N-(2'-methoxyethyl)-4,5-dimethyl-2-nitroaniline | 176907-05-4

• 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: N-(2'-methoxyethyl)-4,5-dimethyl-2-nitroaniline
• 英文别名: N-(3′-oxabut-1′-yl)-4,5-dimethyl-2-nitroaniline；N-(3'-oxabut-1'-yl)-4,5-dimethyl-2-nitroaniline；N-(2-methoxyethyl)-4,5-dimethyl-2-nitroaniline
• CAS: 176907-05-4
• 化学式: C₁₁H₁₆N₂O₃
• 分子量: 224.26
• InChiKey: WZLFUKFKARYPOC-UHFFFAOYSA-N

物化性质

• 沸点：
  382.6±42.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  67.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2'-methoxyethyl)-4,5-dimethyl-2-nitroaniline 在 palladium on activated charcoal 氢气 、 硼酸 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 生成 10-(2'-methoxyethyl)-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione
  参考文献：
  名称：

  Carell, Thomas; Epple, Robert; Gramlich, Volker, Angewandte Chemie, 1996, vol. 108, # 6, p. 676 - 679

  摘要：

  DOI：
• 作为产物：
  描述：

  4，5-二甲-2-硝基苯胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 N-(2'-methoxyethyl)-4,5-dimethyl-2-nitroaniline
  参考文献：
  名称：

  Investigation of Flavin-Containing DNA-Repair Model Compounds

  摘要：

  Irradiation of DNA with UV-B light causes the formation of mutagenic DNA lesions such as cis-syn and trans-syn cyclobutane pyrimidine dimers. DNA photolyases are flavin-dependent repair enzymes which directly revert the mutagenic cis-syn pyrimidine dimers into the corresponding monomers by a light-facilitated repair reaction. To gain deeper insight into the repair process, we recently prepared flavin-containing model compounds which are able to mimic the repair reaction (Carell, T.; Epple, R.; Gramlich, V. Angew. Chem., Int. Ed. Engl. 1996, 35, 620-623). This publication now contains a detailed description of the synthesis of a series of related model compounds and a comprehensive investigation of their cleavage properties. The results obtained help to unravel the requirements necessary for an efficient, flavin-mediated cleavage of pyrimidine dimers and provide insight into the factors on which the enzymatic repair process depends. The investigation of the cleavage reaction with cis-syn, trans-syn, and hans-anti cyclobutane pyrimidine dimer model compounds reveal an enhanced vulnerability for the cis-syn isomer. The trans-syn dimer is 10 times more stable, These results are comparable to those observed in a recent study on the E. coli enzyme. The excellent solubility of some of the model compounds has allowed a medium-dependent investigation of the flavin-initiated cleavage reaction. increased cleavage efficiencies are observed in polar solvents such as water (phi = 0.06) and acetonitrile (phi = 0.05). The quantum yields decrease by a factor of 4 in solvents with very low polarity such as dioxane (phi = 0.01). These results are not in agreement with earlier solvent-dependent evaluations performed with non-flavin-containing model compounds (Hartzfeld, D. G.; Rose, S. D. J. Am. Chem. Soc. 1993, 115,850-854). The results, however, suggest that the unusually polar flavin-binding pocket, observed in the X-ray crystal structure of the E, coli. photolyase, might be required to increase the catalytic repair efficiency. Investigations of the cleavage reaction in the presence of acid and base in organic solvents emphasize the strict requirement for a deprotonated reduced riboflavin chromophore. The determined pH values for half-maximal (pH = 6.5) and maximal (7 less than or equal to pH less than or equal to 9) cleavage efficiencies are in agreement with the pK(a) value (pK(a) = 6.3) of the reduced riboflavin and reveal that physiological conditions are required to reach maximum catalytic cleavage efficiency.

  DOI：

  10.1021/ja964097u

文献信息

• Thiourea-Enhanced Flavin Photooxidation of Benzyl Alcohol
  作者：Jiří Svoboda、Harald Schmaderer、Burkhard König

  DOI：10.1002/chem.200701319

  日期：2008.2.18

  irradiation, flavin oxidises 4-methoxybenzyl alcohol to the corresponding aldehyde using aerial O(2) as the terminal oxidant. We have observed that this reaction is significantly accelerated by the presence of thiourea. A series of thiourea-functionalised flavins has been prepared from flavin isothiocyanates and their photocatalytic efficiencies have been monitored by NMR. The alcohol photooxidation proceeds

  照射后，黄素使用航空O（2）作为末端氧化剂将4-甲氧基苄醇氧化为相应的醛。我们已经观察到，硫脲的存在大大促进了该反应。从异硫氰酸黄素制备了一系列硫脲官能化的黄素，并通过NMR监测了它们的光催化效率。酒精的光氧化反应迅速，清洁地进行，高达580个的高周转率，超过了先前报道的性能。从光谱学，电化学和动力学研究中得出了硫脲使光-氧化还原反应加速30倍以上的可能的机械原理。因此，硫脲充当了被激发的黄素对4-甲氧基苄醇进行初始光氧化的电子转移介体。该机制与黄素酶中的电子中继机制相似，为此提出了半胱氨酸亚磺酸中间体。硫脲介导的黄素光氧化还原过程的观察对于基于自然界最佳的氧化还原发色团设计更复杂的光催化剂具有重要价值。
• USE OF 10H-BENZO[G]PTERIDINE-2,4-DIONE DERIVATIVES
  申请人：Maisch Tim

  公开号：US20140128403A1

  公开（公告）日：2014-05-08

  Use of 10H-benzo[g]pteridine-2,4-dione derivatives as photosensitizers in the inactivation of microorganisms.

  10H-苯并[g]喹啉-2,4-二酮衍生物在灭活微生物中的光敏剂应用。
• Use of 10H-benzo[g]pteridine-2,4-dione derivatives
  申请人：TriOptoTec GmbH

  公开号：US10227348B2

  公开（公告）日：2019-03-12

  Use of 10H-benzo[g]pteridine-2,4-dione derivatives as photosensitizers in the inactivation of microorganisms.

  将 10H 苯并[g]蝶啶-2,4-二酮衍生物用作灭活微生物的光敏剂。
• Carell, Thomas; Epple, Robert; Gramlich, Volker, Angewandte Chemie, 1996, vol. 108, # 6, p. 676 - 679
  作者：Carell, Thomas、Epple, Robert、Gramlich, Volker

  DOI：——

  日期：——
• VERWENDUNG VON 10H-BENZO[G]PTERIDIN-2,4-DION-DERIVATEN
  申请人：Trioptotec GmbH

  公开号：EP2723342B1

  公开（公告）日：2018-12-05