methyl 2-((4-methoxyphenyl)(methyl)amino)benzoate | 1541201-68-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: methyl 2-((4-methoxyphenyl)(methyl)amino)benzoate
• 英文别名: methyl 2-(4-methoxy-N-methylanilino)benzoate
• CAS: 1541201-68-6
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: MHKDYPMNYQROKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-((4-methoxyphenyl)(methyl)amino)benzoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 [2-(4-methoxy-N-methylanilino)phenyl]methanol
  参考文献：
  名称：

  PhI(OAc)₂-Mediated Intramolecular Oxidative Aryl-Aldehyde Csp²–Csp² Bond Formation: Metal-Free Synthesis of Acridone Derivatives

  摘要：

  A metal-free protocol for direct aryl-aldehyde Csp(2)-Csp(2) bond formation via a PhI(OAc)2-mediated intramolecular cross-dehydrogenative coupling (CDC) of various 2-(N-arylamino)aldehydes was developed. The novel methodology requires no need of preactivation of the aldehyde group, is applicable to a large variety of functionalized substrates, and most of all provides a convenient approach to the construction of biologically important acridone derivatives.

  DOI：

  10.1021/jo5011697
• 作为产物：
  描述：

  2-碘苯甲酸 在 N-甲基吗啉 、 copper(I) oxide 、 sodium hydride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 3.5h， 生成 methyl 2-((4-methoxyphenyl)(methyl)amino)benzoate
  参考文献：
  名称：

  PhI(OAc)₂-Mediated Intramolecular Oxidative Aryl-Aldehyde Csp²–Csp² Bond Formation: Metal-Free Synthesis of Acridone Derivatives

  摘要：

  A metal-free protocol for direct aryl-aldehyde Csp(2)-Csp(2) bond formation via a PhI(OAc)2-mediated intramolecular cross-dehydrogenative coupling (CDC) of various 2-(N-arylamino)aldehydes was developed. The novel methodology requires no need of preactivation of the aldehyde group, is applicable to a large variety of functionalized substrates, and most of all provides a convenient approach to the construction of biologically important acridone derivatives.

  DOI：

  10.1021/jo5011697

文献信息

• Construction of 1,4-Benzodiazepine Skeleton from 2-(Arylamino)benzamides through PhI(OAc)₂-Mediated Oxidative C–N Bond Formation
  作者：Xuming Li、Liu Yang、Xiang Zhang、Daisy Zhang-Negrerie、Yunfei Du、Kang Zhao

  DOI：10.1021/jo402413g

  日期：2014.2.7

  the biologically important 1,4-benzodiazepine skeleton were conveniently constructed from 2-(arylamino)benzamides through PhI(OAc)2-mediated oxidative C–N bond formation. The attractive features of this new synthetic strategy include mild reaction conditions, the heavy-metal-free characteristic of the oxidative coupling process, and the flexibility to tolerate a broad scope of substrates.

  由2-（芳基氨基）苯甲酰胺通过PhI（OAc）2介导的氧化性C–N键形成，可方便地构建涉及具有重要生物学意义的1,4-苯并二氮杂skeleton骨架的新化合物。这种新的合成策略的吸引人的特征包括温和的反应条件，氧化偶联过程的不含重金属的特性以及可耐受广泛范围底物的灵活性。
• Substrate-Controlled Selectivity Switch in the Three-Component Coupling Involving Arynes, Aromatic Tertiary Amines, and CO₂
  作者：Sachin Suresh Bhojgude、Tony Roy、Rajesh G. Gonnade、Akkattu T. Biju

  DOI：10.1021/acs.orglett.6b02845

  日期：2016.10.21

  The transition-metal-free multicomponent coupling involving arynes, aromatic tertiary amines, and CO2 is reported. The reaction exhibits switchable selectivity depending on the electronic nature of the aromatic amines used. With amines bearing electron-releasing/neutral groups as the nucleophilic trigger, the reaction afforded 2-arylamino benzoates via a nitrogen to oxygen alkyl group migration. Employing

  报道了涉及芳烃，芳族叔胺和CO 2的无过渡金属的多组分偶联。反应显示出可切换的选择性，这取决于所用芳族胺的电子性质。使用带有电子释放/中性基团的胺作为亲核触发物，该反应通过氮到氧的烷基迁移提供了2-芳基氨基苯甲酸酯。在该反应中使用缺电子的胺提供了2-氨基芳基苯甲酸酯，其通过芳基至芳基氨基的迁移进行，类似于Smiles重排。