2-氨基-2-氧代-2-苯基苯甲酸乙酯 | 130627-10-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-氨基-2-氧代-2-苯基苯甲酸乙酯
• 英文名称: anthranilic acid phenacylester
• 英文别名: phenacyl anthranilate；Anthranilsaeurephenacylester；2-Oxo-2-phenylethyl 2-aminobenzoate；phenacyl 2-aminobenzoate
• CAS: 130627-10-0
• 化学式: C₁₅H₁₃NO₃
• mdl: MFCD00736387
• 分子量: 255.273
• InChiKey: RLYWUFWEFSCIKM-UHFFFAOYSA-N

物化性质

• 熔点：
  119-123°

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2-氨基-2-氧代-2-苯基苯甲酸乙酯 在 对甲苯磺酸 作用下， 以 N-甲基吡咯烷酮 、 乙酸乙酯 为溶剂， 反应 4.5h， 生成 2,5-二苯基吡嗪
  参考文献：
  名称：

  The Study of Cyclization of N-Acylphenacyl Anthranilates with Ammonium Salts under Various Conditions

  摘要：

  N-Acylphenacyl anthranilates were heated with ammonium salts in organic acid or NMP, and formation of various heterocyclic compounds was observed. Reaction results are strongly influenced by reaction conditions. The most interesting are imidazole derivatives with various anelated rings.

  DOI：

  10.3987/com-06-10899
• 作为产物：
  描述：

  2-nitro-benzoic acid phenacyl ester 在 氢气 、 铂 作用下， 以 乙醇 为溶剂， 以44%的产率得到2-氨基-2-氧代-2-苯基苯甲酸乙酯
  参考文献：
  名称：

  Sicker, Dieter, Journal fur praktische Chemie (Leipzig 1954), 1990, vol. 332, # 3, p. 336 - 344

  摘要：

  DOI：

文献信息

• Preparation of 1,2-disubstituted-3-hydroxy-4(1<i>H</i>)-quinolinones and the influence of substitution on the course of cyclization
  作者：Pavel Hradil、Jan Hlaváč、Karel Lemr

  DOI：10.1002/jhet.5570360121

  日期：1999.1

  Synthesis of 1,2-disubstituted-3-hydroxy-4(1H)-quinolinones by the cyclization of N-substituted phenacyl or acetonyl anthranilates is described. Two methods were employed for cyclization of anthranilates. Heating in polyphosphoric acid has a wide scope of applicability. The thermal cyclization in boiling N-methylpyrrolidone is limited by steric effect.

  描述了通过N-取代的苯甲酰基或乙酰基邻氨基苯甲酸酯的环化合成1，2-二取代的-3-羟基-4（1 H）-喹啉酮。两种方法被用于邻氨基苯甲酸酯的环化。在多磷酸中加热具有广泛的适用性。沸腾的N-甲基吡咯烷酮中的热环化受空间效应的限制。
• 2-Aryl-3-hydroxyquinolones, a new class of dyes with solvent dependent dual emission due to excited state intramolecular proton transfer
  作者：Dmytro A. Yushchenko、Volodymyr V. Shvadchak、Andrey S. Klymchenko、Guy Duportail、Yves Mély、Vasyl G. Pivovarenko

  DOI：10.1039/b601400c

  日期：——

  the fluorescence properties of a series of 2-aryl-3-hydroxyquinolones (3HQs) were investigated and compared with the properties of well-studied 3-hydroxyflavone. All these compounds were found to display dual fluorescence with well-separated bands in organic solvents and aqueous solutions. Using steady-state and time-resolved fluorescence spectroscopy, we showed that their dual fluorescence is due

  在此，研究了一系列2-芳基-3-羟基喹诺酮类（3HQs）的荧光性质，并将其与经过充分研究的性质进行了比较。 3-羟基黄酮。发现所有这些化合物在有机物中均显示带良好分隔带的双重荧光溶剂和水溶液。使用稳态和时间分辨荧光光谱，我们证明了它们的双重荧光是由于激发态的分子内质子转移反应。此外，发现大多数测试的3HQ的吸收光谱相似，表明它们对2-芳基环上的取代基不敏感。通过量子化学计算，这与这些分子的非平面性有关，这防止了两个芳族部分之间的共轭。唯一的例外是位置2处带有噻吩环的3HQ衍生物，由于其更平坦的结构，该光谱表现出红移光谱。与之形成鲜明对比的是，发射光谱，尤其是两个发射带的强度比在很大程度上取决于2-芳基环和杂环上的取代基氮。此外，N-甲基取代的3HQ（N–Me 3HQ）表现出很强的溶剂致变色特性，其荧光带强度比随其变化而变化很大。溶剂极性。此外，这些强度比的对数随与2-芳基环中取代基相关的哈
• Synthesis of 2-Aryl-3-hydroxyquinolin-4(1H)-ones
  作者：Pavel Hradil、Josef Jirman

  DOI：10.1135/cccc19951357

  日期：——

  Eight substituted phenacyl anthranilates have been prepared by reaction of sodium anthranilate with substituted phenacyl halides in dimethylformamide in the yields from 31 to 93%. The phenacyl esters were cyclized in polyphosphoric acid or by mere heating to give the respective substituted 2-aryl-3-hydroxyquinolin-4(1H)-ones in the yields from 77 to 98%. All the compounds prepared have been characterized by their ¹H and ¹³C NMR spectra.

  已经制备了八种取代苯乙酰基蒽酸盐，通过在二甲基甲酰胺中将苯乙酰卤代物与蒽酸钠反应而得，收率在31%至93%之间。这些苯乙酰基酯在聚磷酸或仅通过加热的条件下环化，得到相应的取代2-芳基-3-羟基喹啉-4(1H)-酮，收率在77%至98%之间。所有制备的化合物均通过它们的1H和13C核磁共振谱进行表征。
• Synthetic routes to 1,5-dihydro-5-oxo-4,1-benzoxazepines and to 5-oxooxazolo[3,2-a]quinolines
  作者：Sham S. Gandhi、Karen L. Bell、Martin S. Gibson

  DOI：10.1016/0040-4020(95)00880-h

  日期：1995.11

  The literature concerning phenacyl anthranilate, N- phenacylanthranilic acid and phenacyl N-phenacylanthranilate is clarified. Phenacyl anthranilate is dehydrated to 1,5-dihydro-5-oxo-2-pheny 1-4,1-benzoxazepine by treatment with phosphoryl chloride; other examples of this reaction are described. A preparation of 4-methyl-5-oxo-2-phenyloxazolo[3,2-a]quinoline from N-phenacylanthranilic acid and propionic

  的有关文献苯甲酰甲基邻氨基苯甲酸，ñ - phenacylanthranilic酸和苯甲酰甲基Ñ -phenacylanthranilate被澄清。通过用磷酰氯处理将邻氨基苯甲酸苯酯脱水为1，5-二氢-5-氧代-2-苯基1-4，1-苯并x并；描述了该反应的其他实例。报道了由N-苯并邻氨基邻氨基苯甲酸和丙酸酐制备4-甲基-5-氧代-2-苯基氧杂并[3，2-a]喹啉的方法。
• Synthesis of<i>N</i>-amino-3-hydroxy-2-phenyl-4(1<i>H</i>)-quinolinone
  作者：Lucie Spáčilová、Jan Hlaváč、Pavel Hradil、Iveta Fryšová、Miroslav Soural、Petr Krejčí、Michal Maloň

  DOI：10.1002/jhet.5570430437

  日期：2006.7

  phenacylester 1, were unsuccesfully tried as starting materials for the synthesis of N-amino-3-hydroxy-2-phenyl-4(1H)-quinolinone 8. The desired compound 8 was prepared by cyclization of N-acetyl as well as N-benzoyl-hydrazinobenzoic acid phenacylester 6a or 6b in polyphosphoric acid to afford N-acylamino-3-hydroxy-2-phenyl-4(1H)-quinolinone 7a or 7b, respectively. Surprisingly, the acyl group was resistant

  由邻氨基苯甲酸苯甲酸酯1制备的2-[（二取代-亚甲基）-肼基]苯甲酸苯甲酸酯2a-2d未成功尝试作为合成N-氨基-3-羟基-2-苯基-4（1）的原料H）-喹啉酮8。通过将N-乙酰基以及N-苯甲酰基-肼基苯甲酸苯甲酸酯6a或6b在多磷酸中环化得到N-酰基氨基-3-羟基-2-苯基-4（1H）-喹啉酮7a来制备所需的化合物8。或7b， 分别。出人意料的是，该酰基对盐酸和氢氧化钠溶液均具有抗侵蚀性。可以通过将化合物7a或7b分别在50％硫酸中煮沸而除去，以提供目标化合物8。