ethyl N-methyl-N-(2-naphthyl)glycinate | 121810-70-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl N-methyl-N-(2-naphthyl)glycinate
• 英文别名: N-methyl-N-[2]naphthyl-glycine ethyl ester；N-Methyl-N-[2]naphthyl-glycin-aethylester；Ethyl 2-[methyl(naphthalen-2-yl)amino]acetate
• CAS: 121810-70-6
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: GIHVYUSUCLMIOO-UHFFFAOYSA-N

物化性质

• 沸点：
  165-170 °C(Press: 2 Torr)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl N-methyl-N-(2-naphthyl)glycinate 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 15.0h， 生成 4-pyridal (N-methyl-N-(2-naphthyl)glycinoyl)hydrazone
  参考文献：
  名称：

  Synthesis and antitubercular activity of N-(2-naphthyl)glycine hydrazide analogs

  摘要：

  N-(2-Naphthyl)glycine hydrazide analogues were synthesized and tested for possible in vitro antitubercular activity. N-(2-Naphthyl)alanine hydrazide (3), N-methyl-N-(2-naphthyl)glycine hydrazide (5), N-(6-methoxy-2-naphthyl)glycine hydrazide (7), and 3-(2-naphthylamino)butyric acid hydrazide (23) showed potent inhibitory action against Mycobacterium tuberculosis H37Rv in Youman's medium at concentrations ranging from 0.5 to 10.0 micrograms/mL. These compounds showed significant inhibitory action against isonicotinic acid hydrazide and streptomycin-resistant strains of M. tuberculosis. N-(6-Quinolyl)glycine hydrazide (18) and 3-(2-quinolylamino)butyric acid hydrazide (24), which are bioisosteres of compounds 1 and 23, showed loss of antitubercular activity at low concentrations.

  DOI：

  10.1021/jm00131a002
• 作为产物：
  描述：

  N-甲基-2-萘胺 、 氯乙酸乙酯 在 sodium acetate 作用下， 以 水 为溶剂， 反应 2.5h， 以82.3%的产率得到ethyl N-methyl-N-(2-naphthyl)glycinate
  参考文献：
  名称：

  Synthesis and antitubercular activity of N-(2-naphthyl)glycine hydrazide analogs

  摘要：

  N-(2-Naphthyl)glycine hydrazide analogues were synthesized and tested for possible in vitro antitubercular activity. N-(2-Naphthyl)alanine hydrazide (3), N-methyl-N-(2-naphthyl)glycine hydrazide (5), N-(6-methoxy-2-naphthyl)glycine hydrazide (7), and 3-(2-naphthylamino)butyric acid hydrazide (23) showed potent inhibitory action against Mycobacterium tuberculosis H37Rv in Youman's medium at concentrations ranging from 0.5 to 10.0 micrograms/mL. These compounds showed significant inhibitory action against isonicotinic acid hydrazide and streptomycin-resistant strains of M. tuberculosis. N-(6-Quinolyl)glycine hydrazide (18) and 3-(2-quinolylamino)butyric acid hydrazide (24), which are bioisosteres of compounds 1 and 23, showed loss of antitubercular activity at low concentrations.

  DOI：

  10.1021/jm00131a002

文献信息

• Photoredox-Catalyzed α-Aminomethyl Carboxylation of Styrenes with Sodium Glycinates: Synthesis of γ-Amino Acids and γ-Lactams
  作者：Cong Zhou、Miao Li、Jianwei Sun、Jiang Cheng、Song Sun

  DOI：10.1021/acs.orglett.1c00536

  日期：2021.4.16

  previous reactions with the same type of substrates leading to simple decarboxylation and olefin hydroalkylation, this process involves additional CO2 sequestration, thus leading to olefin α-aminomethyl carboxylation. These findings not only provide new access to α,α-disubstituted γ-amino acids and γ-lactams but also serve as a proof of concept for CO2 reutilization in decarboxylation reactions.

  已开发出一种可见光光氧化还原催化的苯乙烯与甘氨酸钠和 CO 2 的还原性α-氨基甲基羧化反应，以高效和区域选择性地合成一系列α,α-二取代 γ-氨基酸和 γ-内酰胺。值得注意的是，从脱羧步骤释放的CO 2可以重新用于随后的羧化。与之前使用相同类型底物导致简单脱羧和烯烃加氢烷基化的反应不同，该过程涉及额外的 CO 2封存，从而导致烯烃 α-氨基甲基羧化。这些发现不仅提供了对α,α-二取代的γ-氨基酸和γ-内酰胺，但也可作为脱羧反应中CO 2 再利用的概念证明。
• Synthetic Oxytocics. Derivatives of N-2-Naphthylglycine and N-2-Naphthyl-β-alanine^1,2
  作者：James E. Gearien、Kenneth J. Liska

  DOI：10.1021/ja01642a061

  日期：1954.7
• Direct Amination of γ-Halo-β-ketoesters with Anilines
  作者：Yinan Zhang、Richard B. Silverman

  DOI：10.1021/jo300239e

  日期：2012.4.6

  The direct amination of alpha-haloacetoacetates with anilines is described. Compared to existing methods, this simple protocol provides an attractive strategy to prepare diverse gamma-anilino-beta-ketoesters in one step. Good to excellent yields of the amination products were obtained under robust conditions, providing versatile and useful scaffolds.
• RAMAMURTHY, B.;BHATT, M. V., J. MED. CHEM., 32,(1989) N1, C. 2421-2426
  作者：RAMAMURTHY, B.、BHATT, M. V.

  DOI：——

  日期：——
• Synthesis and antitubercular activity of N-(2-naphthyl)glycine hydrazide analogs
  作者：B. Ramamurthy、M. V. Bhatt

  DOI：10.1021/jm00131a002

  日期：1989.11

  N-(2-Naphthyl)glycine hydrazide analogues were synthesized and tested for possible in vitro antitubercular activity. N-(2-Naphthyl)alanine hydrazide (3), N-methyl-N-(2-naphthyl)glycine hydrazide (5), N-(6-methoxy-2-naphthyl)glycine hydrazide (7), and 3-(2-naphthylamino)butyric acid hydrazide (23) showed potent inhibitory action against Mycobacterium tuberculosis H37Rv in Youman's medium at concentrations ranging from 0.5 to 10.0 micrograms/mL. These compounds showed significant inhibitory action against isonicotinic acid hydrazide and streptomycin-resistant strains of M. tuberculosis. N-(6-Quinolyl)glycine hydrazide (18) and 3-(2-quinolylamino)butyric acid hydrazide (24), which are bioisosteres of compounds 1 and 23, showed loss of antitubercular activity at low concentrations.