N-alpha-benzoyl-phenylglycine | 119656-49-4

• 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-alpha-benzoyl-phenylglycine
• 英文别名: N-Benzoyl-N-phenylglycine；benzoyl phenylglycine；N-benzoyl-N-phenyl-glycine；N-Benzoyl-N-phenyl-glycin；N-Phenyl-hippursaeure；Nα-benzoyl-phenylglycine；2-(N,1-diphenylformamido)acetic acid；2-(N-benzoylanilino)acetic acid
• CAS: 119656-49-4
• 化学式: C₁₅H₁₃NO₃
• mdl: MFCD01861478
• 分子量: 255.273
• InChiKey: NHWGJPPIJZCZBZ-UHFFFAOYSA-N

物化性质

• 熔点：
  187 °C
• 沸点：
  458.6±37.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-alpha-benzoyl-phenylglycine 在 吡啶 、 ammonium acetate 、 三氯氧磷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 4-trifluoromethyl-1,2-diphenylimidazole
  参考文献：
  名称：

  Convenient Synthesis of 4-Trifluoromethyl-Substituted Imidazole Derivatives.

  摘要：

  美索离子4-三氟乙酰基-1,3-噁唑啉-5-醇盐（1）是由N-酰基-N-烷基甘氨酸（2）与三氟乙酸酐反应得到的，能够与氨反应生成4-三氟甲基-3,4-二氢咪唑（3），产率高。3的脱水反应高产率地生成4-三氟甲基咪唑（4）。1到3的这一新颖环转换过程是通过氨对环C-2位点的区域选择性攻击实现的。

  DOI：

  10.1248/cpb.49.461
• 作为产物：
  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

文献信息

• Cyclisation of α-acylamino-acids in the presence of perchloric acid to give 5-oxo-Δ²-oxazolinium perchlorates
  作者：G. V. Boyd、P. H. Wright

  DOI：10.1039/p19720000909

  日期：——

  benzaldehyde to give the hydroperchlorate of the labile geometrical isomer of 4-benzylidene-2-phenyloxazolinone. Ten N-substituted oxo-oxazolinium perchlorates were prepared and their reactions with benzaldehyde and amines are reported. The bicyclic perchlorate, obtained from p-nitrobenzoyl-L-proline, is easily racemised, probably via a mesoionic oxazolium oxide; the corresponding diphenylamino-compound is optically

  乙酸酐和高氯酸的简单α酰氨基酸的产率-5-氧代Δ动作2个-oxazolinium高氯酸盐，其可以被去质子化，以相应的饱和恶唑啉-5-酮。N-苯甲酰基-L-苯基丙氨酸得到L -4-苄基-2-苯基恶唑啉酮的氢高氯酸盐。由马尿酸制得的盐在用水，甲醇和各种胺处理后会发生开环反应。它与苯甲醛缩合，得到4-亚苄基-2-苯基恶唑啉酮的不稳定几何异构体的氢高氯酸盐。制备了十种N-取代的氧代-恶唑啉鎓高氯酸盐，并报道了它们与苯甲醛和胺的反应。从p获得的双环高氯酸盐-硝基苯甲酰基-L-脯氨酸很容易消旋，可能是通过中性离子的恶唑鎓氧化物消旋；相应的二苯氨基化合物是光学稳定的。
• [EN] (S)-CSA SALT OF S-KETAMINE, (R)-CSA SALT OF S-KETAMINE AND PROCESSES FOR THE PREPARATION OF S-KETAMINE<br/>[FR] SEL (S)-CSA DE S-KÉTAMINE, SEL (R)-CSA DE S-KÉTAMINE ET PROCÉDÉS PERMETTANT LA PRÉPARATION DE S-KÉTAMINE
  申请人：CHEN CHENG YI

  公开号：WO2016180984A1

  公开（公告）日：2016-11-17

  The present invention is directed to processes for the preparation of esketamine. The present invention is further directed to processes for the resolution of S-ketamine from a racemic or enantiomerically enriched mixture of ketamine. The present invention is further directed to an (S)-CSA salt of S-ketamine, more particularly a monohydrate form of the (S)-CSA salt of S-ketamine; and to an (R)-CSA salt of R-ketamine.

  本发明涉及制备左旋氯胺酮的方法。本发明进一步涉及从消旋或对映体富集混合物中分离S-氯胺酮的方法。本发明还涉及S-氯胺酮的(S)-CSA盐，更具体地是(S)-CSA盐的单水合物形式；以及R-氯胺酮的(R)-CSA盐。
• Direct Amide Formation from <i>N</i>-Arylglycine Ethyl Esters and Carboxylic Acids Catalysed by Phenylboronic Acid
  作者：Wenhua Huang、Wen-Bin Sha

  DOI：10.3184/174751913x13729583884275

  日期：2013.8

  The phenylboronic acid-catalysed reaction of an N-arylglycine ethyl ester with various carboxylic acids, including N-acyl-N-phenylglycines, directly affords an amide or a dipeptide in 13–73% yields.

  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。
• Synthesis and Cycloaddition Reactions of Stabilized Münchnones
  作者：Taban K. K. Kakaawla、Will C. Hartley、Joseph P. A. Harrity

  DOI：10.1002/ejoc.201600486

  日期：2016.6

  A family of stabilized munchnones bearing an acyl group at C4 have been prepared and studied in alkyne cycloaddition reactions. These reactions are highly regioselective, and the method represents a rapid and straightforward route to densely substituted pyrroles. Finally, the C4-stabilizing units can be further manipulated to furnish carboxylic acid and amide groups, or removed altogether to provide

  已经制备并在炔环加成反应中研究了一系列在 C4 处带有酰基的稳定 munchnones。这些反应具有高度的区域选择性，该方法代表了一种快速而直接的制备高密度吡咯的途径。最后，可以进一步操纵 C4 稳定单元以提供羧酸和酰胺基团，或完全去除以提供未取代的吡咯。
• Convenient Synthesis of 5-Trifluoroacetylated Imidazoles by Ring Transformation of Mesoionic 1,3-Oxazolium-5-olates.
  作者：Masami KAWASE、Setsuo SAITO

  DOI：10.1248/cpb.48.410

  日期：——

  Mesoionic 4-trifluoroacetyl-1, 3-oxazolium-5-olates (1), obtained from the reaction of N-acyl-N-alkylglycines (2) with trifluoroacetic anhydride, react with amidines to give 5-trifluoroacetylimidazoles (3) in moderate yield. The novel ring trandformations of 1 into 3 occur via an initial attack of amidines on the C-2 position of the ring.

  中性离子型 4-三氟乙酰基-1, 3-噁唑鎓盐-5-醇盐（1），是通过N-氨酰-N-烷基甘氨酸（2）与三氟乙酸酐反应得到的，能够与胍类化合物反应，生成5-三氟乙酰基咪唑（3），产率适中。这一新颖的环转化反应是通过胍类对环的C-2位的初步攻击实现的。