1-carbamoyl-2-methyl-pyrrole-3-carboxylic acid ethyl ester | 54449-03-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-carbamoyl-2-methyl-pyrrole-3-carboxylic acid ethyl ester
• 英文别名: Ethyl 1-carbamoyl-2-methylpyrrole-3-carboxylate
• CAS: 54449-03-5
• 化学式: C₉H₁₂N₂O₃
• 分子量: 196.206
• InChiKey: DBRNMEHLXHUECU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-carbamoyl-2-methyl-pyrrole-3-carboxylic acid ethyl ester 、 氰化钾 、 乙醇 以72%的产率得到
  参考文献：
  名称：

  ASHBY J.; GRIFFITHS D., J. CHEM. SOC. PERKIN TRANS. , 1975, PART 1, NO 7, 657-662

  摘要：

  DOI：
• 作为产物：
  描述：

  Ethyl 2-(carbamoylamino)-5-methyl-2,3-dihydrofuran-4-carboxylate 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 1.33h， 以69%的产率得到1-carbamoyl-2-methyl-pyrrole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Unexpected pathway of the reaction of N-[(β-halogeno-α-tosyl)alkyl]ureas with β-oxoester enolates. Synthesis of ethyl 5-ureido-4,5-dihydrofuran-3-carboxylates and N-carbamoylpyrrole-3-carboxylates

  摘要：

  Reaction of beta-halogeno-alpha-tosyl-substituted N-alkylureas with sodium enolates of beta-oxoesters proceeds predominantly via nucleophilic substitution of the halogen rather than the tosyl group followed by spontaneous cyclization to give ethyl 5-ureido-4,5-dihydrofuran-3-carboxylates. The latter are transformed into ethyl N-carbamoylpyrrole-3-carboxylates under acidic conditions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.162

文献信息

• BULLOCK E.; CARTER R. A.; COCHRANE R. M.; GREGORY B.; SHIELDS D. C., CAN. J. CHEM. <CJCH-AG>, 1977, 55, NO 5, 895-905
  作者：BULLOCK E.、 CARTER R. A.、 COCHRANE R. M.、 GREGORY B.、 SHIELDS D. C.

  DOI：——

  日期：——
• Unexpected pathway of the reaction of N-[(β-halogeno-α-tosyl)alkyl]ureas with β-oxoester enolates. Synthesis of ethyl 5-ureido-4,5-dihydrofuran-3-carboxylates and N-carbamoylpyrrole-3-carboxylates
  作者：Nikolay N. Kurochkin、Anastasia A. Fesenko、Dmitry A. Cheshkov、Musa M. Davudi、Anatoly D. Shutalev

  DOI：10.1016/j.tetlet.2010.10.162

  日期：2011.1

  Reaction of beta-halogeno-alpha-tosyl-substituted N-alkylureas with sodium enolates of beta-oxoesters proceeds predominantly via nucleophilic substitution of the halogen rather than the tosyl group followed by spontaneous cyclization to give ethyl 5-ureido-4,5-dihydrofuran-3-carboxylates. The latter are transformed into ethyl N-carbamoylpyrrole-3-carboxylates under acidic conditions. (C) 2010 Elsevier Ltd. All rights reserved.
• ASHBY J.; GRIFFITHS D., J. CHEM. SOC. PERKIN TRANS. <JCPK-BH>, 1975, PART 1, NO 7, 657-662
  作者：ASHBY J.、 GRIFFITHS D.

  DOI：——

  日期：——