ethyl 5-(1H-pyrrole-2-carboxamido)-2-azidopentanoate | 334707-19-6

• 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)-2-azidopentanoate
• 英文别名: ethyl 2-azido-5-(1H-pyrrole-2-carbonylamino)pentanoate
• CAS: 334707-19-6
• 化学式: C₁₂H₁₇N₅O₃
• 分子量: 279.299
• InChiKey: PTQGVLXZGASMRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 5-(1H-pyrrole-2-carboxamido)-2-azidopentanoate 以 乙醚 为溶剂， 反应 60.0h， 生成 N-[3-(1-ethyl-5-oxo-2-sulfanylideneimidazolidin-4-yl)propyl]-1H-pyrrole-2-carboxamide
  参考文献：
  名称：

  Trapping of a phosphazide intermediate in the Staudinger reaction of tertiary phosphines with azides and its application to the synthesis of analogs of the marine alkaloid midpacamide

  摘要：

  A new method based on the reaction of an E-phosphazide, ail intermediate in the Staudinger reaction between triphenylphosphine with an azide, with heterocumulenes allows the one-pot, two-component synthesis of a number of analogs of the pyrrole-imidazole marine alkaloid midpacamide. The procedure, which involves sequential treatment of the appropriate alpha-azido ester with triphenylphosphine and isothiocyanate leads to the thiohydantoin product after aqueous workup. The cyclization conditions call also be adapted to the synthesis of hydantoins by using isocyanates. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.117
• 作为产物：
  描述：

  2-(三氯乙酰)吡咯 在 正丁基锂 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 26.0h， 生成 ethyl 5-(1H-pyrrole-2-carboxamido)-2-azidopentanoate
  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

文献信息

• Trapping of a phosphazide intermediate in the Staudinger reaction of tertiary phosphines with azides and its application to the synthesis of analogs of the marine alkaloid midpacamide
  作者：Pilar M. Fresneda、Marta Castañeda、Miguel A. Sanz、Pedro Molina

  DOI：10.1016/j.tetlet.2003.12.117

  日期：2004.2

  A new method based on the reaction of an E-phosphazide, ail intermediate in the Staudinger reaction between triphenylphosphine with an azide, with heterocumulenes allows the one-pot, two-component synthesis of a number of analogs of the pyrrole-imidazole marine alkaloid midpacamide. The procedure, which involves sequential treatment of the appropriate alpha-azido ester with triphenylphosphine and isothiocyanate leads to the thiohydantoin product after aqueous workup. The cyclization conditions call also be adapted to the synthesis of hydantoins by using isocyanates. (C) 2004 Elsevier Ltd. All rights reserved.
• A convergent approach to midpacamide and dispacamide pyrrole-imidazole marine alkaloids
  作者：Pilar M Fresneda、Pedro Molina、Miguel A Sanz

  DOI：10.1016/s0040-4039(00)02120-1

  日期：2001.1

  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.
• An iminophosphorane-based approach for the synthesis of spiropyrrolidine–imidazole derivatives
  作者：Pilar M. Fresneda、Marta Castañeda、Miguel Angel Sanz、Delia Bautista、Pedro Molina

  DOI：10.1016/j.tet.2006.12.021

  日期：2007.2

  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.