2023.108130

  日期：2023.1

  Acid-catalyzed tandem reactions were established by employing a novel class of 2-arylglycerol derivative, 5-aryl-1,3-dioxan-5-ol, as versatile 1,3-biselectrophile. In the reactions, 5-aryl-1,3-dioxan-5-ol works like atropaldehydes or 2-aryl malondialdehydes, and can react with 2-naphthols and β-keto amides, allowing the synthesis of 4H-chromenes and 5-aryl-2-pyridinones. High yields, good functional

  通过使用一类新型 2-芳基甘油衍生物 5-芳基-1,3-二恶烷-5-醇（作为通用的 1,3-双亲电子试剂）建立了酸催化串联反应。在反应中，5-芳基-1,3-二恶烷-5-醇的作用类似于阿托醛或2-芳基丙二醛，并且可以与2-萘酚和β-酮酰胺反应，从而合成4 H-色烯和5-芳基-2-吡啶酮。高产率、良好的官能团耐受性、广泛的底物范围和简单的反应操作使该方案具有吸引力。
• Method of producing disazo pigment
  申请人：Toyo Ink Manufacturing Co. Ltd.

  公开号：EP1146088A1

  公开（公告）日：2001-10-17

  Method of producing a disazo pigment, in which a coupling reaction is carried out while feeding, into an acidic aqueous solution, a tetrazo aqueous solution containing a tetrazo component of benzidines and a coupler aqueous solution containing a coupling component, wherein the coupling component is a mixture comprising a main component represented by the formula (1): CH3COCH2CONH-X, wherein X represents a phenyl group optionally having one or the same or different plural substituents selected from the group consisting of a methyl group, methoxy group and chlorine atom; a first additional component represented by the formula (2): CH3COCH2CONH-Y, wherein Y represents a phenyl group having a substituent selected from the group consisting of -CONR2 group, -SO2NR2 group and -NHCOR group, and the phenyl group may further have a substituent selected from the group consisting of a methyl group, methoxy group, chlorine atom, -CONR2 group, -SO2NR2 group and -NHCOR group, and wherein Rs may be the same or different mutually, and represent a hydrogen atom, C1 to C4 alkyl group (the alkyl groups may be mutually connected to form a ring) or C1 to C4 alkylene NR'2, further wherein R's represent a hydrogen atom or C1 to C4 alkyl groups which may be mutually different (the alkyl groups may be mutually connected to form a ring); and, a second additional component represented by the formula (3): CH3COCH2CONH-Z, wherein Z represents a phenyl group substituted by any one of a carboxyl group or alkali metal salts thereof, hydroxyl group or sulfonic acid group or alkali metal salts thereof, and said phenyl group may further has a substituent selected from the group consisting of a methyl group, methoxy group, chlorine atom, carboxyl group or alkali metal salts thereof, hydroxyl group or sulfonic acid group or alkali metal salts thereof. According to the method, disazo pigments can be obtained which manifest excellent transparency and flowability of the inks produced therefrom, and excellent flushing property and flushing drain coloration resistance in the pigment production process, or excellent dispersibility when ink is formed under dry condition.

  生产二氮杂颜料的方法，其中在向酸性水溶液中加入含有苯并咪唑四氮杂组分的四氮杂水溶液和含有偶联组分的偶联剂水溶液的同时进行偶联反应，其中偶联组分是由式(1)代表的主组分组成的混合物：CH3COCH2CONH-X，其中 X 代表苯基，可选择具有一个或相同或不同的多个取代基，这些取代基可从甲基、甲氧基和氯原子组成的组中选择；由式（2）代表的第一附加组分：CH3COCH2CONH-Y，其中 Y 代表苯基，具有选自-CONR2 基团、-SO2NR2 基团和-NHCOR 基团组成的组的取代基，苯基可进一步具有选自甲基、甲氧基、氯原子、-CONR2 基团、-SO2NR2 基团和-NHCOR 基团组成的组的取代基、其中 Rs 可以相同或互不相同，并代表氢原子、C1 至 C4 烷基（烷基可以相互连接形成环）或 C1 至 C4 亚烷基 NR'2，R's 还代表氢原子或 C1 至 C4 烷基，它们可以互不相同（烷基可以相互连接形成环）；以及，由式 (3) 代表的第二种附加成分：CH3COCH2CONH-Z，其中Z代表被羧基或其碱金属盐、羟基或磺酸基或其碱金属盐中的任一种取代的苯基，所述苯基可进一步具有选自甲基、甲氧基、氯原子、羧基或其碱金属盐、羟基或磺酸基或其碱金属盐组成的组的取代基。根据该方法可获得二氮颜料，用其生产的油墨具有优异的透明度和流动性，在颜料生产过程中具有优异的冲洗性能和耐冲洗排水着色性能，或在干燥条件下形成油墨时具有优异的分散性。
• Synthesis, screening for antitubercular activity and 3D-QSAR studies of substituted N-phenyl-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxamides
  作者：Vijay Virsodia、Raghuvir R.S. Pissurlenkar、Dinesh Manvar、Chintan Dholakia、Priti Adlakha、Anamik Shah、Evans C. Coutinho

  DOI：10.1016/j.ejmech.2007.08.004

  日期：2008.10

  Multi-drug resistance to commonly used antitubercular drugs has propelled the development of new structural classes of antitubercular agents. This paper reports the synthesis, evaluation and 3D-QSAR analysis of a set of substituted N-phenyl-6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamides as antitubercular agents. Substituted acetoacetanilides were reacted with various aromatic aldehydes and urea which yielded the tetrahydropyrimidine derivatives with a phenyl carbamoyl group at C-5 position, and with various substitutions on the 4-phenyl and the N-phenyl aromatic rings. All compounds were screened for antitubercular activity against Mycobacterium tuberculosis H(37)Rv strain. The QSAR models were generated on a training set of 23 molecules. The molecules were aligned using the atom-fit and field-fit techniques. The CoMFA and CoMSIA models generated on the molecules aligned by the atom-fit method show a correlation coefficient (r(2)) of 0.98 and 0.95 with cross-validated r(2)(q(2)) of 0.68 and 0.58, respectively. The 3D-QSAR models were externally validated against a test set of 7 molecules for which the predictive r(2) (r(pred)(2)) is recorded as 0.41 and 0.32 for the CoMFA and CoMSIA models, respectively. The CoMFA and CoMSIA contours helped to design some new molecules with improved activity. (C) 2007 Elsevier Masson SAS. All rights reserved.