1-N-hexylbenzimidazol-2-one | 282088-69-1

• 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: 1-N-hexylbenzimidazol-2-one
• 英文别名: 3-hexyl-1H-benzimidazol-2-one
• CAS: 282088-69-1
• 化学式: C₁₃H₁₈N₂O
• mdl: MFCD03669584
• 分子量: 218.299
• InChiKey: IDTLKMNKJYQAMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5,6-anhydro-1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose 、 1-N-hexylbenzimidazol-2-one 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以96%的产率得到1-N-(6-deoxy-1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranos-6-yl)-3-N-hexylbenzimidazol-2-one
  参考文献：
  名称：

  Towards the synthesis of new benzimidazolone derivatives with surfactant properties

  摘要：

  New water-soluble benzimidazolone derivatives were synthesized. In the first approach, di-N-glycosyl and mono-N-alkyl-N-glycosyl compounds were obtained by grafting C-6-activated glycosides onto benzimidazolone. In the second approach, benzimidazolone derivatives bearing a glucosyl unit were synthesized using an efficient glycosylation method. Every compound structure was confirmed by means of NMR spectroscopy and elemental analysis. The preliminary surfactant properties of some compounds were evaluated. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.11.028
• 作为产物：
  描述：

  1-N-hexyl-3-N-isopropenylbenzimidazol-2-one 在 硫酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以83%的产率得到1-N-hexylbenzimidazol-2-one
  参考文献：
  名称：

  Towards the synthesis of new benzimidazolone derivatives with surfactant properties

  摘要：

  New water-soluble benzimidazolone derivatives were synthesized. In the first approach, di-N-glycosyl and mono-N-alkyl-N-glycosyl compounds were obtained by grafting C-6-activated glycosides onto benzimidazolone. In the second approach, benzimidazolone derivatives bearing a glucosyl unit were synthesized using an efficient glycosylation method. Every compound structure was confirmed by means of NMR spectroscopy and elemental analysis. The preliminary surfactant properties of some compounds were evaluated. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.11.028

文献信息

• [EN] BENZIMIDAZOLONE DERIVATIVES AS 5-HT1A AND 5-HT2 ANTAGONISTS
  申请人：BOEHRINGER INGELHEIM ITALIA S.P.A.

  公开号：WO1993003016A1

  公开（公告）日：1993-02-18

  (EN) Pharmacologically active benzimidazolone derivatives as 5-HT1A and 5-HT2 receptors, useful in the treatment of CNS disorders of formula (I), wherein R1 and R2 may be at the same time or not a hydrogen atom, halogen, trifluoromethyl, C1-6 alkyl, C1-6 alkoxy, C1-6 alkylthio, C1-6 acyl, carboxyl, C1-6 alkoxy- carbonyl, hydroxy, nitro, amino optionally C1-4 alkyl N-mono or di-substituted, C1-6 acylamino, C1-6 alkoxycarbonylamino, carbamoyl optionally C1-4 alkyl N-mono or di-substituted, cyano, C1-6 alkylsulphinyl, C1-6 alkylsulphonyl, amino sulphonyl optionally C1-4 alkyl N-mono or di-substituted, C1-4 alkyl N-mono or di-substituted aminosulphonylamino, aminosulphonylamino; R3 is hydrogen, C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl; A is -CO- or -CONH- or it is absent; B is a straight or branched, saturated or unsaturated C2-6 alkyl; m and n are both independently an integer from 1 to 3; R4 is an aryl, aralkyl, a heteroaryl, or heteroaralkyl group, each group being optionally substituted by one or more substituents selected from halogen, trifluoromethyl, cyano, C1-3 alkoxy, C1-4 alkyl and acid addition salts thereof. The process for the preparation of the compounds of formula (I) as well as pharmaceutical compositions containing them are also described.(FR) Dérivés pharmacologiquement actifs de benzimidazolone servant de récepteurs de 5-HT1A et de 5-HT2 et utiles dans le traitement des troubles du système nerveux central. Ils répondent à la formule (I), dans laquelle R1 et R2 sont identiques ou différents et représentent un atome d'hydrogène, halogène, trifluorométhyle, alkyle C1-6, alcoxy C1-6, alkylthio C1-6, acyle C1-6, carboxyle, alcoxy C1-6 -carbonyle, hydroxy, nitro, amino éventuellement N-monosubstitué ou disubstitué par alkyle C1-4, acylamino C1-6, alcoxycarbonylamino C1-6, carbamoyle éventuellement N-monosubstitué ou disubstitué par alkyle C1-4, alkylsufinyle C1-6, alkylsulfonyle C1-6, aminosulfonyle éventuellement N-mono ou disubstitué par alkyle C1-4, aminosulfonylamino N-mono ou disubstitué par alkyle C1-4, ou aminosulfonylamino; R3 représente hydrogène, alkyle C1-6, alcényle C2-6, ou alcynyle C2-6; A représente -CO- ou -CONH- ou est absent; B représente alkyle C2-6 linéaire ou ramifié et saturé ou insaturé; m et n, indépendamment l'un de l'autre, représentent un nombre entier compris entre 1 et 3; R4 représente un groupe aryle, aralkyle, hétéroaryle ou hétéroaralkyle, chaque groupe étant éventuellement substitué par un ou plusieurs substituant sélectionnés parmi halogène, trifluorométhyle, cyano, alcoxy C1-3, alkyl C1-4, et leurs sels d'addition d'acide. On a également prévu un procédé de préparation des composés de la formule (I), ainsi que des compositions pharmaceutiques les contenant.

  具有药理活性的苯并咪唑酮衍生物作为5-HT1A和5-HT2受体，在治疗公式（I）中的中枢神经系统疾病中有用，其中R1和R2可以同时也可以不是氢原子，卤素，三氟甲基，C1-6烷基，C1-6烷氧基，C1-6烷硫基，C1-6酰基，羧基，C1-6烷氧基-羰基，羟基，硝基，氨基可选C1-4烷基N-单或双取代，C1-6酰基氨基，C1-6烷氧羰基氨基，氨基甲酰基可选C1-4烷基N-单或双取代，氰基，C1-6烷基磺酰基，C1-6烷基磺酰基，氨基磺酰基可选C1-4烷基N-单或双取代，C1-4烷基N-单或双取代氨基磺酰氨基，氨基磺酰氨基；R3是氢，C1-6烷基，C2-6烯基或C2-6炔基；A是-CO-或-CONH-或不存在；B是直链或支链，饱和或不饱和的C2-6烷基；m和n都是独立的1到3的整数；R4是芳基，芳基烷基，杂芳基或杂芳基烷基基团，每个基团都可以选择地被一个或多个取代基取代，所述取代基被选择自卤素，三氟甲基，氰基，C1-3烷氧基，C1-4烷基和它们的酸加成盐。还描述了制备公式（I）化合物的过程以及含有它们的制药组合物。
• Benzimidazolone derivatives
  申请人：Boehringer Ingelheim Italia S.p.A.

  公开号：US05576318A1

  公开（公告）日：1996-11-19

  Pharmacologically active benzimidazolone derivatives as 5-HT.sub.1A and 5-HT.sub.2 receptors, useful in the treatment of CNS disorders, of formula: ##STR1## wherein the substituents are defined herein.

  具有药理活性的苯并咪唑酮衍生物作为5-HT.sub.1A和5-HT.sub.2受体，用于治疗中枢神经系统疾病，其化学式如下：##STR1## 其中取代基在此定义。
• Benzimidazolone derivatives as 5-HT1A and 5-HT2 antagonists
  申请人：BOEHRINGER INGELHEIM ITALIA S.p.A.

  公开号：EP0526434B1

  公开（公告）日：2000-04-19
• Use of polymer supported thiophenol for the synthesis and purification of a benzimidazol-2-one library
  作者：Monika Ermann、Nadja M Simkovsky、Stanley M Roberts、David M Parry、Andy D Baxter、John G Montana

  DOI：10.1016/s0040-4039(00)00185-4

  日期：2000.4

  An efficient solution phase synthesis of substituted benzimidazol-2-ones is described. Polymer-supported thiophenol is used to remove excess alkylating agents. A library of 24 mono- and di-substituted benzimidazol-2-ones has been prepared in 60-99% yield and 65-99% purity. (C) 2000 Elsevier Science Ltd. All rights reserved.
• US5576318A
  申请人：——

  公开号：US5576318A

  公开（公告）日：1996-11-19