2-((3,5-dimethylphenyl)amino)-2-oxoacetic acid | 1018295-15-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-((3,5-dimethylphenyl)amino)-2-oxoacetic acid
• 英文别名: N-(3,5-dimethylphenyl)oxamic acid；[(3,5-Dimethylphenyl)amino](oxo)acetic acid；2-(3,5-dimethylanilino)-2-oxoacetic acid
• CAS: 1018295-15-2
• 化学式: C₁₀H₁₁NO₃
• mdl: MFCD10018452
• 分子量: 193.202
• InChiKey: YAYQBMCWKKCSDG-UHFFFAOYSA-N

物化性质

• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2-((3,5-dimethylphenyl)amino)-2-oxoacetic acid 在 lithium aluminium tetrahydride 、 potassium tert-butylate 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (S)-N1-(3,5-dimethylphenyl)-N2-(2-(2-(methoxymethyl)pyrrolidin-1-yl)phenyl)ethane-1,2-diamine
  参考文献：
  名称：

  Synthesis of amino acid derived imidazolidinium salts as new NHC precatalysts

  摘要：

  The preparation of new chiral symmetrically and unsymmetrically N,N'-disubstituted imidazolium based NHC salts Ib, IIb, IIIa-c and IVc-h from the amino acids L-proline and L-phenylalanine, is reported. Some preliminary tests have been carried out, demonstrating that the chiral NHCs give chiral induction in organometallic catalysis and can be used as organocatalysts. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.015
• 作为产物：
  描述：

  ethyl 2-[(3',5'-dimethylphenyl)amino]-2-oxoacetate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以855 mg的产率得到2-((3,5-dimethylphenyl)amino)-2-oxoacetic acid
  参考文献：
  名称：

  Synthesis of amino acid derived imidazolidinium salts as new NHC precatalysts

  摘要：

  The preparation of new chiral symmetrically and unsymmetrically N,N'-disubstituted imidazolium based NHC salts Ib, IIb, IIIa-c and IVc-h from the amino acids L-proline and L-phenylalanine, is reported. Some preliminary tests have been carried out, demonstrating that the chiral NHCs give chiral induction in organometallic catalysis and can be used as organocatalysts. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.015

文献信息

• Metal-free synthesis of carbamoylated dihydroquinolinones <i>via</i> cascade radical annulation of cinnamamides with oxamic acids
  作者：Pallav Suman、Kirti Tomar、Chandra Shekhar Nishad、Biplab Banerjee

  DOI：10.1039/d3ob01856c

  日期：——

  We report a metal-free procedure for the sustainable synthesis of carbamoylated dihydroquinolinones via tandem addition–cyclization of carbamoyl radicals to cinnamamides. Readily accessible, non-toxic and inexpensive oxamic acids are used as carbamoyl radical precursors. This highly straightforward method provides a mild and environmentally friendly route showing good atom economy and excellent functional

  我们报告了一种通过氨基甲酰基自由基串联加成环化成肉桂酰胺可持续合成氨基甲酰化二氢喹啉酮的无金属程序。易于获得、无毒且廉价的草酰胺酸被用作氨基甲酰基自由基前体。这种高度简单的方法提供了一种温和且环境友好的途径，具有良好的原子经济性和优异的官能团耐受性，可以一锅获得多种具有药用价值的重要氨基甲酰化二氢喹啉酮。级联环化也是模块化的、步骤经济的，具有广泛的底物范围，并且获得了良好至优异的产率的产物。此外，对空气和水的耐受性、操作简单性、低成本和可扩展性增强了所提出的合成策略的实用价值。初步机理研究表明，廉价且环保的过硫酸铵在级联过程中充当自由基引发剂，并由草酰胺酸生成氨基甲酰基自由基。该方法的合成效用通过药物分子的后期功能化得到了良好的产率进一步证明。
• Visible light mediated iron-catalyzed addition of oxamic acids to imines
  作者：Margaux Badufle、Frédéric Robert、Yannick Landais

  DOI：10.1039/d4ra02258k

  日期：2024.4.16

  be conducted using a 3-component strategy by simply mixing aldehydes, amines and oxamic acids in the presence of ferrocene, acting both as a photocatalyst under visible light and as a Lewis acid. The reaction proceeds through the addition onto the imine of a carbamoyl radical intermediate generated through a charge transfer from the carboxylate ligand to a Fe(III) species (LMCT).

  草酸可与亚胺加成，以通常良好的收率提供多种 α-氨基酸酰胺。该过程对于预形成的亚胺是有效的，但也可以使用三组分策略进行，通过在二茂铁存在下简单地混合醛、胺和草酰胺酸，既充当可见光下的光催化剂又充当路易斯酸。该反应通过将氨基甲酰自由基中间体加成到亚胺上来进行，该中间体是通过从羧酸配体到 Fe( III ) 物质 (LMCT) 的电荷转移而产生的。
• Synthesis of amino acid derived imidazolidinium salts as new NHC precatalysts
  作者：Ragnhild B. Strand、Trygve Helgerud、Tina Solvang、Christian A. Sperger、Anne Fiksdahl

  DOI：10.1016/j.tetasy.2011.11.015

  日期：2011.12

  The preparation of new chiral symmetrically and unsymmetrically N,N'-disubstituted imidazolium based NHC salts Ib, IIb, IIIa-c and IVc-h from the amino acids L-proline and L-phenylalanine, is reported. Some preliminary tests have been carried out, demonstrating that the chiral NHCs give chiral induction in organometallic catalysis and can be used as organocatalysts. (C) 2011 Elsevier Ltd. All rights reserved.