methyl 4,5-dimethyl-2-(methyl(phenyl)amino)benzoate | 1428865-17-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: methyl 4,5-dimethyl-2-(methyl(phenyl)amino)benzoate
• CAS: 1428865-17-1
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: OJDVWWBVMGEHQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 4,5-dimethyl-2-(methyl(phenyl)amino)benzoate 在 lithium aluminium tetrahydride 、 sodium sulfate 、 scandium tris(trifluoromethanesulfonate) 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 2,3,10-trimethyl-10H-acridin-9-one
  参考文献：
  名称：

  Sc(OTf)₃-Catalyzed Dehydrogenative Cyclization for Synthesis of N-Methylacridones

  摘要：

  A novel method has been developed for the synthesis of substituted N-methylacridones from 2-(N-methyl-N-phenylamino)benzaldehydes via dehydrogenative cyclization. This transformation involves two primary processes: the aldehyde first coordinates with Sc(OTf)(3) and induces the aromatic electrophilic substitution (SEAr) reaction to form the active intermediate N-methyl-acridin-9-ol, which is then quickly oxidized in situ to afford the acridones. Furthermore, the procedure involved is both environmental friendly and atom efficient; H2O is the only byproduct in this reaction.

  DOI：

  10.1021/ol400371h
• 作为产物：
  描述：

  苯胺 在 copper diacetate 、 sodium acetate 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.25h， 生成 methyl 4,5-dimethyl-2-(methyl(phenyl)amino)benzoate
  参考文献：
  名称：

  Sc(OTf)₃-Catalyzed Dehydrogenative Cyclization for Synthesis of N-Methylacridones

  摘要：

  A novel method has been developed for the synthesis of substituted N-methylacridones from 2-(N-methyl-N-phenylamino)benzaldehydes via dehydrogenative cyclization. This transformation involves two primary processes: the aldehyde first coordinates with Sc(OTf)(3) and induces the aromatic electrophilic substitution (SEAr) reaction to form the active intermediate N-methyl-acridin-9-ol, which is then quickly oxidized in situ to afford the acridones. Furthermore, the procedure involved is both environmental friendly and atom efficient; H2O is the only byproduct in this reaction.

  DOI：

  10.1021/ol400371h

文献信息

• 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。