ethyl (N-benzoyl-N-phenylamino)acetate | 75277-57-5

• 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: ethyl (N-benzoyl-N-phenylamino)acetate
• 英文别名: ethyl 2-(N-phenylbenzamido)acetate；ethyl N-benzoyl-N-phenylglycinate；N-benzoyl-N-phenyl-glycine ethyl ester；N-Benzoyl-N-phenyl-glycin-aethylester；ethyl 2-(N-benzoylanilino)acetate
• CAS: 75277-57-5
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: REGFTBZETBZURW-UHFFFAOYSA-N

物化性质

• 沸点：
  423.4±37.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (N-benzoyl-N-phenylamino)acetate 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 N-alpha-benzoyl-phenylglycine
  参考文献：
  名称：

  Synthesis and in vitro aldose reductase inhibitory activity of compounds containing an N-acylglycine moiety

  摘要：

  A number of N-benzoylglycines (6), N-acetyl-N-phenylglycines (7), N-benzoyl-N-phenylglycines (8), and tricyclic N-acetic acids (9-12) were synthesized as analogues of the N-acylglycine-containing aldose reductase inhibitors alrestatin and 2-oxoquinoline-1-acetic acid. Derivatives of 6, which represent ring-simplified analogues of alrestatin, are very weak inhibitors of aldose reductase obtained from rat lens, producing 50% inhibition only at concentrations exceeding 100 microM. Compounds of series 7 were designed as ring-opened analogues of the 2-oxoquinolines. While these derivatives are more potent than compounds of series 6 (IC50S of 6-80 microM), they are less active than the corresponding 2-oxoquinolines. Analogues of series 8 were designed as hybrid structures of both alrestatin and the 2-oxoquinoline-1-acetic acids. These compounds are substantially more potent than compounds of series 6 and 7 and display inhibitory activities comparable to or greater than alrestatin or the 2-oxoquinolines (IC50S of 0.1-10 microM). Of the rigid analogues of 8, the most potent derivative is benzoxindole (12) with an IC50 of 0.67 microM, suggesting that fusion of the two aromatic rings of 8 in a coplanar conformation may optimize affinity for aldose reductase in this series.

  DOI：

  10.1021/jm00125a017
• 作为产物：
  描述：

  苯胺 在 potassium carbonate 、 苯硼酸 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 生成 ethyl (N-benzoyl-N-phenylamino)acetate
  参考文献：
  名称：

  苯基硼酸催化N-芳基甘氨酸乙酯和羧酸直接形成酰胺

  摘要：

  N-芳基甘氨酸乙酯与各种羧酸（包括 N-酰基-N-苯基甘氨酸）的苯基硼酸催化反应直接以 13-73% 的产率提供酰胺或二肽。

  DOI：

  10.3184/174751913x13729583884275

文献信息

• Effect of Substitution on the Intramolecular 1,3-Dipolar Cycloaddition of Alkene Tethered Münchnones
  作者：Guillaume Bélanger、Myriam April、Étienne Dauphin、Stéphanie Roy

  DOI：10.1021/jo061556t

  日期：2007.2.1

  dipolarophile and the münchnone on the intramolecular cycloaddition outcome was examined. It was found that either nonactivated or electron-poor alkenes can react with the münchnone if these alkenes are tethered at position 4 on the münchnone (2, R2 = alkene tether), whereas only an electron-poor alkene at position 2 (2, R3 = alkene tether) could undergo successful cycloaddition. Also, münchnones substituted

  N-酰基氨基酸的化学选择性活化，慕尼黑酮生成，分子内1,3-偶极环加成和开环的序列有效地产生了官能化的多环结构，例如环戊[ b ]吡咯或两性离子双环[4.3.0]壬烷或双环[3.3]。 [0]在一个操作中给出了辛烷值。这些两性离子物质是首次分离，然后还原为双环氨基醇。考察了双极亲和物和慕尼黑酮的取代对分子内环加成反应的影响。发现如果未活化的或贫电子的烯烃都可以在慕尼黑（4，R 2=烯烃系链），而只有位置2（2，R 3 =烯烃系链）的电子贫烯可成功进行环加成。同样，在位置2处被苯基（2，R 3 = Ph）取代的慕尼黑橡胶显示出显着的反应活性，而在位置4（2，R 2 = Ph）处的苯基具有非常有限的作用。
• Difluoroalkylation of Tertiary Amides and Lactams by an Iridium-Catalyzed Reductive Reformatsky Reaction
  作者：Phillip Biallas、Ken Yamazaki、Darren J. Dixon

  DOI：10.1021/acs.orglett.2c00438

  日期：2022.3.18

  An iridium-catalyzed, reductive alkylation of abundant tertiary lactams and amides using 1–2 mol % of Vaska’s complex (IrCl(CO)(PPh3)2), tetramethyldisiloxane (TMDS), and difluoro-Reformatsky reagents (BrZnCF2R) for the general synthesis of medicinally relevant α-difluoroalkylated tertiary amines is described. A broad scope (46 examples), including N-aryl- and N-heteroaryl-substituted lactams, demonstrated

  使用 1–2 mol % 的 Vaska 络合物 (IrCl(CO)(PPh 3 ) 2 )、四甲基二硅氧烷 (TMDS) 和二氟 Reformatsky 试剂 (BrZnCF 2 R) 对丰富的叔内酰胺和酰胺进行铱催化还原烷基化，用于描述了药用相关α-二氟烷基化叔胺的一般合成。范围广泛（46 个实例），包括N-芳基-和N-杂芳基取代的内酰胺，表现出优异的官能团耐受性。此外，后期药物功能化、克级合成和常见的下游转化证明了这种新方法的潜在合成相关性。
• Process to prepare taxol
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP1114815A2

  公开（公告）日：2001-07-11

  Novel compounds that can be used in a process to prepare taxol are of formulae II, III, IV and XI.         ϕ-CH(NHX3)-CH(OH)-CO-O-X1     (II)

  可用于制备紫杉醇工艺的新型化合物有式 II、III、IV 和 XI。 ϕ-CH(NHX3)-CH(OH)-CO-O-X1 (II)
• 574. Some new mesoionic compounds
  作者：Alexander Lawson、D. H. Miles

  DOI：10.1039/jr9590002865

  日期：——
• Oxazolidine ester
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP0912504B1

  公开（公告）日：2002-09-11