methyl 3-acetamido-3-(1-phenyl-1H-pyrrol-2-yl)propanoate | 1445609-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 3-acetamido-3-(1-phenyl-1H-pyrrol-2-yl)propanoate
• 英文别名: Methyl 3-acetamido-3-(1-phenylpyrrol-2-yl)propanoate；methyl 3-acetamido-3-(1-phenylpyrrol-2-yl)propanoate
• CAS: 1445609-07-3
• 化学式: C₁₆H₁₈N₂O₃
• 分子量: 286.331
• InChiKey: HNXFFUWNINVQKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 2-(5-acetyl-2-phenyl-3-oxa-2,5-diazabicyclo[2.2.2]oct-7-en-6-yl)acetate 在 copper(l) chloride 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以72%的产率得到methyl 3-acetamido-3-(1-phenyl-1H-pyrrol-2-yl)propanoate
  参考文献：
  名称：

  由苯基亚硝基Diels-Alder加合物与1,2-二氢吡啶合成受保护的（1-Phenyl-1 H-吡咯-2-基）-烷烃-1-胺

  摘要：

  用适当保护的1，2-二氢吡啶对亚硝基苯衍生的环加合物进行还原性裂解，可以新颖，简单地获得取代的N- [1-（1-苯基-1 H-吡咯-2-基）烷基酰胺。该合成还可以以非常简单，温和和实用的一锅法进行，而无需借助催化量的CuCl分离相应的亚硝基苯环加合物。

  DOI：

  10.1021/jo4009996

文献信息

• Synthesis of 2,7-Diazabicyclo[2.2.1]heptenes by N–O Bond Cleavage of Arylnitroso Diels–Alder 1,2-Dihydropyridine Cycloadducts
  作者：Mauro Pineschi、Francesco Berti、Valeria Di Bussolo

  DOI：10.1055/s-0034-1378682

  日期：——

  The cleavage of the N-O bond of nitrosoarene-derived cycloadducts with 1,2-dihydropyridines gives different products depending on the protecting group of the starting dihydropyridine and reaction conditions. The use of catalytic amounts of CuCl in non-nucleophilic solvents in combination with a N-phenoxycarbonyl-protected nitrosophenyl-derived cycloadduct allowed the unprecedented formation of the 2,7-diazabicycle[2.2.1]heptene scaffold. It was also demonstrated that this novel bicyclic gem-diamine derivative is an isolable intermediate en route to pyrrole derivatives. On the other hand, the corresponding nitrosopyridine-derived cycloadduct showed to be unreactive with copper salts, but the application of different reductive conditions can deliver the corresponding bicyclic gem-diamine derivative or 3-aminotetrahydropyridine also in enantioenriched form.
• Synthesis of Protected (1-Phenyl-1<i>H</i>-pyrrol-2-yl)-alkane-1-amines from Phenylnitroso Diels–Alder Adducts with 1,2-Dihydropyridines
  作者：Francesco Berti、Valeria Di Bussolo、Mauro Pineschi

  DOI：10.1021/jo4009996

  日期：2013.7.19

  The reductive cleavage of nitrosobenzene-derived cycloadducts with appropriately protected 1,2-dihydropyridines allows a novel and simple obtainment of substituted N-[1-(1-phenyl-1H-pyrrol-2-yl)alkylamides. This synthesis can also be carried out in a very simple, mild, and practical one-pot procedure without isolation of the corresponding nitrosobenzene cycloadduct by means of catalytic amounts of

  用适当保护的1，2-二氢吡啶对亚硝基苯衍生的环加合物进行还原性裂解，可以新颖，简单地获得取代的N- [1-（1-苯基-1 H-吡咯-2-基）烷基酰胺。该合成还可以以非常简单，温和和实用的一锅法进行，而无需借助催化量的CuCl分离相应的亚硝基苯环加合物。