ethyl 5-(1H-pyrrole-2-carboxamido)pentanoate | 334707-18-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 5-(1H-pyrrole-2-carboxamido)pentanoate
• 英文别名: ethyl 5-(1H-pyrrole-2-carbonylamino)pentanoate
• CAS: 334707-18-5
• 化学式: C₁₂H₁₈N₂O₃
• 分子量: 238.287
• InChiKey: WFOOVCOCBMOHSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 5-(1H-pyrrole-2-carboxamido)pentanoate 在 sodium hydroxide 、 2,4,6-三异丙基苯磺酰叠氮化物 、 水 、 溴 、 三乙胺 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 、 溶剂黄146 为溶剂， 生成 4,5-dibromo-N-[3-(1-methyl-2,5-dioxoimidazolidin-4-yl)propyl]-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  A convergent approach to midpacamide and dispacamide pyrrole-imidazole marine alkaloids

  摘要：

  A two-step synthesis of the N-acylated alpha -azido-omega -aminovalerate. a common intermediate for the synthesis of midpacamide and dispacamide, is described. This intermediate undergoes cyclization through the corresponding alpha -ureido ester derivative to give the 3-methylhydantoin ring present in midpacamide, whereas the reaction with triphenylphosphine. tosyl isocyanate and ammonia followed by cyclization of the resulting guanidine derivative provides the 2-aminoimidazole ring present in dispacamide. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02120-1
• 作为产物：
  描述：

  2-(三氯乙酰)吡咯 、 5-氨基戊酸乙酯盐酸盐 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以90%的产率得到ethyl 5-(1H-pyrrole-2-carboxamido)pentanoate
  参考文献：
  名称：

  An iminophosphorane-based approach for the synthesis of spiropyrrolidine–imidazole derivatives

  摘要：

  A method based on the reaction of an E-phosphazide, an intermediate in the Staudinger reaction between triphenylphosphine and an azide, with heterocumulenes allows the one-pot, two-component synthesis of a number of pyrrole-imidazole derivatives. The procedure, which involves sequential treatment of the appropriate a-azido ester with triphenylphosphine and isocyanate leads to the hydantoin product after aqueous work-up. The cyclization conditions can also be adapted for the synthesis of thiohydantoins by using isothiocyanates. These hybrids pyrrole-thiohydantoins undergo a novel oxidative spirocyclization by action of DDQ to give a tricyclic derivative (pyrrole-pyrrolidine-imidazole), which displays an interesting cytotoxic activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.12.021