N-(2-硝基苯甲酰基) 甘氨酸 | 10167-23-4

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 甘氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(2-硝基苯甲酰基) 甘氨酸
• 中文别名: N-(2-硝基苯甲酰基)甘氨酸；n-(2-硝基苯甲酰基)-甘氨酸
• 英文名称: N-(2-nitrobenzoyl)glycine
• 英文别名: N-(2-Nitro-benzoyl)-glycin；N(o-Nitrobenzoyl)glycin；2-nitro-hippuric acid；2-Nitro-benzaminoessigsaeure；2-Nitro-hippursaeure；2-(2-Nitrobenzamido)acetic acid；2-[(2-nitrobenzoyl)amino]acetic acid
• CAS: 10167-23-4
• 化学式: C₉H₈N₂O₅
• mdl: MFCD00454931
• 分子量: 224.173
• InChiKey: HUKQWHBZPIMEDH-UHFFFAOYSA-N

物化性质

• 熔点：
  190℃
• 沸点：
  504.2±35.0 °C(Predicted)
• 密度：
  1.467

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-(2-硝基苯甲酰基) 甘氨酸 在 溶剂黄146 、 锌 作用下， 生成 3,4-二氢-1H-苯并[e][1,4]二氮杂卓-2,5-二酮
  参考文献：
  名称：

  Abderhalden; Riesz, Fermentforschung, 1931, vol. 12, p. 180,208

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 2-(2-nitrobenzamido)acetate 在 水 、 sodium hydroxide 作用下， 以 2-甲基四氢呋喃 为溶剂， 反应 1.0h， 生成 N-(2-硝基苯甲酰基) 甘氨酸
  参考文献：
  名称：

  Substituents Effect on the Erlenmeyer−Plöchl Reaction: Understanding an Observed Process Reaction Time

  摘要：

  A systematic study on hippuric acid substituents was performed in order to better understand the influence of stereoelectronic factors on the Erlenmeyer reaction rate. In addition, two reaction systems were evaluated: Hunig's base solvent free conditions and catalytic sodium acetate in 2-methyl-THF. The effect on reaction rate of electron withdrawing and electron donating groups are reported. Specifically, the study led to the conclusion that stereoelectronic factors have significant influence in one of our key Erlenmeyer reaction by affecting its reaction rate.

  DOI：

  10.1021/op100032s

文献信息

• o-Nitrobenzoyl group as a new amino protecting group for peptide synthesis and the synthesis of some anthranilyl peptides
  作者：A.K. Koul、J.M. Bachhawat、B. Prashad、N.S. Ramegowda、A.K. Mathur、N.K. Mathur

  DOI：10.1016/0040-4020(73)85005-7

  日期：1973.1

  and the resulting product on hydrogenation gives peptides, containing the anthranilyl group as —NH2 end group. N (anthranilyl)amino acids or peptides can also be obtained by reaction of isatoic anhydride on amino acids or peptides. The anthranilyl end group is easily cleaved by metal (Cu+2) catalysed hydrolysis to give α-amino acid peptides and the insoluble copper(II) anthranilate.

  N（邻硝基苯甲酰基）氨基酸可以使用DCC与其他氨基酸偶联，并且氢化后得到的产物产生包含邻氨基苯甲酰基作为-NH 2端基的肽。N（邻苯二甲酰基）氨基酸或肽也可以通过等位酸酐在氨基酸或肽上的反应获得。邻氨基苯甲酸酯端基很容易被金属（Cu +2）催化的水解裂解，得到α-氨基酸肽和不溶的邻氨基苯甲酸铜（II）。
• Amino acids in the synthesis of heterocyclic systems. Synthesis of γ-(5-(1,2,4-Triazinylidene))-α,β-dehydro-α-amino acid derivatives and 6<i>H</i>-pyrido[1,2-<i>d</i>][1,2,4]triazin-6-ones
  作者：Branko Stanovnik、Miha Tišler、Anton Čopar

  DOI：10.1002/jhet.5570320208

  日期：1995.3

  with 5(4H)-oxazolones 4 in acetic anhydride to give acetylated products 5, while in toluene-acetic acid mixture nonacetylated products 9 are formed. Both types of products were isolated as (E,Z) mixtures. Compounds 5 and 9 rearrange into 6H-pyrido[1,2-d]-[1,2,4]triazin-6-ones 12 by heating in formic acid or in xylene, respectively. Compounds 5 are transformed in the presence of nucleophiles, such as

  5-（1,2,4-三嗪基）取代的烯胺3与5（4反应ħ）-oxazolones 4在乙酸酐，得到乙酰化产物5，而在甲苯-乙酸混合物非乙酰化产物9而形成。两种类型的产物均以（E，Z）混合物的形式分离出来。通过在甲酸或二甲苯中加热，化合物5和9分别重排成6 H-吡啶并[1,2- d ]-[1,2,4]三嗪-6-酮12。化合物5在亲核试剂（如醇钠或酰胺钠）存在下通过阴离子形式转化10转化为相应的存在于2-（Z），4-（Z）中的α-氨基-2-丁烯酸的γ-（5-（1,2,4-三叠氮基））取代的衍生物的酯13和酰胺14形式。
• Stereospecific synthesis of dl-cyclopenin and dl-cyclopenol
  作者：J.D. White、W.E. Haefliger、M.J. Dimsdale

  DOI：10.1016/0040-4020(70)85023-2

  日期：——

  A stereospecific synthesis of dl-cyclopenin (1) is described corroborating previous structural and stereochemical assignments. The hippuric acid 10 was converted to cis ester 11 which was reduced and cyclized separately to cis and trans 3-benzylidene-4-methyl-1-H-1,4-benzodiazepin-2,5-diones 12 and 14. In an alternative approach, hippuric acid 5 was converted via oxazolone 4 to trans ester 9. Epoxidation

  描述了立体定向合成的dl-环戊素（1），证实了先前的结构和立体化学分配。将马尿酸10转化为顺式酯11，将其还原并分别环化为顺式和反式3-亚苄基-4-甲基-1- H -1,4-苯并二氮杂-2,5-二酮12和14。在另一种方法中，马尿酸5通过恶唑酮4转化为反式酯9。14的环氧化得到1。该方案的扩展提供了经由10 → 19 → 23 → 23 → 26 → 2到dl-环戊醇（2）的合成途径。
• Method for Producing Acetamidopyrrolidine Derivatives and Intermediate Compounds Thereof
  申请人：Kawana Asahi

  公开号：US20070249847A1

  公开（公告）日：2007-10-25

  A production method of an acetamidopyrrolidine derivative or a salt thereof comprising the reaction steps represented by the following formula: wherein R 1 represents a hydrogen atom or a C 1 -C 6 alkyl group; R 13 , R 14 , R 15 and R 16 each represent independently a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl group, a C 1 -C 6 alkoxy group, a hydroxyl group, a C 1 -C 6 haloalkyl group or a C 1 -C 6 haloalkoxy group; and R 21 represents an ester-type protecting group.

  一种制备乙酰胺基吡咯烷衍生物或其盐的生产方法，包括以下式子所表示的反应步骤：其中，R1表示氢原子或C1-C6烷基；R13、R14、R15和R16各自独立地表示氢原子、卤素原子、C1-C6烷基、C1-C6甲氧基、羟基、C1-C6卤代烷基或C1-C6卤代甲氧基；R21表示酯型保护基。
• Synthesis and in vitro aldose reductase inhibitory activity of compounds containing an N-acylglycine moiety
  作者：Jack DeRuiter、Blake E. Swearingen、Vinay Wandrekar、Charles A. Mayfield

  DOI：10.1021/jm00125a017

  日期：1989.5

  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.