2H-苯并咪唑-2-酮 | 63388-01-2

• 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: 2H-苯并咪唑-2-酮
• 中文别名: 1-(2-氯乙基)-2,3-二氢苯并咪唑-2-酮
• 英文名称: 1-(2-hydroxy-ethyl)-1,3-dihydro-benzoimidazol-2-one
• 英文别名: 1,3-dihydro-1-(2-hydroxyethyl)-2H-benzimidazol-2-one；1-(2-hydroxyethyl)benzimidazolone；2-Oxo-1-(2-hydroxy-ethyl)-benzimidazolin；1-(2-Hydroxyethyl)-1H-benzo[d]imidazol-2(3H)-one；3-(2-hydroxyethyl)-1H-benzimidazol-2-one
• CAS: 63388-01-2
• 化学式: C₉H₁₀N₂O₂
• 分子量: 178.191
• InChiKey: ZONXBNQBUCKCLU-UHFFFAOYSA-N

物化性质

• 熔点：
  140-142°C
• 密度：
  1.298±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于乙腈（少许）、DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  对氟碘苯 、 2H-苯并咪唑-2-酮 在 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 、 水 为溶剂， 生成 1-(4-fluorophenyl)-3-(2-hydroxyethyl)-2(3H)-benzimidazolone
  参考文献：
  名称：

  Fused benzo compounds containing a nitrogen heterocycle for the

  摘要：

  提供了式I的融合苯并化合物，其中A是一个2到6个成员的碳氢化合物间隔基团，B是从组（a）中选择的极性二价基团；U是C、N或CH；X是一个二价的3-4个成员的链，可选地包括一个或多个杂原子；R.sup.1是一个脂肪烃基、芳基烷基或二苯基烷基；R.sup.2和R.sup.3是氢或烷基，或者一起形成一个乙烯或丙烯桥；R.sup.4、R.sup.5和R.sup.6是氢或取代基；R.sup.7和R.sup.8是氢或取代基，包括--COOR.sup.9和--CONR.sup.10 R.sup.11；是用于治疗中枢神经系统疾病的5-HT.sub.1A受体配体。还提供了包含这些化合物的药物组合物以及它们用于制备药物制剂的用途。

  公开号：

  US05753661A1
• 作为产物：
  描述：

  2-羟基苯并咪唑 在 sodium hydroxide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.5h， 生成 2H-苯并咪唑-2-酮
  参考文献：
  名称：

  Regiospecific Functionalization of 1,3-Dihydro-2H-benzimidazol-2-one and Structurally Related Cyclic Urea Derivatives

  摘要：

  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.

  DOI：

  10.1021/jo00111a014

文献信息

• 1-Benzazolylalkyl-4-substituted-piperidines
  申请人：Janssen Pharmaceutica N.V.

  公开号：US04035369A1

  公开（公告）日：1977-07-12

  Compounds of the class of 1-(benzazolyalkyl)piperidine derivatives, useful as neuroleptic agents.

  苯并咪唑烷基哌啶衍生物类化合物，可用作抗精神病药物。
• Fused benzo compounds for the treatment of central nervous system
  申请人：H. Lundbeck A/S

  公开号：US06140331A1

  公开（公告）日：2000-10-31

  ##STR1## Fused benzo compounds of formula (I), wherein A is a 2 to 6 membered hydrocarbon spacer group, B is a polar divalent group selected from SO, SO.sub.2, and a group (a); U is C, N or CH; X is a divalent 3-4 membered chain optionally comprising one or more heteroatoms; R.sup.1 is an aliphatic hydrocarbon group, arylalkyl or diphenylalkyl; R.sup.2 and R.sup.3 are hydrogen or alkyl or together form an ethylene or propylene bridge; R.sup.4, R.sup.5 and R.sup.6 are hydrogen or substituents; R.sup.7 and R.sup.8 are hydrogen or substituents including, a group --COOR.sup.9 and a group --CONR.sup.10 R.sup.11 ; are 5-HT.sub.1A receptor ligands useful in the treatment of CNS disorders. Pharmaceutical compositions comprising the compounds and their use for the manufacture of a pharmaceutical preparation are also disclosed.

  式（I）的熔合苯化合物，其中A是2-6成员的烃间隔基，B是极性二价基团，选自SO、SO.sub.2和一个基团（a）；U是C、N或CH；X是二价的3-4成员链，可包含一个或多个杂原子；R.sup.1是脂肪烃基，芳基烷基或二苯基烷基；R.sup.2和R.sup.3是氢或烷基，或共同形成乙烯或丙烯桥；R.sup.4、R.sup.5和R.sup.6是氢或取代基；R.sup.7和R.sup.8是氢或取代基，包括一个羧酸酯基团--COOR.sup.9和一个羧酰氨基团--CONR.sup.10R.sup.11；是5-HT.sub.1A受体配体，对CNS疾病的治疗有用。还公开了包含该化合物的药物组合物及其用于制造药物制剂的用途。
• FUSED BENZO COMPOUNDS
  申请人：H. LUNDBECK A/S

  公开号：EP0673375B1

  公开（公告）日：1999-02-24
• US4035369A
  申请人：——

  公开号：US4035369A

  公开（公告）日：1977-07-12
• US5753661A
  申请人：——

  公开号：US5753661A

  公开（公告）日：1998-05-19