methyl 5-(azidomethyl)-1-benzyl-2-methyl-4,5-dihydro-1H-pyrrole-3-carboxylate | 951317-37-6

• 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 5-(azidomethyl)-1-benzyl-2-methyl-4,5-dihydro-1H-pyrrole-3-carboxylate
• CAS: 951317-37-6
• 化学式: C₁₅H₁₈N₄O₂
• 分子量: 286.334
• InChiKey: ROCGFZARZPLGMR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  78.3
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 5-(azidomethyl)-1-benzyl-2-methyl-4,5-dihydro-1H-pyrrole-3-carboxylate 在 Lindlar's catalyst 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、344.75 kPa 条件下， 以70%的产率得到methyl 5-(aminomethyl)-1-benzyl-2-methyl-4,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Synthesis of pyrrolidine-substituted benzamides via iodocyclization of β-enaminoesters

  摘要：

  Novel 2-, and N-substituted 5-methylene-pyrrolidine benzamides and 2-, 3-, and N-substituted 5-methylene-2-pyrroline benzamides were synthesized for the first time in a straightforward manner and in good yields via iodocyclization of gamma- and alpha-alkenyl-beta-enaminoesters, respectively. The key step in the process is the synthesis of the methylene-pyrrolidine iodide and methylene-2-pyrroline iodide intermediates. Functional group inter-conversion of these iodides to their amino analogs, and their subsequent coupling to benzoic acids via EDC, afforded the above pyrrolidine/2-pyrroline-substituted benzamides in yields of around 75%. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.166
• 作为产物：
  描述：

  2-乙酰基戊-4-烯酸甲酯 在 aluminum oxide 、 sodium azide 、 四乙基溴化铵 、 碘 、 碳酸氢钠 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 methyl 5-(azidomethyl)-1-benzyl-2-methyl-4,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Synthesis of pyrrolidine-substituted benzamides via iodocyclization of β-enaminoesters

  摘要：

  Novel 2-, and N-substituted 5-methylene-pyrrolidine benzamides and 2-, 3-, and N-substituted 5-methylene-2-pyrroline benzamides were synthesized for the first time in a straightforward manner and in good yields via iodocyclization of gamma- and alpha-alkenyl-beta-enaminoesters, respectively. The key step in the process is the synthesis of the methylene-pyrrolidine iodide and methylene-2-pyrroline iodide intermediates. Functional group inter-conversion of these iodides to their amino analogs, and their subsequent coupling to benzoic acids via EDC, afforded the above pyrrolidine/2-pyrroline-substituted benzamides in yields of around 75%. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.166