6-(4-tert-butylanilino)-3-[2-(trifluoromethyl)phenyl]-1H-pyrimidine-2,4-dione | 185435-31-8

• 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: 6-(4-tert-butylanilino)-3-[2-(trifluoromethyl)phenyl]-1H-pyrimidine-2,4-dione
• CAS: 185435-31-8
• 化学式: C₂₁H₂₀F₃N₃O₂
• 分子量: 403.404
• InChiKey: QSGFYPMONBBIGM-UHFFFAOYSA-N

物化性质

• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  66.89
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-(4-tert-butylanilino)-3-[2-(trifluoromethyl)phenyl]-1H-pyrimidine-2,4-dione 在 咪唑 、 sodium tetrahydroborate 、 硫酸 、 三氟化硼乙醚 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.25h， 生成 3-[2-[[Tert-butyl(dimethyl)silyl]oxymethyl]phenyl]-10-(4-tert-butylphenyl)pyrimido[4,5-b]quinoline-2,4-dione
  参考文献：
  名称：

  Atropisomeric Flavoenzyme Models with a Modified Pyrimidine Ring:  Syntheses, Physical Properties, and Stereochemistry in the Reactions with NAD(P)H Analogs

  摘要：

  Optically active 5-deazaflavin derivatives (3-aryl-10-(4-tert-butylphenyl)pyrimido[4,5-b]quinoline-2,4(3H,10H)-dione) with an axial chirality at the pyrimidine ring have been synthesized, and the kinetics of enantiomerization have been measured for some of them. The absolute configurations of these compounds have been determined by X-ray crystallographic analysis and chemical reactions for the first time in atropisomeric flavoenzyme models. Enantioface-differentiating (net) hydride-transfer reactions with 1-benzyl-1,4-dihydronicotinamide (BNAH) have revealed that the selectivity of the reacting face. of the 3-[2-(hydroxymethyl)phenyl] derivative 1 changes depending on the presence or absence of Mg2+; the hydroxymethyl group of 1 exerts steric inhibition in the absence of Mg2+, whereas it facilitates the approach of BNAH. in the presence of Mg2+ Asymmetric (net) hydride-transfer reactions with chiral 1,4-dihydro-2,4-dimethyl-N-(alpha-methylbenzyl)-1-propylnicotinamide (Me(2)PNPH) predict that the most favorable intermolecular arrangement of these two molecules at the transition state is the one in which the pyrimidine ring of 1 and the carbamoyl group of Me(2)PNPH tend to face each other and the maximum overlap of their molecular planes is achieved regardless of the presence or absence of Mg2+. The arrangement mimics that of FAD and NADPH in the active site of a flavoenzyme. The present result indicates an energetically favorable overlap of the molecular planes of a flavin and an NAD(P)H coenzyme, as well. as a significant influence of functional groups from an apoenzyme in proximity to a flavin coenzyme on the stereochemistry of biological redox reactions.

  DOI：

  10.1021/jo961799t
• 作为产物：
  描述：

  邻氨基三氟甲苯 在 sodium methylate 、 三氯氧磷 作用下， 以 甲醇 、 水 、 溶剂黄146 、 正丁醇 为溶剂， 反应 47.0h， 生成 6-(4-tert-butylanilino)-3-[2-(trifluoromethyl)phenyl]-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Atropisomeric Flavoenzyme Models with a Modified Pyrimidine Ring:  Syntheses, Physical Properties, and Stereochemistry in the Reactions with NAD(P)H Analogs

  摘要：

  Optically active 5-deazaflavin derivatives (3-aryl-10-(4-tert-butylphenyl)pyrimido[4,5-b]quinoline-2,4(3H,10H)-dione) with an axial chirality at the pyrimidine ring have been synthesized, and the kinetics of enantiomerization have been measured for some of them. The absolute configurations of these compounds have been determined by X-ray crystallographic analysis and chemical reactions for the first time in atropisomeric flavoenzyme models. Enantioface-differentiating (net) hydride-transfer reactions with 1-benzyl-1,4-dihydronicotinamide (BNAH) have revealed that the selectivity of the reacting face. of the 3-[2-(hydroxymethyl)phenyl] derivative 1 changes depending on the presence or absence of Mg2+; the hydroxymethyl group of 1 exerts steric inhibition in the absence of Mg2+, whereas it facilitates the approach of BNAH. in the presence of Mg2+ Asymmetric (net) hydride-transfer reactions with chiral 1,4-dihydro-2,4-dimethyl-N-(alpha-methylbenzyl)-1-propylnicotinamide (Me(2)PNPH) predict that the most favorable intermolecular arrangement of these two molecules at the transition state is the one in which the pyrimidine ring of 1 and the carbamoyl group of Me(2)PNPH tend to face each other and the maximum overlap of their molecular planes is achieved regardless of the presence or absence of Mg2+. The arrangement mimics that of FAD and NADPH in the active site of a flavoenzyme. The present result indicates an energetically favorable overlap of the molecular planes of a flavin and an NAD(P)H coenzyme, as well. as a significant influence of functional groups from an apoenzyme in proximity to a flavin coenzyme on the stereochemistry of biological redox reactions.

  DOI：

  10.1021/jo961799t