7-diethylamino-3-(4'-nitrophenyl)iminocoumarin | 41602-54-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 7-diethylamino-3-(4'-nitrophenyl)iminocoumarin
• 英文别名: N,N-diethyl-2-imino-3-(4-nitrophenyl)-2H-chromen-7-amine；2H-1-Benzopyran-7-amine, N,N-diethyl-2-imino-3-(4-nitrophenyl)-；N,N-diethyl-2-imino-3-(4-nitrophenyl)chromen-7-amine
• CAS: 41602-54-4
• 化学式: C₁₉H₁₉N₃O₃
• 分子量: 337.378
• InChiKey: XBKYDGMQFYFATR-UHFFFAOYSA-N

物化性质

• 沸点：
  504.0±60.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-diethylamino-3-(4'-nitrophenyl)iminocoumarin 在 盐酸 、 水 作用下， 以 乙醇 为溶剂， 以420 mg的产率得到3-(4-nitrophenyl)-7-(N,N-diethylamino)coumarin
  参考文献：
  名称：

  Selective Selenol Fluorescent Probes: Design, Synthesis, Structural Determinants, and Biological Applications

  摘要：

  Selenium (Se) is an essential micronutrient element, and the biological significance of Se is predominantly dependent on its incorporation as selenocysteine (Sec), the genetically encoded 21st amino acid in protein synthesis, into the active site of selenoproteins, which have broad functions, ranging from redox regulation and anti-inflammation to the production of active thyroid hormones. Compared to its counterpart Cys, there are only limited probes for selective recognition of Sec, and such selectivity is strictly restricted at low pH conditions. We reported herein the design, synthesis, and biological evaluations of a series of potential Sec probes based on the mechanism of nucleophilic aromatic substitution. After the initial screening, the structural determinants for selective recognition of Sec were recapitulated. The follow-up studies identified that probe 19 (Sel-green) responds to Sec and other selenols with more than 100-fold increase of emission in neutral aqueous solution (pH 7.4), while there is no significant interference from the biological thiols, amines, or alcohols. Sel-green was successfully applied to quantify the Sec content in the selenoenzyme thioredoxin reductase and image endogenous Sec in live HepG2 cells. With the aid of Sel-green, we further demonstrated that the cytotoxicity of different selenocompounds is correlated to their ability metabolizing to selenols in cells. To the best of our knowledge, Sel-green is the first selenol probe that works under physiological conditions. The elucidation of the structure-activity relationship for selective recognition of selenols paves the way for further design of novel probes to better understand the pivotal role of Sec as well as selenoproteins in vivo

  DOI：

  10.1021/ja5099676
• 作为产物：
  描述：

  4-(二乙氨基)水杨醛 、 对硝基苯乙腈 在 amberlite IRA-900 form OH 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以85%的产率得到7-diethylamino-3-(4'-nitrophenyl)iminocoumarin
  参考文献：
  名称：

  在有氧条件下铜催化亚氨基 C-N 键与芳基硼酸的形成

  摘要：

  开发了一种铜催化的、无配体和无碱的 C-N 交叉偶联反应，即在室温下，在无毒乙醇溶剂中，亚氨基色烯与芳基硼酸在空气中的反应。发现产品产率良好至中等。敏感亚胺官能团的保守性意味着该协议的温和性

  DOI：

  10.1055/s-0035-1561382

文献信息

• Polymer Supported Reagents: Novel Methodology for Selective and General Synthesis of Iminocoumarins
  作者：C. Mhiri、R. El Gharbi、Y. Le Bigot

  DOI：10.1080/00397919908085966

  日期：1999.10

  A selective synthesis of iminocoumarins 3 was accomplished, starting from salicylaldehydes 1 and nitriles 2, by the use of Amberlite IRA 900 resin as a polymeric solid support. The possibility of using various arylacetonitriles enhances the synthetic versatility of this strategy.
• Synthesis of New Iminocoumarins Bearing Parabanic Moieties
  作者：Leila Benmaktouf、Houcine Ammar、Yves Le Bigot、Souhir Abid

  DOI：10.1080/00397911003710562

  日期：2011.3.3

  [image omitted] The synthesis of novel substituted 3-p-nitro-phenyliminocoumarins and corresponding N-ureaiminocoumarins is described. The condensation of these materials with oxalyl chloride leads to the corresponding N-parabanic iminocoumarins, which have not previously been described, in moderate or good yields and high selectivity. The structures were characterized by Fourier transform infrared, 1H and 13C NMR, and elemental analysis.
• US4260776A
  申请人：——

  公开号：US4260776A

  公开（公告）日：1981-04-07
• Copper-Catalyzed Imino C–N Bond Formation with Aryl Boronic Acids under Aerobic Conditions
  作者：A. Kumar、Prashant Mandal

  DOI：10.1055/s-0035-1561382

  日期：——

  A copper-catalyzed, ligand- and base-free C–N cross-coupling reaction of iminochromenes with arylboronic acids in a nontoxic ethanol solvent at room temperature under air is developed. The product yields are found to be good to moderate. The conservation of the sensitive imine functional group implies the mildness of this protocol

  开发了一种铜催化的、无配体和无碱的 C-N 交叉偶联反应，即在室温下，在无毒乙醇溶剂中，亚氨基色烯与芳基硼酸在空气中的反应。发现产品产率良好至中等。敏感亚胺官能团的保守性意味着该协议的温和性
• Selective Selenol Fluorescent Probes: Design, Synthesis, Structural Determinants, and Biological Applications
  作者：Baoxin Zhang、Chunpo Ge、Juan Yao、Yaping Liu、Huichen Xie、Jianguo Fang

  DOI：10.1021/ja5099676

  日期：2015.1.21

  Selenium (Se) is an essential micronutrient element, and the biological significance of Se is predominantly dependent on its incorporation as selenocysteine (Sec), the genetically encoded 21st amino acid in protein synthesis, into the active site of selenoproteins, which have broad functions, ranging from redox regulation and anti-inflammation to the production of active thyroid hormones. Compared to its counterpart Cys, there are only limited probes for selective recognition of Sec, and such selectivity is strictly restricted at low pH conditions. We reported herein the design, synthesis, and biological evaluations of a series of potential Sec probes based on the mechanism of nucleophilic aromatic substitution. After the initial screening, the structural determinants for selective recognition of Sec were recapitulated. The follow-up studies identified that probe 19 (Sel-green) responds to Sec and other selenols with more than 100-fold increase of emission in neutral aqueous solution (pH 7.4), while there is no significant interference from the biological thiols, amines, or alcohols. Sel-green was successfully applied to quantify the Sec content in the selenoenzyme thioredoxin reductase and image endogenous Sec in live HepG2 cells. With the aid of Sel-green, we further demonstrated that the cytotoxicity of different selenocompounds is correlated to their ability metabolizing to selenols in cells. To the best of our knowledge, Sel-green is the first selenol probe that works under physiological conditions. The elucidation of the structure-activity relationship for selective recognition of selenols paves the way for further design of novel probes to better understand the pivotal role of Sec as well as selenoproteins in vivo