Methyl 3-hydroxy-4-N-trifluoroacetylaminobenzoate | 131035-57-9

• 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: Methyl 3-hydroxy-4-N-trifluoroacetylaminobenzoate
• 英文别名: methyl 3-hydroxy-4-(2,2,2-trifluoroacetamido)benzoate；3-Hydroxy-4-trifluoracetamido-benzoesaeuremethylester；Methyl 3-hydroxy-4-[(2,2,2-trifluoroacetyl)amino]benzoate；methyl 3-hydroxy-4-[(2,2,2-trifluoroacetyl)amino]benzoate
• CAS: 131035-57-9
• 化学式: C₁₀H₈F₃NO₄
• 分子量: 263.173
• InChiKey: NQMULBPYHJWFBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Methyl 3-hydroxy-4-N-trifluoroacetylaminobenzoate 在 palladium on activated charcoal 盐酸 、 sodium nitrate 、 氢气 、 lanthanum(III) nitrate 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 8.0h， 生成 Methyl 2-amino-3-hydroxy-4-N-trifluoroacetylaminobenzoate
  参考文献：
  名称：

  Semi-synthesis of A.23187 (calcimycin) analogs with 5-n-amino substituents. Their complexation of calcium and magnesium

  摘要：

  The semi-synthesis of A.23187 (calcimycin) analogs 1-4 bearing the respective substituents: 5-NH2, 5-NHCH3, 5-N(CH3)2, 5-NHCOCH3 was carried out. The complexing properties of 1-4 for calcium and magnesium were determined by two-phase experiments (water/toluene-butanol 70:30 W/W) and found to be much weaker than these of A.23187 or X.14885A. There was a discrepancy with theoretical predictions made from model carboxybenzoxazoles.

  DOI：

  10.1016/s0040-4020(01)87824-8
• 作为产物：
  描述：

  3-羟基-4-硝基苯甲酸甲酯 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 26.0h， 生成 Methyl 3-hydroxy-4-N-trifluoroacetylaminobenzoate
  参考文献：
  名称：

  Semi-synthesis of A.23187 (calcimycin) analogs with 5-n-amino substituents. Their complexation of calcium and magnesium

  摘要：

  The semi-synthesis of A.23187 (calcimycin) analogs 1-4 bearing the respective substituents: 5-NH2, 5-NHCH3, 5-N(CH3)2, 5-NHCOCH3 was carried out. The complexing properties of 1-4 for calcium and magnesium were determined by two-phase experiments (water/toluene-butanol 70:30 W/W) and found to be much weaker than these of A.23187 or X.14885A. There was a discrepancy with theoretical predictions made from model carboxybenzoxazoles.

  DOI：

  10.1016/s0040-4020(01)87824-8

文献信息

• CH Oxygenation and<i>N</i>-Trifluoroacylation of Arylamines Under Metal-Free Conditions: A Convenient Approach to 2-Aminophenols and<i>N</i>-Trifluoroacyl-<i>ortho</i>-aminophenols
  作者：Vunnam Venkateswarlu、K. A. Aravinda Kumar、Shilpi Balgotra、G. Lakshma Reddy、M. Srinivas、Ram A. Vishwakarma、Sanghapal D. Sawant

  DOI：10.1002/chem.201402411

  日期：2014.5.26

  Direct ortho‐hydroxylation through CH oxygenation and N‐trifluoroacylation of anilines was achieved in a single step under metal‐free conditions by using a combination of TFA and oxone. The method allowed the formation of functionalised amino phenolic compounds such as ortho‐hydroxy‐N‐trifluoroacetanilides in good yields with broad substrate scope.

  通过在无金属条件下，通过使用TFA和过硫酸氢钾的组合，一步实现苯胺的CH 3 H氧化和N-三氟酰化直接邻羟基化。该方法可以形成功能化的氨基酚类化合物，例如邻-羟基-N-三氟乙酰苯胺，收率高，具有广泛的底物范围。
• Acid-promoted aromatic substitution processes in photochemical and thermal decompositions of aryl azides
  作者：Richard J. Sundberg、Kenneth B. Sloan

  DOI：10.1021/jo00951a018

  日期：1973.6
• Semi-synthesis of A.23187 (calcimycin) analogs with 5-n-amino substituents. Their complexation of calcium and magnesium
  作者：Fouzia Samih、Michelle Prudhomme、Gérard Dauphin、Georges Jeminet

  DOI：10.1016/s0040-4020(01)87824-8

  日期：1990.1

  The semi-synthesis of A.23187 (calcimycin) analogs 1-4 bearing the respective substituents: 5-NH2, 5-NHCH3, 5-N(CH3)2, 5-NHCOCH3 was carried out. The complexing properties of 1-4 for calcium and magnesium were determined by two-phase experiments (water/toluene-butanol 70:30 W/W) and found to be much weaker than these of A.23187 or X.14885A. There was a discrepancy with theoretical predictions made from model carboxybenzoxazoles.