2-(1H-咪唑-1-基)琥珀酸二乙酯 | 141264-13-3

• 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
• 中文名称: 2-(1H-咪唑-1-基)琥珀酸二乙酯
• 英文名称: Diethyl 2-imidazol-1-ylbutanedioate
• CAS: 141264-13-3
• 化学式: C₁₁H₁₆N₂O₄
• 分子量: 240.259
• InChiKey: KIWTYXNPDAOSOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  70.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(1H-咪唑-1-基)琥珀酸二乙酯 在 臭氧 作用下， 以 甲醇 为溶剂， 以72%的产率得到N-<1,2-di(ethoxycarbonyl)ethyl>-N-formylformamide
  参考文献：
  名称：

  Ozonolysis of 1-Substituted Imidazoles

  摘要：

  1-Substituted imidazoles was ozonolyzed cleanly without any complicated procedures into the corresponding N-acylamides, which were regarded to be much useful derivatives of either amines or acyl compounds.

  DOI：

  10.3987/com-91-s67
• 作为产物：
  描述：

  咪唑 、 富马酸二乙酯 反应 24.0h， 生成 2-(1H-咪唑-1-基)琥珀酸二乙酯
  参考文献：
  名称：

  外消旋咪唑-1基琥珀酸衍生物的多态性。通过磁共振光谱成像 (MRSI) 检测细胞外 pH 值的合适探针。

  摘要：

  通过在不同溶剂中结晶来研究外消旋咪唑-1基琥珀酸衍生物的多态性，这是一系列以前用作核磁共振光谱的细胞外 pH 探针的化合物。单酯，(±)-3-(乙氧基羰基)-2-(咪唑-1-基)丙酸，分别在无水乙醇(I型)或水(II型)中重结晶时显示两种不同的多晶型物。这两种形式已通过光学显微镜、粉末 X 射线衍射分析和热重分析进行表征。多晶型物 I 和 II 也可以通过固态 CP-MAS C NMR 光谱进行区分。

  DOI：

  10.3998/ark.5550190.0012.314

文献信息

• Synthesis and Regioselective Hydrolysis of 2-(Imidazol-1-yl)succinic Esters
  作者：Paula Zaderenko、M. Soledad Gil、Paloma Ballesteros、Sebastian Cerdan

  DOI：10.1021/jo00100a030

  日期：1994.10

  (+/-)-2-Imidazol-1-ylsuccinic esters were synthesized by thermal addition of imidazole to either fumaric or maleic esters. Acceleration of the reaction was achieved, in some cases, using microwave heating. These esters underwent an easy regioselective hydrolysis, under neutral conditions, to give the corresponding half-esters: (+/-)-3-(alkoxycarbonyl)-2-imidazol-1-ylpropionic acids, through either BAC(3) or BAL(1) mechanisms. Kinetic studies in H2O and D2O as well as O-18 and O-17 labeling experiments supported the proposed mechanism. The results of these hydrolyses, which depended on the nature of the alcohol moiety, were compared with those obtained with some imidazol-1-ylacetate analogues or with (+/-)-2-pyrazol-1-yl- and benzimidazol-1-ylsuccinic esters. In general, imidazolylsuccinic esters hydrolyzed faster than the homologous derivatives from pyrazole or benzimidazole.

  (±)-2-咪唑-1-基琥珀酸酯是通过将咪唑与富马酸酯或马来酸酯在热条件下进行加成反应而合成的。在某些情况下，通过微波加热可以加速反应进程。这些酯在中性条件下经历一种简单的区域选择性水解，生成相应的半酯：(±)-3-(烷氧基羰基)-2-咪唑-1-基丙二酸，其水解机制可能涉及BAC(3)或BAL(1)路径。在H2O和D2O中的动力学研究，以及O-18和O-17的标记实验结果，均支持了所提出的水解机制。这些水解产物的性质依赖于醇基的类型，与一些咪唑-1-基丙二酸酯类似物，或与(±)-2-吡唑-1-基和苯并咪唑-1-基琥珀酸酯的水解结果进行比较。总体而言，咪唑基琥珀酸酯的水解速度比来自吡唑或苯并咪唑的同类衍生物更快。
• Synthesis of multicarboxylic acid appended imidazolium ionic liquids and their application in palladium-catalyzed selective oxidation of styrene
  作者：Xuehui Li、Weiguo Geng、Jixiang Zhou、Wei Luo、Furong Wang、Lefu Wang、Shik Chi Tsang

  DOI：10.1039/b702573d

  日期：——

  A series of multicarboxylic acid appended imidazolium ionic liquids (McaILs) with chloride [Cl]– or bromide [Br]– as anions have been synthesized and characterized. Deprotonation of these ionic acids gives the corresponding zwitterions. Re-protonation of the zwitterions with strong Brønsted acids gives a series of new ionic acid-adducts, many of which remained as room-temperature ionic liquids. A new catalytic system, McaIL/PdCl2 for the selective catalytic oxidation of styrene to acetophenone with hydrogen peroxide as an oxidant has been attempted. In the presence of McaILs, it is found that the quantity of palladium chloride PdCl2 used can be greatly reduced while the activity (TOF) and selectivity towards acetophenone are enhanced sharply. It is also shown that the catalytic properties of this system could be finely tuned through the molecular design of the McaILs. The best TOF value obtained so far is 146 h–1 with 100% conversion of styrene at 93% selectivity to acetophenone. In addition, the catalytic activity has been maintained for at least ten catalytic cycles.

  我们合成了一系列以氯[Cl]-或溴[Br]-为阴离子的多羧酸附加咪唑离子液体（McaILs），并对其进行了表征。对这些离子酸进行去质子化可得到相应的齐聚物。这些齐聚物与强勃氏酸发生再质子化反应，产生了一系列新的离子酸加成物，其中许多仍然是室温离子液体。我们尝试了一种新的催化体系--McaIL/PdCl2，用于以过氧化氢为氧化剂将苯乙烯选择性催化氧化为苯乙酮。研究发现，在 McaIL 的存在下，氯化钯 PdCl2 的用量可以大大减少，而活性（TOF）和对苯乙酮的选择性却大幅提高。研究还表明，该系统的催化特性可以通过对 McaILs 的分子设计进行微调。目前获得的最佳 TOF 值为 146 h-1，苯乙烯的转化率为 100%，对苯乙酮的选择性为 93%。此外，这种催化活性还能保持至少十次催化循环。
• Ozonolysis of 1-Substituted Imidazoles
  作者：Choji Kashima、Kaori Harada、Akira Hosomi

  DOI：10.3987/com-91-s67

  日期：——

  1-Substituted imidazoles was ozonolyzed cleanly without any complicated procedures into the corresponding N-acylamides, which were regarded to be much useful derivatives of either amines or acyl compounds.
• Polymorphism of racemic imidazol-1yl succinic acid derivatives. Suitable probes for extracellular pH by magnetic resonance spectroscopic imaging (MRSI).
  作者：Paloma Ballesteros、Carmen Ubide-Barreda、Mª Luisa Rojas、Pedro José Martínez de Paz、Valeria Righi

  DOI：10.3998/ark.5550190.0012.314

  日期：——

  The polymorphism of racemic imidazol-1ylsuccinic acid derivatives, a series of compounds previously used as extracellular pH probes for NMR spectroscopy, is investigated by crystallization in different solvents. The mono-ester, (±)-3-(ethoxycarbonyl)-2-(imidazol-1-yl) propionic acid, shows two different polymorphs when recrystallized in absolute ethanol (Form I) or water (Form II), respectively. These

  通过在不同溶剂中结晶来研究外消旋咪唑-1基琥珀酸衍生物的多态性，这是一系列以前用作核磁共振光谱的细胞外 pH 探针的化合物。单酯，(±)-3-(乙氧基羰基)-2-(咪唑-1-基)丙酸，分别在无水乙醇(I型)或水(II型)中重结晶时显示两种不同的多晶型物。这两种形式已通过光学显微镜、粉末 X 射线衍射分析和热重分析进行表征。多晶型物 I 和 II 也可以通过固态 CP-MAS C NMR 光谱进行区分。