2-(4-Nitrobenzoylamino)-2,3-dimethylbutanamide | 166538-35-8

• 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-(4-Nitrobenzoylamino)-2,3-dimethylbutanamide
• 英文别名: N-(1-amino-2,3-dimethyl-1-oxobutan-2-yl)-4-nitrobenzamide
• CAS: 166538-35-8
• 化学式: C₁₃H₁₇N₃O₄
• 分子量: 279.296
• InChiKey: DSNQKJVYEIFGLO-UHFFFAOYSA-N

物化性质

• 沸点：
  529.1±35.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-Nitrobenzoylamino)-2,3-dimethylbutanamide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以69%的产率得到5-Isopropyl-5-methyl-2-(4-nitro-phenyl)-1,5-dihydro-imidazol-4-one
  参考文献：
  名称：

  Preparation and NMR Spectra of Substituted 2-(4-Nitrophenyl)imidazolinones

  摘要：

  一系列11种取代的2-(4-硝基苯基)咪唑啉酮已经通过取代的2-(4-硝基苯甲酰氨基)烷酰胺的碱催化环化反应制备而成。在较高的甲氧基浓度下，环化反应可能伴随着硝基还原为偶氮基团。所有制备的物质均通过¹H和¹³C NMR谱鉴定。

  DOI：

  10.1135/cccc19960910
• 作为产物：
  描述：

  2-氨基-2,3-二甲基丁腈 在 硫酸 、 水 作用下， 以 氯仿 为溶剂， 生成 2-(4-Nitrobenzoylamino)-2,3-dimethylbutanamide
  参考文献：
  名称：

  Substituent Effect on Acidity of Substituted 2-(4-Nitrobenzoylamino)alkanamides in Methanol-Dimethyl Sulfoxide Mixtures

  摘要：

  已发送中文翻译结果。如果您有任何其他问题或需要进一步帮助，请随时告诉我。谢谢！

  DOI：

  10.1135/cccc19980085

文献信息

• Preparation, 1H and 13C NMR Spectra of Substituted 2-Benzoylaminocarboxamides
  作者：Miloš Sedlák、Aleš Halama、Jaromír Kaválek、Vladimír Macháček、Vojeslav Štěrba

  DOI：10.1135/cccc19950150

  日期：——

  A new type of herbicides based on imidazolinones has been introduced into agriculture under commercial names of Arsenal, Pursuit, Scepter, Assert etc. by American Cyanamid Company since 1983. These compounds destroy diocotyledonous weeds and are almost nontoxic for mammals and fish (LD₅₀ rat - 500 mg/kg, LD₅₀ trout - 300 mg/kg) and nonmutagenic according to the AMES test. The aim of the present work is to synthesize substituted 2-benzoylaminocarboxamides as starting materials for preparation of imidazolinones and potential biologically active substances (Formulae I - III).

  一种基于咪唑啉酮的新型除草剂自1983年起由美国赛诺美公司推出，商业名称为Arsenal、Pursuit、Scepter、Assert等。这些化合物能够消灭双子叶杂草，对哺乳动物和鱼类几乎无毒（LD₅₀ 大鼠 - 500 毫克/千克，LD₅₀ 鳟鱼 - 300 毫克/千克），根据AMES试验结果，这些化合物不具有致突变性。本研究的目的是合成取代的2-苯甲酰氨基羧酰胺，作为制备咪唑啉酮和潜在生物活性物质的起始原料（式 I - III）。
• Preparation and NMR Spectra of Substituted 2-(4-Nitrophenyl)imidazolinones
  作者：Miloš Sedlák、Aleš Halama、Jaromír Kaválek、Vladimír Macháček、Petr Mitaš、Vojeslav Štěrba

  DOI：10.1135/cccc19960910

  日期：——

  A series of 11 substituted 2-(4-nitrophenyl)imidazolinones have been prepared by base catalyzed cyclizations of substituted 2-(4-nitrobenzoylamino)alkanamides. At higher methoxide concentrations the cyclization can be accompanied by reduction of nitro group to azoxy group. All the substances prepared have been identified by ¹H and ¹³C NMR spectra.

  一系列11种取代的2-(4-硝基苯基)咪唑啉酮已经通过取代的2-(4-硝基苯甲酰氨基)烷酰胺的碱催化环化反应制备而成。在较高的甲氧基浓度下，环化反应可能伴随着硝基还原为偶氮基团。所有制备的物质均通过¹H和¹³C NMR谱鉴定。
• Preparation and NMR spectra of substituted 2-phenyl-5,5-dialkylimidazolinones
  作者：Miloš Sedlák、Aleš Halama、Petr Mitaš、Jaromír Kaválek、Vladimír Macháček

  DOI：10.1002/jhet.5570340421

  日期：1997.7

  Eighteen substituted 2-phenyl-5,5-dialkylimidazolinones 2 have been prepared by cyclizations of substituted 2-(N-benzoylamino)alkanamides 1. The cyclization of methylamides 1 proceeds at room temperature whereas primary amides are cyclized on boiling. The 1H and 13C nmr spectra of the imidazolinones are presented and the changes in their spectra connected with their protonation in hexadeuteriodimethyl

  通过取代的2-（N-苯甲酰基氨基）烷基酰胺1的环化反应已经制备了十八个取代的2-苯基-5，5-二烷基咪唑啉酮2。甲基酰胺1的环化反应在室温下进行，而伯酰胺在沸腾时被环化。给出了咪唑啉酮的1 H和13 C nmr光谱，并讨论了在六氘代二甲基亚砜-三氟乙酸混合物中其光谱与质子化有关的变化。
• Substituent Effect on Acidity of Substituted 2-(4-Nitrobenzoylamino)alkanamides in Methanol-Dimethyl Sulfoxide Mixtures
  作者：Petr Mitaš、Miloš Sedlák、Jaromír Kaválek

  DOI：10.1135/cccc19980085

  日期：——

  The dissociation constants of substituted 2-(4-nitrobenzoylamino)alkanamides, N-[2-(4-nitrobenzoylamino)alkanoyl]pyrrolidines, and N-alkyl-4-nitrobenzamides have been measured spectrophotometrically in 60 and 80% v/v DMSO. The pK_A values of these N-acids are discussed from the point of view of substituents at the acetamide α-carbon atom.

  已发送中文翻译结果。如果您有任何其他问题或需要进一步帮助，请随时告诉我。谢谢！
• Kinetics and Mechanism of Cyclization of Substituted 2-(Benzoylamino)alkanamides in Strongly Basic Medium
  作者：Miloš Sedlák、Jaromír Kaválek、Petr Mitaš、Vladimír Macháček

  DOI：10.1135/cccc19980394

  日期：——

  The cyclization reaction of substituted 2-(benzoylamino)alkanamides 1a-1i giving the corresponding substituted 2-phenylimidazol-4(5H)-ones 2a-2i has been studied. The equilibrium constants of reactions of compounds 1d-1f and 2-[(4-nitrobenzoyl)amino]-2,3-dimethylbutanenitrile (3) with methoxide have been determined in methanol-dimethyl sulfoxide media. For compound 1d and N-methyl derivatives 1a-1c, the cyclization rate constants have been measured in dependence on methoxide concentration in media of varying contents of dimethyl sulfoxide. The cyclization reaction mechanism involves formation of anion in a rapid pre-equilibrium and subsequent rate-limiting step: either formation of a cyclic intermediate or splitting off of OH^- ion from this intermediate. The product formed in the given medium is immediately transformed into its conjugate base. A change in reaction medium affects the reactions of all the compounds in the same way. The ratio of concentration of substrate to that of its anion at low methoxide concentrations is affected by the solvent composition (MeOH-DMSO). At higher methoxide and DMSO concentrations the reaction rate distinctly decreases, which can be interpreted by the transformation of reactive anion into non-reactive dianion. The corresponding N-methylbenzoylamino compounds are cyclized faster by a factor of 400 as compared with compounds having no methyl group at the benzamide group.

  研究了取代的2-(苯甲酰氨基)烷酰胺1a-1i的环化反应，得到相应的取代的2-苯基咪唑-4(5H)-酮2a-2i。在甲醇-二甲基亚砜介质中，确定了化合物1d-1f和2-[(4-硝基苯甲酰)氨基]-2,3-二甲基丁腈(3)与甲氧基的反应平衡常数。对于化合物1d和N-甲基衍生物1a-1c，测定了环化速率常数，取决于介质中甲氧基浓度的变化，介质中二甲基亚砜含量不同。环化反应机理涉及快速预平衡中阴离子的形成和随后的速率限制步骤：要么形成环中间体，要么从该中间体中分离出OH-离子。在给定介质中形成的产物立即转化为其共轭碱。反应介质的改变以相同的方式影响所有化合物的反应。在低甲氧基浓度下，底物浓度与其阴离子的比值受溶剂组成(MeOH-DMSO)的影响。在较高的甲氧基和DMSO浓度下，反应速率明显降低，这可以解释为反应性阴离子转化为非反应性二阴离子。与苯酰胺基上没有甲基的化合物相比，相应的N-甲基苯甲酰氨基化合物的环化速度快400倍。