methyl 3-(2-aminophenylamino)-benzoate | 1189178-14-0

• 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-(2-aminophenylamino)-benzoate
• 英文别名: Methyl 3-[(2-Aminophenyl)amino]benzoate；methyl 3-(2-aminoanilino)benzoate
• CAS: 1189178-14-0
• 化学式: C₁₄H₁₄N₂O₂
• 分子量: 242.277
• InChiKey: GNHSCCPWKBBPKT-UHFFFAOYSA-N

物化性质

• 沸点：
  398.9±27.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-(2-aminophenylamino)-benzoate 在 氯化亚砜 、 caesium carbonate 、 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 12.0h， 生成 (S)-2-(3-(1H-benzo[d]imidazol-1-yl)phenyl)-4-tert-butyl-4,5-dihydrooxazole
  参考文献：
  名称：

  Synthesis of Novel N-Heterocyclic Carbene-Oxazoline Palladium Complexes and Their Applications in Suzuki-Miyaura Cross-Coupling Reaction

  摘要：

  A series of novel N-heterocyclic carbene-oxazoline ligands were synthesized in six steps. Palladium complexes were obtained by deprotonation of the benzimidazole salts and subsequent ligation with Pd(OAc)(2) in THF. Different types of cyclic bis- and tetrapalladium complexes were achieved by modifying substituent of oxazoline group. The structures of these palladium complexes were characterized by NMR and X-ray diffraction analysis. Catalytic properties of these Pd-complexes were tested by Suzuki-Miyaura cross-coupling reaction.

  DOI：

  10.1055/s-0033-1338848
• 作为产物：
  描述：

  methyl 3-(2-nitrophenylamino)-benzoate 在 10% palladium on activated carbon 、 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以75%的产率得到methyl 3-(2-aminophenylamino)-benzoate
  参考文献：
  名称：

  有效的二苯甲enza庚因基作为β-分泌酶抑制剂的设计与合成

  摘要：

  我们已经确定了小分子二苯并pine庚因的β-分泌酶抑制剂（BACE1）。这些BACE1抑制剂具有两个关键的显着特征。第一个是与两个代表P3-P2残基的芳环稠合的七元杂环。第二个是代表P1'残基的酰胺和/或酰胺生物等排体。合理的优化导致了有效的类似物的鉴定，例如10（K I = 211 nM）。

  DOI：

  10.1021/jm9008482

文献信息

• Rational Design and Synthesis of Potent Dibenzazepine Motifs as β-Secretase Inhibitors
  作者：Taleb H. Al-Tel、Raed A. Al-Qawasmeh、Marco F. Schmidt、Amal Al-Aboudi、Shashidhar N. Rao、Salim S. Sabri、Wolfgang Voelter

  DOI：10.1021/jm9008482

  日期：2009.10.22

  identified small-molecule dibenzazepine inhibitors of β-secretase (BACE1). These BACE1 inhibitors possess two key salient features. The first is a seven-membered heterocyclic ring fused to two aromatic rings representing the P3−P2 residues. The second is an amide and/or amide bioisostere representing the P1′ residue. Rational optimization led to the identification of potent analogues, such as 10 (KI = 211

  我们已经确定了小分子二苯并pine庚因的β-分泌酶抑制剂（BACE1）。这些BACE1抑制剂具有两个关键的显着特征。第一个是与两个代表P3-P2残基的芳环稠合的七元杂环。第二个是代表P1'残基的酰胺和/或酰胺生物等排体。合理的优化导致了有效的类似物的鉴定，例如10（K I = 211 nM）。
• Synthesis of Novel N-Heterocyclic Carbene-Oxazoline Palladium Complexes and Their Applications in Suzuki-Miyaura Cross-Coupling Reaction
  作者：Qin Xu、Min Shi、Peng Gu

  DOI：10.1055/s-0033-1338848

  日期：——

  A series of novel N-heterocyclic carbene-oxazoline ligands were synthesized in six steps. Palladium complexes were obtained by deprotonation of the benzimidazole salts and subsequent ligation with Pd(OAc)(2) in THF. Different types of cyclic bis- and tetrapalladium complexes were achieved by modifying substituent of oxazoline group. The structures of these palladium complexes were characterized by NMR and X-ray diffraction analysis. Catalytic properties of these Pd-complexes were tested by Suzuki-Miyaura cross-coupling reaction.