ethyl 2-((2-fluoro-4-methylphenyl)amino)-2-oxoacetate | 1182998-66-8

• 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 2-((2-fluoro-4-methylphenyl)amino)-2-oxoacetate
• 英文别名: Ethyl 2-(2-fluoro-4-methylanilino)-2-oxoacetate
• CAS: 1182998-66-8
• 化学式: C₁₁H₁₂FNO₃
• 分子量: 225.22
• InChiKey: CMGWVTQOMJKUPQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.254±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-((2-fluoro-4-methylphenyl)amino)-2-oxoacetate 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-(2-Fluoro-4-methylanilino)-2-oxoacetic acid
  参考文献：
  名称：

  Design, Synthesis, and Antiviral Activity of Entry Inhibitors That Target the CD4-Binding Site of HIV-1

  摘要：

  The CD4 binding site on HIV-1 gp120 has been validated as a drug target to prevent HIV-1 entry to cells. Previously, we identified two small molecule inhibitors consisting of a 2,2,6,6-tetramethylpiperidine ring linked by an oxalamide to a p-halide-substituted phenyl group, which target this site, specifically, a cavity termed "Phe43 cavity". Here we use synthetic chemistry, functional assessment, and structure-based analysis to explore variants of each region of these inhibitors for improved antiviral properties. Alterations of the phenyl group and of the oxalamide linker indicated that these regions were close to optimal in the original lead compounds. Design of a series of compounds, where the tetramethylpiperidine ring was replaced with new scaffolds, led to improved antiviral activity. These new scaffolds provide insight into the surface chemistry at the entrance of the cavity and offer additional opportunities by which to optimize further these potential-next-generation therapeutics and microbicides against HIV-1.

  DOI：

  10.1021/jm3002247
• 作为产物：
  描述：

  2-氟-4-甲基苯胺 、 草酰氯单乙酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 ethyl 2-((2-fluoro-4-methylphenyl)amino)-2-oxoacetate
  参考文献：
  名称：

  Design, Synthesis, and Antiviral Activity of Entry Inhibitors That Target the CD4-Binding Site of HIV-1

  摘要：

  The CD4 binding site on HIV-1 gp120 has been validated as a drug target to prevent HIV-1 entry to cells. Previously, we identified two small molecule inhibitors consisting of a 2,2,6,6-tetramethylpiperidine ring linked by an oxalamide to a p-halide-substituted phenyl group, which target this site, specifically, a cavity termed "Phe43 cavity". Here we use synthetic chemistry, functional assessment, and structure-based analysis to explore variants of each region of these inhibitors for improved antiviral properties. Alterations of the phenyl group and of the oxalamide linker indicated that these regions were close to optimal in the original lead compounds. Design of a series of compounds, where the tetramethylpiperidine ring was replaced with new scaffolds, led to improved antiviral activity. These new scaffolds provide insight into the surface chemistry at the entrance of the cavity and offer additional opportunities by which to optimize further these potential-next-generation therapeutics and microbicides against HIV-1.

  DOI：

  10.1021/jm3002247

文献信息

• TBAI-Catalyzed S–H and N–H Insertion Reactions of α-Diazoesters with Thiophenols and Amines under Metal-Free Conditions
  作者：Rongxiang Chen、Guoyang Ma、Yawen Li、Jinju Zhang、Ran Xia、Kai-Kai Wang、Lantao Liu

  DOI：10.1021/acs.joc.2c01262

  日期：2022.8.19

  Mild, convenient, and effective TBAI-catalyzed S–H and N–H insertion reactions of α-diazoesters with thiophenols and aromatic amines under metal-free conditions have been described, furnishing a straightforward and general platform for the synthesis of various thioethers and 2-amino-2-oxoacetates in moderate to excellent yields. Moreover, this strategy features simple operation, mild conditions, broad

  已经描述了在无金属条件下温和、方便和有效的 TBAI 催化的 α-重氮酯与苯硫酚和芳香胺的 S-H 和 N-H 插入反应，为合成各种硫醚和 2 -amino-2-oxoacetates，产率适中至极好。此外，该策略具有操作简单、条件温和、底物范围广、易于放大等特点。