N-benzyl-N-(3,4-dimethoxyphenyl)-α-carbomethoxyacetamide | 155257-30-0

• 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: N-benzyl-N-(3,4-dimethoxyphenyl)-α-carbomethoxyacetamide
• 英文别名: methyl 3-(N-benzyl-3,4-dimethoxyanilino)-3-oxopropanoate
• CAS: 155257-30-0
• 化学式: C₁₉H₂₁NO₅
• 分子量: 343.379
• InChiKey: OMFDXQOHIKFCTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-(3,4-dimethoxyphenyl)-α-carbomethoxyacetamide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 甲烷磺酰基叠氮化物 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 20.5h， 生成 1,3-二氢-5-甲氧基-1-甲基-2H-吲哚-2-酮
  参考文献：
  名称：

  The Nafion-H Catalysed Cyclization of α-Carbomethoxy-α-Diazoacetanilides. Synthesis of 3-Unsubstituted-2-Indolinones.

  摘要：

  Diazoanilides of type 4 were found to undergo Nafion-H catalysed cyclization onto the aromatic ring and concomitant decarboxylation, under optimal conditions, to give 3-unsubstituted 2-indolinones 5 in moderate yields. Diazoanilides that possess electron-donating substituents in the aromatic moiety gave higher yields of 5 and, in one case, the presence of an electron-withdrawing group in the aromatic moiety did not impede the cyclization. In the case of the diazoanilides that possess a N-butenyl group, preferential 1,3-dipolar cycloaddition of the diazo unit onto the butenyl double bond occurred to give an unstable 1-pyrazoline which was converted, by loss of nitrogen accompanied by hydrogen migration, to dihydro-2-pyridinone derivatives. It was also found that substituents ortho to the amido group and/or the site of cyclization sterically retarded the cyclization.

  DOI：

  10.1016/s0040-4020(01)80781-x
• 作为产物：
  描述：

  甲基丙二酸氢 、 N-benzyl-3,4-dimethoxyaniline 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-benzyl-N-(3,4-dimethoxyphenyl)-α-carbomethoxyacetamide
  参考文献：
  名称：

  The Nafion-H Catalysed Cyclization of α-Carbomethoxy-α-Diazoacetanilides. Synthesis of 3-Unsubstituted-2-Indolinones.

  摘要：

  Diazoanilides of type 4 were found to undergo Nafion-H catalysed cyclization onto the aromatic ring and concomitant decarboxylation, under optimal conditions, to give 3-unsubstituted 2-indolinones 5 in moderate yields. Diazoanilides that possess electron-donating substituents in the aromatic moiety gave higher yields of 5 and, in one case, the presence of an electron-withdrawing group in the aromatic moiety did not impede the cyclization. In the case of the diazoanilides that possess a N-butenyl group, preferential 1,3-dipolar cycloaddition of the diazo unit onto the butenyl double bond occurred to give an unstable 1-pyrazoline which was converted, by loss of nitrogen accompanied by hydrogen migration, to dihydro-2-pyridinone derivatives. It was also found that substituents ortho to the amido group and/or the site of cyclization sterically retarded the cyclization.

  DOI：

  10.1016/s0040-4020(01)80781-x

文献信息

• NOVEL SUBSTITUTED DIAMINE DERIVATIVES USEFUL AS MOTILIN AGONISTS
  申请人：Johnson G. Sigmond

  公开号：US20070054888A1

  公开（公告）日：2007-03-08

  The present invention relates to novel substituted diamine derivatives for the formula wherein R 1 , R 2 , R 3 , R 4 , X 1 , X 2 , X 3 , X 4 , A, Y and n are as described in the specification, pharmaceutical compositions containing them and intermediates used in their manufacture. More particularly, the compounds of the invention are motilin receptor antagonists useful for the treatment of associated conditions and disorders such as gastrointestinal reflux disorders, eating disorders leading to obesity and irritable bowel syndrome.

  本发明涉及一种新的取代二胺衍生物，其化学式为R1，R2，R3，R4，X1，X2，X3，X4，A，Y和n如规范中所述，包含它们的制药组合物以及用于其制造的中间体。更具体地说，本发明的化合物是莫蒂林受体拮抗剂，可用于治疗相关疾病和疾病，如胃食管反流疾病，导致肥胖的进食障碍和肠易激综合征。
• US7166601B2
  申请人：——

  公开号：US7166601B2

  公开（公告）日：2007-01-23
• The Nafion-H Catalysed Cyclization of α-Carbomethoxy-α-Diazoacetanilides. Synthesis of 3-Unsubstituted-2-Indolinones.
  作者：Andrew G. Wee、Baosheng Liu

  DOI：10.1016/s0040-4020(01)80781-x

  日期：1994.1

  Diazoanilides of type 4 were found to undergo Nafion-H catalysed cyclization onto the aromatic ring and concomitant decarboxylation, under optimal conditions, to give 3-unsubstituted 2-indolinones 5 in moderate yields. Diazoanilides that possess electron-donating substituents in the aromatic moiety gave higher yields of 5 and, in one case, the presence of an electron-withdrawing group in the aromatic moiety did not impede the cyclization. In the case of the diazoanilides that possess a N-butenyl group, preferential 1,3-dipolar cycloaddition of the diazo unit onto the butenyl double bond occurred to give an unstable 1-pyrazoline which was converted, by loss of nitrogen accompanied by hydrogen migration, to dihydro-2-pyridinone derivatives. It was also found that substituents ortho to the amido group and/or the site of cyclization sterically retarded the cyclization.