N-(4-甲氧基苯甲酰基)-N-甲基甘氨酸 | 133604-65-6

• 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-(4-甲氧基苯甲酰基)-N-甲基甘氨酸
• 英文名称: N-(4'-methoxybenzoyl)-N-methylglycine
• 英文别名: 2-[(4-Methoxybenzoyl)(methyl)amino]acetic acid；2-[(4-methoxybenzoyl)-methylamino]acetic acid
• CAS: 133604-65-6
• 化学式: C₁₁H₁₃NO₄
• mdl: MFCD09047586
• 分子量: 223.229
• InChiKey: GPUGAKRLKAOVTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2922509090

反应信息

• 作为反应物：
  描述：

  N-(4-甲氧基苯甲酰基)-N-甲基甘氨酸 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 4-Methoxy-N-methyl-N-[(E)-3,3,3-trifluoro-2-hydroxy-1-(2-hydroxy-phenylcarbamoyl)-propenyl]-benzamide
  参考文献：
  名称：

  Heterocyclization of 4-Trifluoroacetyl-1,3-oxazolium-5-olates with 1,4-Bis-nucleophiles

  摘要：

  Reactions of aromatic 1,4-bis-nucleophiles such as o-phenylenediamine and o-aminothiophenol, with mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1) gave regiospecifically seven member trifluoromethylated heterocycles such as 1,5-benzodiazepines (3) and 1,5-benzothiazepines (4). The reaction with o-aminophenol afforded non-cyclized products (5). The structures of 3, 4, and 5 were established by X-Ray diffraction analysis.

  DOI：

  10.3987/com-01-9325
• 作为产物：
  描述：

  肌氨酸 、 对甲氧基苯甲酰氯 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.5h， 以33%的产率得到N-(4-甲氧基苯甲酰基)-N-甲基甘氨酸
  参考文献：
  名称：

  Relative structure-inhibition analyses of the N-benzoyl and N-(phenylsulfonyl) amino acid aldose reductase inhibitors

  摘要：

  A number of N-benzoyl amino acids were synthesized and tested to compare structure-inhibition relationships with the isosteric N-(phenylsulfonyl) amino acid (PS-amino acid) aldose reductase inhibitors. Inhibition analyses with these series reveals that their kinetic mechanisms of inhibition are similar, but that significant differences in structure-inhibition relationships exist. For example, while the PS-alanines and PS-2-phenylglycines produce enantioselective inhibition (S > R), no consistent pattern of enantioselectivity is observed with the isosteric N-benzoylalanines and 2-phenylglycines. Also, N-methyl and N-phenyl substitution in the PS-amino acid series does not substantially alter inhibitory activity, while similar substitutions in the N-benzoyl series (particularly N-phenyl) results in a significant increase in inhibitory activity. Proton NMR analysis of the N-benzoylsarcosines reveals that these compounds exist as a mixture of rotamers in solutions including the enzyme assay buffer and that the preferred conformer is one in which the carboxymethyl moiety is trans to the aromatic ring. Similar analyses with the N-benzoyl-N-phenylglycines demonstrate that these derivatives exist exclusively in the trans rotameric conformation in solution. No such N-substituent effects on conformation were observed in the PS-amino acid series. These results suggest that the differences in structure-inhibition trends between these structurally related series may result from the effect of substituents on preferred conformation.

  DOI：

  10.1021/jm00111a030

文献信息

• Synthesis of Trifluoromethyl-Substituted Pyrazoles and 1,2,4-Triazines by Ring Transformation of Mesoionic 4-Trifluoroacetyl-1,3-oxazolium-5-olates with Phenylhydrazine
  作者：Masami Kawase、Hiromi Koiwai

  DOI：10.1248/cpb.56.433

  日期：——

  Mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates 1 were easily prepared by the cyclodehydration reaction of N-acyl-N-alkyl-alpha-amino acids with trifluoroacetic anhydride. Due to the presence of the trifluoromethyl ketone and the mesoionic five-membered oxazole, there are three reaction sites to be attacked by the nucleophiles at C-2, C-5 and the trifluoroacetyl group in 1. Based on this model,

  通过N-酰基-N-烷基-α-氨基酸与三氟乙酸酐的环脱水反应，可以容易地制备介电的4-三氟乙酰基-1,3-恶唑鎓-5-酸酯。由于三氟甲基酮和中性离子五元恶唑的存在，亲核试剂在C-1，C-5和三氟乙酰基上存在三个反应位点。基于该模型，三种模式发现苯肼的区域选择性攻击提供了三种不同的产物，分别以良好的产率提供了6-三氟甲基-1,2,4-三嗪3、3-三氟甲基-5-吡唑酮5和5-三氟甲基-3-羟基吡唑4。 ，取决于溶剂的性质和反应温度。
• Facile Synthesis of Imidazo[1,5-a]pyrazin-8(7H)-ones from Mesoionic 1,3-Oxazolium-5-olates via a Multistep One-Pot Transformation
  作者：Masami Kawase、Ryosuke Saijo、Hidemitsu Uno

  DOI：10.3987/com-16-13551

  日期：——

  A novel one-pot conversion of mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates into imidazo[1,5-a]pyrazin-8(7.H)-ones by the reaction with TosMIC is described. The structure of the product was determined by single-crystal X-ray analysis.
• Relative structure-inhibition analyses of the N-benzoyl and N-(phenylsulfonyl) amino acid aldose reductase inhibitors
  作者：Jack DeRuiter、R. Alan Davis、Vinay G. Wandrekar、Charles A. Mayfield

  DOI：10.1021/jm00111a030

  日期：1991.7

  A number of N-benzoyl amino acids were synthesized and tested to compare structure-inhibition relationships with the isosteric N-(phenylsulfonyl) amino acid (PS-amino acid) aldose reductase inhibitors. Inhibition analyses with these series reveals that their kinetic mechanisms of inhibition are similar, but that significant differences in structure-inhibition relationships exist. For example, while the PS-alanines and PS-2-phenylglycines produce enantioselective inhibition (S > R), no consistent pattern of enantioselectivity is observed with the isosteric N-benzoylalanines and 2-phenylglycines. Also, N-methyl and N-phenyl substitution in the PS-amino acid series does not substantially alter inhibitory activity, while similar substitutions in the N-benzoyl series (particularly N-phenyl) results in a significant increase in inhibitory activity. Proton NMR analysis of the N-benzoylsarcosines reveals that these compounds exist as a mixture of rotamers in solutions including the enzyme assay buffer and that the preferred conformer is one in which the carboxymethyl moiety is trans to the aromatic ring. Similar analyses with the N-benzoyl-N-phenylglycines demonstrate that these derivatives exist exclusively in the trans rotameric conformation in solution. No such N-substituent effects on conformation were observed in the PS-amino acid series. These results suggest that the differences in structure-inhibition trends between these structurally related series may result from the effect of substituents on preferred conformation.
• Heterocyclization of 4-Trifluoroacetyl-1,3-oxazolium-5-olates with 1,4-Bis-nucleophiles
  作者：Masami Kawase、Hiromi Koiwai、Toru Tanaka、Satoru Tani、Hiroshi Miyamae

  DOI：10.3987/com-01-9325

  日期：——

  Reactions of aromatic 1,4-bis-nucleophiles such as o-phenylenediamine and o-aminothiophenol, with mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1) gave regiospecifically seven member trifluoromethylated heterocycles such as 1,5-benzodiazepines (3) and 1,5-benzothiazepines (4). The reaction with o-aminophenol afforded non-cyclized products (5). The structures of 3, 4, and 5 were established by X-Ray diffraction analysis.