2-methoxy-5-oxo-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester | 1128263-43-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 2-methoxy-5-oxo-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 2-methoxy-5-oxo-2H-pyrrole-1-carboxylate
• CAS: 1128263-43-3
• 化学式: C₁₀H₁₅NO₄
• 分子量: 213.233
• InChiKey: OQKVLUXATAMEIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methoxy-5-oxo-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester 在 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 、 乙醚 、 环己烷 为溶剂， 反应 5.25h， 生成
  参考文献：
  名称：

  A facile synthesis of 5-alkoxypyrrol-2(5H)-ones using a modified aza-Achmatowicz oxidation

  摘要：

  An efficient approach to 2,4-disubstituted pyrroles has been uncovered and is based on an oxidative rearrangement of a furanyl carbamate followed by sequential reaction of the resulting 5-methoxypyrrol-2(5H)-one with various alkyl lithiates. The final step of the procedure involves heating the ring opened 1-methoxy-5-oxopentylcarbamate with a primary amine. The overall process can be carried out under mild conditions and complements existing methods to prepare 2,4-disubstituted pyrroles. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.011
• 作为产物：
  描述：

  2-furoyl azide 在 水 、 碘 、 碳酸氢钠 、 silver(l) oxide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 17.0h， 生成 2-methoxy-5-oxo-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  A facile synthesis of 5-alkoxypyrrol-2(5H)-ones using a modified aza-Achmatowicz oxidation

  摘要：

  An efficient approach to 2,4-disubstituted pyrroles has been uncovered and is based on an oxidative rearrangement of a furanyl carbamate followed by sequential reaction of the resulting 5-methoxypyrrol-2(5H)-one with various alkyl lithiates. The final step of the procedure involves heating the ring opened 1-methoxy-5-oxopentylcarbamate with a primary amine. The overall process can be carried out under mild conditions and complements existing methods to prepare 2,4-disubstituted pyrroles. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.03.011

文献信息

• Synthesis of 2,4-Disubstituted Pyrroles by Rearrangements of 2-Furanyl Carbamates
  作者：Sezgin Kiren、Xuechuan Hong、Carolyn A. Leverett、Albert Padwa

  DOI：10.1021/ol900059e

  日期：2009.3.19

  2,4-Disubstituted pyrroles were synthesized by an oxidative rearrangement of a furanyl carbamate followed by sequential reaction of the resulting 5-methoxypyrrol-2(5H)-one with different alkyl lithiates. The final step of the procedure involves heating the ring opened 1-methoxy-5-oxopentylcarbamate with a primary amine.

  通过呋喃基氨基甲酸酯的氧化重排，然后使所得的5-甲氧基吡咯-2（5 H）-one与不同的烷基锂酸酯顺序反应，合成了2,4-二取代的吡咯。该方法的最后步骤涉及将开环的1-甲氧基-5-氧戊基氨基甲酸酯与伯胺一起加热。