diethyl 2-nitropyrrole-3,4-dicarboxylate | 54760-18-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: diethyl 2-nitropyrrole-3,4-dicarboxylate
• 英文别名: 2-nitro-pyrrole-3,4-dicarboxylic acid diethyl ester；diethyl 2-nitro-1H-pyrrole-3,4-dicarboxylate
• CAS: 54760-18-8
• 化学式: C₁₀H₁₂N₂O₆
• 分子量: 256.215
• InChiKey: AFXGAPMALHEANU-UHFFFAOYSA-N

物化性质

• 沸点：
  450.0±40.0 °C(Predicted)
• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 2-nitropyrrole-3,4-dicarboxylate 在 氨 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 288.0h， 生成 2-nitro-1-[2-(2-pyridyl)ethyl]pyrrole-3,4-dicarboxamide
  参考文献：
  名称：

  2-硝基吡咯-3,4-二甲酰胺的高效合成

  摘要：

  摘要 N-1-取代的 2-硝基吡咯-3,4-二甲酰胺 (4-5, 7-9) 的合成是由 2-硝基吡咯-3,4-二甲酸二乙酯 (2) 合成的。2-硝基-吡咯-3,4-二甲酰胺(1)通过2-硝基-1-[2-(2-吡啶基)乙基]吡咯-3,4-二甲酰胺(9)的脱保护制备。化合物9是通过两种不同的方法获得的。

  DOI：

  10.1080/00397919908086015

文献信息

• Synthesis and Unusual Chemical Reactivity of Certain Novel 4,5-Disubstituted 7-Benzylpyrrolo[2,3-<i>d</i>][1,2,3]triazines
  作者：Michael T. Migawa、Leroy B. Townsend

  DOI：10.1021/jo001499i

  日期：2001.7.1

  The fact that only two pyrrolo[2,3-d] [1,2,3]triazines heterocycles had been reported in the literature prompted us to initiate studies designed to provide additional members of this ring system. Initial attempts to prepare additional derivatives of the 7-unsubstituted pyrrolo[2,3-d] [1,2,3]triazin-4-ones were limited by their low chemical reactivity. Subsequently, 7-benzyl-5-carboxamidopyrrololo-,3-d] [1,2,3]triazin-4-one (16) was prepared from diethyl 2-nitropyrrole-3,4,-dicarboxylate via an alkylation, ammonolysis, reduction and intramolecular diazocoupling sequence. Conversion of 16 into 7-benzyl-4-( 1,2,4-triazol-1-yl)pyrrolo [2,3-d] [1,2,3]triazine-5-carbonitrile (17) was accomplished, and nucleophilic displacements of the 4-triazol-1- yl group were studied. Treatment of 17 with NH3/CH3CN gave a mixture of 4-amino-7-benzylpyrrolo [2,3-d] [1,2,3] triazine-5-carbonitrile (19) and 2-amino-1-benzylpyrrole-3,4-dicarbonitrile (21), A mechanism to account for the formation of this mixture is described along with studies on the effect that ammonia concentration and a TFA catalyst have on the product ratio. Compound 19 was converted into the 5-carboxamide and 5-thioamide derivatives of 19.
• An Efficient Synthesis of 2-Nitropyrrole-3,4-dicarboxamide
  作者：Michael T. Migawa、Leroy B. Townsend

  DOI：10.1080/00397919908086015

  日期：1999.11

  Abstract The synthesis of N-1-substituted 2-nitropyrrole-3,4-dicarboxamides (4–5, 7–9) was accomplished from diethyl 2-nitropyrrole-3,4-dicarboxylate (2). 2-nitro-pyrrole-3,4-dicarboxamide (1) was prepared by deprotection of 2-nitro-1-[2-(2-pyridyl)ethyl]pyrrole-3,4-dicarboxamide (9). Compound 9 was obtained by two different methods.

  摘要 N-1-取代的 2-硝基吡咯-3,4-二甲酰胺 (4-5, 7-9) 的合成是由 2-硝基吡咯-3,4-二甲酸二乙酯 (2) 合成的。2-硝基-吡咯-3,4-二甲酰胺(1)通过2-硝基-1-[2-(2-吡啶基)乙基]吡咯-3,4-二甲酰胺(9)的脱保护制备。化合物9是通过两种不同的方法获得的。