1-dimethylsulfamoyl-4,5,6,7-tetrahydro-1H-benzimidazole | 558443-63-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-dimethylsulfamoyl-4,5,6,7-tetrahydro-1H-benzimidazole
• 英文别名: 4,5,6,7-tetrahydro-benzoimidazole-1-sulfonic acid dimethylamide；N,N-Dimethyl-4,5,6,7-tetrahydro-1H-benzimidazole-1-sulfonamide；N,N-dimethyl-4,5,6,7-tetrahydrobenzimidazole-1-sulfonamide
• CAS: 558443-63-3
• 化学式: C₉H₁₅N₃O₂S
• 分子量: 229.303
• InChiKey: CWDOGKHFSGFUQC-UHFFFAOYSA-N

物化性质

• 沸点：
  396.6±45.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-dimethylsulfamoyl-4,5,6,7-tetrahydro-1H-benzimidazole 在 sodium tetrahydroborate 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 2-amino-N,N-dimethyl-4,5,6,7-tetrahydrobenzimidazole-1-sulfonamide
  参考文献：
  名称：

  Oxidative reactions of tetrahydrobenzimidazole derivatives with N-sulfonyloxaziridines

  摘要：

  An investigation of the utility of N-sulfonyloxaziridines to effect the oxidative rearrangement of tetrahydrobenzimidazoles to spiro fused 5-imidazolones is reported. In addition to the anticipated rearrangement manifold, it was found that 2-amino substituted derivatives afford products resulting from rearrangement, or alternatively from addition of methanol or water depending on the nature of the N-substituents and reaction conditions. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.088
• 作为产物：
  描述：

  4,5,6,7-四氢-1H-苯并咪唑 、 二甲胺基磺酰氯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以65%的产率得到1-dimethylsulfamoyl-4,5,6,7-tetrahydro-1H-benzimidazole
  参考文献：
  名称：

  Oxidative Rearrangement of Imidazoles with Dimethyldioxirane

  摘要：

  Tetrahydrobenzimidazoles, on treatment with dimethyldioxirane, rearrange to provide 5-imidazolones exclusively. These rearrangements proceed with a broad range of substrates and with good to excellent levels of diastereoselectivity.

  DOI：

  10.1021/ol036403w

文献信息

• Chemokine receptor binding heterocyclic compounds with enhanced efficacy
  申请人：——

  公开号：US20030220341A1

  公开（公告）日：2003-11-27

  The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

  这项发明涉及由一个核心氮原子环绕着三个侧链基团的杂环化合物，其中三个侧链基团中的两个最好是苯并咪唑甲基和四氢喹啉基，第三个侧链基团含有N，并且可选地含有额外的环。这些化合物与趋化因子受体结合，包括CXCR4和CCR5，并且表现出对人类免疫缺陷病毒（HIV）感染靶细胞的保护作用。
• Thio acid-mediated conversion of azides to amides – Investigation of 2-azidotetrahydobenzimidazoles and derivatives
  作者：Lawton A. Seal、Olatunji S. Ojo、Delphine Gout、Carl J. Lovely

  DOI：10.1016/j.tetlet.2020.152484

  日期：2020.11

  investigation of the thio acid-azide coupling reaction to afford amides is reported employing 2-azidotetrahydrobenzimidazoles and the corresponding spiro fused 2-azidoimidazolones. The tetrahydrobenzimidazole derivatives react as expected to produce the analogous amides, whereas the imidazolones result in the formation of the thiohydantoin derivatives. The thiohydantoins appear to result from an addition elimination

  报道了使用2-叠氮基四氢苯并咪唑和相应的螺稠的2-叠氮基咪唑酮对硫氰酸-叠氮化物偶联反应提供酰胺的研究。四氢苯并咪唑衍生物按预期反应生成类似的酰胺，而咪唑酮则导致硫代乙内酰脲衍生物的形成。硫代乙内酰脲似乎是由附加消除途径引起的。
• [EN] CHEMOKINE RECEPTOR BINDING HETEROCYCLIC COMPOUNDS WITH ENHANCED EFFICACY<br/>[FR] COMPOSES HETEROCYCLIQUES A EFFICACITE ACCRUE SE FIXANT SUR LES RECEPTEURS DE LA CHIMIOKINE
  申请人：ANORMED INC

  公开号：WO2003055876A1

  公开（公告）日：2003-07-10

  The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

  本发明涉及由一个核心氮原子和三个侧链基团组成的杂环化合物，其中三个侧链基团中的两个首选为苯并咪唑甲基和四氢喹啉基，第三个侧链基团含有N并可选择性地含有其他环。这些化合物结合趋化因子受体，包括CXCR4和CCR5，并对人免疫缺陷病毒（HIV）感染靶细胞表现出保护作用。
• CHEMOKINE RECEPTOR BINDING HETEROCYCLIC COMPOUNDS WITH ENHANCED EFFICACY
  申请人：BRIDGER Gary

  公开号：US20080167341A1

  公开（公告）日：2008-07-10

  The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

  该发明涉及由一个核心氮原子和三个侧链基团组成的杂环化合物，其中三个侧链基团中有两个是苯并咪唑甲基和四氢喹啉基，第三个侧链基团含有N，并且可以含有额外的环。这些化合物结合趋化因子受体，包括CXCR4和CCR5，并且表现出对人类免疫缺陷病毒（HIV）感染靶细胞的保护效果。
• Chemokine Receptor Binding Heterocyclic Compounds With Enhanced Efficacy
  申请人：Genzyme Corporation

  公开号：US20150038509A1

  公开（公告）日：2015-02-05

  The invention relates to heterocyclic compounds consisting of a core nitrogen atom surrounded by three pendant groups, wherein two of the three pendant groups are preferably benzimidazolyl methyl and tetrahydroquinolyl, and the third pendant group contains N and optionally contains additional rings. The compounds bind to chemokine receptors, including CXCR4 and CCR5, and demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

  该发明涉及杂环化合物，其由一个核心氮原子和三个下垂基团组成，其中三个下垂基团中的两个优选为苯并咪唑甲基和四氢喹啉基，第三个下垂基团含有N，并且可以包含其他环。这些化合物结合趋化因子受体，包括CXCR4和CCR5，并且对人类免疫缺陷病毒（HIV）感染目标细胞具有保护作用。