diethyl 2-oxo-1H benzo[d]imidazole-1,3(2H)-dicarboxylate | 161468-57-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: diethyl 2-oxo-1H benzo[d]imidazole-1,3(2H)-dicarboxylate
• 英文别名: 2-oxo-benzoimidazole-1,3-dicarboxylic acid diethyl ester；diethyl 2-oxobenzimidazole-1,3-dicarboxylate；diethyl 2-oxo-1H-1,3-benzimidazole-1,3(2H)-dicarboxylate
• CAS: 161468-57-1
• 化学式: C₁₃H₁₄N₂O₅
• 分子量: 278.265
• InChiKey: IWMJHUHILXJBEO-UHFFFAOYSA-N

物化性质

• 熔点：
  123～126℃
• 沸点：
  384.4±25.0 °C(Predicted)
• 密度：
  1.354±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 2-oxo-1H benzo[d]imidazole-1,3(2H)-dicarboxylate 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 2-羟基苯并咪唑
  参考文献：
  名称：

  Synthesis of Benzimidazolones, Benzooxazolones, 2-amino-benzothiazoles from Ethyl Cyanoformate and o-phenylene Diamines, o-aminophenols, oaminothiophenols Promoted by Lithium Bromide

  摘要：

  研究了溴化锂介导的1-氨基-2-杂芳基底物与氰基甲酸乙酯的缩合反应，以获得多样的烷基氨基甲酸酯保护的苯并杂氮卓酮。这一前所未有的反应可用于以良好产率制备不同的氮卓酮，如2-苯并咪唑酮、2-苯并噁唑酮和2-氨基噻唑。

  DOI：

  10.2174/157017811796064449
• 作为产物：
  描述：

  diethyl 2-chloro-3a,7a-dihydro-2H-benzimidazole-1,3-dicarboxylate 在 potassium permanganate 、 18-冠醚-6 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以70%的产率得到diethyl 2-oxo-1H benzo[d]imidazole-1,3(2H)-dicarboxylate
  参考文献：
  名称：

  苯并咪唑和酰氯的加合物的α-酰胺烷基化反应和氧化

  摘要：

  摘要 苯并咪唑和酰氯的加合物 4 成功用作亲电试剂，用于酮的分子间 α-酰胺烷基化反应合成 2-(2-氧代烷基)-1,3-二酰基-2,3-二氢苯并咪唑 6 并用 KMnO4 氧化至 1,3-二酰基-2,3-二氢苯并咪唑-2-酮 7.

  DOI：

  10.1080/00397919808007016

文献信息

• Structural analysis of intramolecular 1,5-type O⋯O and S⋯O interactions in diethyl 2-oxo and diethyl 2-thioxo-1H benzo[d]imidazole-1,3(2H)-dicarboxylate: Experimental and theoretical study
  作者：Fernando Obledo-Benicio、Nancy Evelyn Magaña-Vergara、Kayim Pineda-Urbina、David J. Pérez、Maria M. Romero-Chávez、Juan Pablo Mojica-Sánchez、Omar Ramos-Rodríguez、Ángel Ramos-Organillo

  DOI：10.1016/j.molstruc.2020.127929

  日期：2020.6

  a zig-zag arrangement due to the intermolecular aromatic interaction C–H⋯O C. A computational conformational study was made to support and explain the resulting structures stabilities. Furthermore, a QTAIM analysis was performed to study the nature of the intramolecular 1,5-type O⋯O and S⋯O interactions.

  摘要 合成了2-羟基和2-巯基苯并咪唑衍生的4种化合物，并通过红外光谱、核磁共振和元素分析对其进行了表征。得到的两种化合物——2-氧代-1H 苯并[d]咪唑-1,3(2H)-二羧酸二乙酯和2-硫代-1H 苯并[d]咪唑-1,3(2H)-二羧酸二乙酯——结晶并通过 X 射线衍射分析。前者呈现双齿氢键的分子间相互作用和通过 C–H⋯OC 形成 R 2 2 (10) 环，导致堆叠排列，而后者由于分子间芳香相互作用 C– 而呈锯齿形排列H⋯O C. 进行了计算构象研究以支持和解释由此产生的结构稳定性。此外，还进行了 QTAIM 分析以研究分子内 1、
• SUBSTITUTED BENZIMIDAZOLONE DERIVATIVES, MEDICAMENTS COMPRISING THEM AND THEIR USE
  申请人：Arndt Torsten

  公开号：US20120172335A1

  公开（公告）日：2012-07-05

  The present invention relates to novel benzimidazolone derivatives of the general formula (I) in which the substituents R 1 , R 2 , R 3 , A 1 , A 2 , and B are as defined in claim 1 , medicaments comprising these, and the use thereof for the prophylaxis and/or treatment of vasopressin-dependent diseases.

  本发明涉及一种新型苯并咪唑酮衍生物，其通式为（I），其中取代基R1、R2、R3、A1、A2和B如权利要求书所定义，包括这些衍生物的药物以及它们在抗利尿激素依赖性疾病的预防和/或治疗中的应用。
• Substituted benzimidazolone derivatives, medicaments comprising them and their use
  申请人：Abbott GmbH & Co. HG

  公开号：US08119676B2

  公开（公告）日：2012-02-21

  The present invention relates to novel benzimidazolone derivatives of the general formula (I) in which the substituents R1, R2, R3, A1, A2, and B are as defined in claim 1, medicaments comprising these, and the use thereof for the prophylaxis and/or treatment of vasopressin-dependent diseases.

  本发明涉及一种新型苯并咪唑酮衍生物，其一般式为(I)，其中取代基R1、R2、R3、A1、A2和B的定义如权利要求书1所述，包括这些衍生物的药物，以及用于预防和/或治疗利尿激素依赖性疾病的使用。
• WO2008/25736
  申请人：——

  公开号：——

  公开（公告）日：——
• Regiospecific Functionalization of 1,3-Dihydro-2H-benzimidazol-2-one and Structurally Related Cyclic Urea Derivatives
  作者：Nicholas A. Meanwell、Sing Yuen Sit、Jinnian Gao、Henry S. Wong、Qi Gao、Denis R. St. Laurent、Neelakantan Balasubramanian

  DOI：10.1021/jo00111a014

  日期：1995.3

  Methods for selectively protecting one of the degenerate nitrogen atoms of the cyclic urea derivatives 1,3-dihydro-2H-benzimidazol-2-one (6a), 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (11), 1,3-dihydro-2H-imidazo[4,5-b]quinolin-2-ones (20), 1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one (22), and 1,3-dihydro-4-phenyl-2H-imidazol-2-one (27) were developed. Heating these cyclic ureas with ethyl 2-pyridyl carbonate in the presence of a base in CH3CN at reflux or DMF at 100 degrees C cleanly provided the monoethoxycarbonyl derivatives 7a, 12, 21, 23, and 28, respectively. Alternatively, treatment of 6a with an excess of diethyl pyrocarbonate or di-tert-butyl dicarbonate afforded the bis-alkoxycarbonyl derivatives 8a and 8b, respectively, which underwent disproportionation to 7a and 7b upon heating with 1 mol equiv of 6a and K2CO3 in CH3CN at reflux. The regiochemistry of the introduction of alkoxycarbonyl groups to benzimidazol-2-one derivatives was not significantly influenced by an electron-withdrawing (CF3, 6b) or an electron-donating (OCH3, 6c) substituent at C-5 of the heterocyclic ring. However, the reaction was found to be sensitive to steric factors since a chlorine substituent ortho to one of the urea N atoms (6e) completely directed the alkoxycarbonyl moiety to the less sterically encumbered N atom, affording a single product (7f, 7g). Alkylation of 7a-g proceeded efficiently to provide products 10a-10ag after removal of the protecting group. Halogenation of monoprotected benzimidazol-2-one 7a occurred regiospecifically to give the monohalo derivatives 7h, 7i, and 7k, the identity of which were readily established from the characteristic chemical shift and spin coupling pattern in their 1H NMR spectra. A protecting group interchange strategy that took advantage of the distinctive chemical reactivities of the EtO(2)C and t-BuO(2)C protecting groups toward isopropylamine was developed that provided access to the isomerically substituted series of monohalo, mono-N-alkylated benzimidazol-2-ones 71 and 7m. The efficient derivatization of the unprotected N atom of these monoprotected cyclic urea derivatives was accomplished by treating with activated and unactivated halides in the. presence of K2CO3 or exposure to alcohols under Mitsunobu conditions. In several cases, mixtures of O- and N-alkylated products were produced which were readily separated by chromatography. Alkylation of 7h with activated halides, using K2CO3 in CH3CN at reflux, occurred without protecting group equilibration; however, a mixture of isomeric alkylated products was obtained when 7h was heated at 110 degrees C in DMF with cyclohexylmethyl bromide in the presence of K2CO3 as the base. Derivatization of 7h under Mitsunobu reaction conditions proceeded with retention of the topological substituent relationships. Subsequent removal of the alkoxycarbonyl moiety afforded monoalkylated cyclic urea derivatives.