4-(2-氧代-3H-苯并咪唑-1-基)丁酸乙酯 | 116199-86-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 4-(2-氧代-3H-苯并咪唑-1-基)丁酸乙酯
• 英文名称: ethyl 2,3-dihydro-2-oxo-1H-benzimidazol-1-butanoate
• 英文别名: 1H-Benzimidazole-1-butanoic acid, 2,3-dihydro-2-oxo-, ethyl ester；ethyl 4-(2-oxo-3H-benzimidazol-1-yl)butanoate
• CAS: 116199-86-1
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: MLFOVEYKMYRRRN-UHFFFAOYSA-N

物化性质

• 密度：
  1.186±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：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-氧代-3H-苯并咪唑-1-基)丁酸乙酯 在 盐酸 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 4-(1,2-dihydro-2-oxobenzo[d]imidazole-3-yl)butanoic acid
  参考文献：
  名称：

  制备2，3-二氢-2-氧-1H-苯并咪唑-1-丁酸的方法

  摘要：

  本发明涉及制备2，3‑二氢‑2‑氧‑1H‑苯并咪唑‑1‑丁酸的方法，将1,3‑二氢‑1‑(1‑甲基乙烯基)‑2H‑苯并咪唑‑2‑酮在有机溶剂中，在缚酸剂的作用下于100‑120℃脱水，完毕后加入4‑溴丁酸乙酯反应，反应结束后将反应液冷到70‑90℃，加入预热到40‑60℃的水搅拌适时分相；有机相加碱于45‑80℃，150‑200mbar环境下进行皂化反应，皂化反应结束后于40‑60℃缓慢加入盐酸，然后在90‑110℃反应2‑4小时，冷却过滤，滤饼水洗，于50‑70℃，100‑180mbar下干燥至恒重。用碳酸钾代替氢化钠,根本上消除了传统工艺安全隐患大,三废污染严重等问题,而且一锅炒使得生产工艺更简便,并使得生产成本降低；同时本发明操作简便安全工艺条件合理,反应收率高,具有较高的实施价值。

  公开号：

  CN113200922A
• 作为产物：
  描述：

  3-异丙烯基-2-氧代- 在 硫酸 作用下， 以 乙醇 、 水 为溶剂， 生成 4-(2-氧代-3H-苯并咪唑-1-基)丁酸乙酯
  参考文献：
  名称：

  Novel

  摘要：

  化合物的名称为6-氨基-7-羟基-4,5,6,7-四氢咪唑[4,5,l-j-k][1]-苯并氮杂环-2-(1H)-酮衍生物，化学式为##STR1##其中R选自氢，1至8个碳原子的烷基，可选用羟基，6至10个碳原子的芳基和芳氧基，3至7个碳原子的环烷基，可选用杂原子打断，可选用1至4个碳原子的烷基取代，并且波浪线表示7-OH和6-氨基具有反式构型，它们的非毒性，药学上可接受的酸盐具有显著的抗高血压和低血压活性以及血管扩张活性，其制备方法。

  公开号：

  US04585770A1

文献信息

• Novel
  申请人：Roussel Uclaf

  公开号：US04585770A1

  公开（公告）日：1986-04-29

  Novel 6-amino-7-hydroxy-4,5,6,7-tetrahydro-imidazo[4,5,l-j-k][1]-benzazepin-2-(1 H)-one derivatives of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms optionally substituted with a hydroxyl, aryl and aryloxy of 6 to 10 carbon atoms, cycloalkyl of 3 to 7 carbon atoms optionally interrupted with a heteroatom optionally substituted with alkyl of 1 to 4 carbon atoms and the wavy lines indicates that the 7-OH and 6-amino have the trans configuration and their non-toxic, pharmaceutically acceptable acid addition salts having remarkable anti-hypertensive and hypotensive activity and vasodilatatory activity and their preparation.

  化合物的名称为6-氨基-7-羟基-4,5,6,7-四氢咪唑[4,5,l-j-k][1]-苯并氮杂环-2-(1H)-酮衍生物，化学式为##STR1##其中R选自氢，1至8个碳原子的烷基，可选用羟基，6至10个碳原子的芳基和芳氧基，3至7个碳原子的环烷基，可选用杂原子打断，可选用1至4个碳原子的烷基取代，并且波浪线表示7-OH和6-氨基具有反式构型，它们的非毒性，药学上可接受的酸盐具有显著的抗高血压和低血压活性以及血管扩张活性，其制备方法。
• 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.
• US4585770A
  申请人：——

  公开号：US4585770A

  公开（公告）日：1986-04-29
• 制备2，3-二氢-2-氧-1H-苯并咪唑-1-丁酸的方法
  申请人：上海红象生物医药科技有限公司

  公开号：CN113200922A

  公开（公告）日：2021-08-03

  本发明涉及制备2，3‑二氢‑2‑氧‑1H‑苯并咪唑‑1‑丁酸的方法，将1,3‑二氢‑1‑(1‑甲基乙烯基)‑2H‑苯并咪唑‑2‑酮在有机溶剂中，在缚酸剂的作用下于100‑120℃脱水，完毕后加入4‑溴丁酸乙酯反应，反应结束后将反应液冷到70‑90℃，加入预热到40‑60℃的水搅拌适时分相；有机相加碱于45‑80℃，150‑200mbar环境下进行皂化反应，皂化反应结束后于40‑60℃缓慢加入盐酸，然后在90‑110℃反应2‑4小时，冷却过滤，滤饼水洗，于50‑70℃，100‑180mbar下干燥至恒重。用碳酸钾代替氢化钠,根本上消除了传统工艺安全隐患大,三废污染严重等问题,而且一锅炒使得生产工艺更简便,并使得生产成本降低；同时本发明操作简便安全工艺条件合理,反应收率高,具有较高的实施价值。