2-(1,1-diethoxyethyl)-1-pyrroline | 176449-54-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1,1-diethoxyethyl)-1-pyrroline
• 英文别名: 5-(1,1-diethoxyethyl)-3,4-dihydro-2H-pyrrole
• CAS: 176449-54-0
• 化学式: C₁₀H₁₉NO₂
• 分子量: 185.266
• InChiKey: OWTWOMGXNZRACL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1,1-diethoxyethyl)-1-pyrroline 在 盐酸 作用下， 反应 48.0h， 生成 2-乙酰基-1-吡咯啉 、 3(4H)-吡啶酮,5,6-二氢-2-甲基-
  参考文献：
  名称：

  Novel Syntheses of the Major Flavor Components of Bread and Cooked Rice

  摘要：

  A new synthetic pathway toward the Maillard flavor compounds 6-acyl-1,2,3,4-tetrahydropyridines and 2-acetyl-1-pyrroline is presented. The reaction sequence involves deprotonation of a vicinal diimine and subsequent alkylation with an N,N-diprotected omega-bromoalkylamine, followed by deprotection and intramolecular transimination of the functionalized intermediate. Acidic workup affords the above-mentioned heterocycles, which are principal flavor constituents of bread and cooked rice, respectively. In addition, the synthesis of the more stable diethyl acetal of 2-acetyl-1-pyrroline is described.

  DOI：

  10.1021/jf950728c
• 作为产物：
  描述：

  N-(3,3-diethoxy-2-butylidene)ispropylamine 在 草酸 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 23.0h， 生成 2-(1,1-diethoxyethyl)-1-pyrroline
  参考文献：
  名称：

  Novel Syntheses of the Major Flavor Components of Bread and Cooked Rice

  摘要：

  A new synthetic pathway toward the Maillard flavor compounds 6-acyl-1,2,3,4-tetrahydropyridines and 2-acetyl-1-pyrroline is presented. The reaction sequence involves deprotonation of a vicinal diimine and subsequent alkylation with an N,N-diprotected omega-bromoalkylamine, followed by deprotection and intramolecular transimination of the functionalized intermediate. Acidic workup affords the above-mentioned heterocycles, which are principal flavor constituents of bread and cooked rice, respectively. In addition, the synthesis of the more stable diethyl acetal of 2-acetyl-1-pyrroline is described.

  DOI：

  10.1021/jf950728c

文献信息

• Novel Syntheses of the Major Flavor Components of Bread and Cooked Rice
  作者：Norbert De Kimpe、Marian Keppens

  DOI：10.1021/jf950728c

  日期：1996.1.1

  A new synthetic pathway toward the Maillard flavor compounds 6-acyl-1,2,3,4-tetrahydropyridines and 2-acetyl-1-pyrroline is presented. The reaction sequence involves deprotonation of a vicinal diimine and subsequent alkylation with an N,N-diprotected omega-bromoalkylamine, followed by deprotection and intramolecular transimination of the functionalized intermediate. Acidic workup affords the above-mentioned heterocycles, which are principal flavor constituents of bread and cooked rice, respectively. In addition, the synthesis of the more stable diethyl acetal of 2-acetyl-1-pyrroline is described.