N,N-二甲基苯并咪唑-1-磺酰胺 | 349422-98-6

• 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: N,N-二甲基苯并咪唑-1-磺酰胺
• 英文名称: 1-(N,N-dimethylsulfamoyl)-benzimidazole
• 英文别名: 1-dimethylsulfamoyl-1H-benzimidazole；N,N-Dimethyl benzoimidazole-1-sulfonamide；N,N-dimethylbenzimidazole-1-sulfonamide
• CAS: 349422-98-6
• 化学式: C₉H₁₁N₃O₂S
• 分子量: 225.271
• InChiKey: XDXIDHANDJYSQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  N,N-二甲基苯并咪唑-1-磺酰胺 在 sodium tetrahydroborate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 3.75h， 生成 2-((R)-{(4S,5R)-5-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-hydroxy-methyl)-benzoimidazole-1-sulfonic acid dimethylamide
  参考文献：
  名称：

  立体控制合成的杂环C-核苷。保护基团效应和分子模型研究。

  摘要：

  我们在此报告了杂环C-核苷（吲哚，咪唑，苯并咪唑和6-碘代苯并咪唑）的短立体控制合成。首先，2-锂化的杂环2-5与5-（叔丁基二苯基甲硅烷基）-2，3-O-异亚丙基-D-γ-核糖内酯（1）的缩合以高收率得到半缩醛6-9。然后，将受保护的半缩醛的硼氢化物还原反应（NaBH（4））立体选择性地进行，主要得到S二醇10-13，经Mitsunobu环化，得到的α-C-核苷14-17。相反，相同的PPh（3）/ DEAD处理游离杂环二醇10d和11d的1：1非对映混合物，分别通过立体控制过程分别获得了β-端基异构体14dbeta和15dbeta。在分子模型研究的支持下，讨论了这些立体控制步骤的机理。

  DOI：

  10.1021/jo016345x
• 作为产物：
  描述：

  5-烯丙基-4-(1-羟基烯丙基)-N,N-二甲基-1H-咪唑-1-磺酰胺 在 Grubbs catalyst first generation 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以45%的产率得到N,N-二甲基苯并咪唑-1-磺酰胺
  参考文献：
  名称：

  Synthesis of fused bicyclic imidazoles by ring-closing metathesis

  摘要：

  The preparation of a number of dienylimidazole via chemoselective metal-halogen exchange and their utility in ring-closing metathesis is described. Essentially all regioisomeric permutations participate in metathesis with the notable exception of 4-vinyl-5-allylimidazoles, provided that the imidazole N3 atom is protonated. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02864-2

文献信息

• Efficient stereocontrolled synthesis of 2-benzimidazolyl- and 2-indolyl-C-nucleosides
  作者：Dominique Guianvarc'h、Rachid Benhida、Jean-Louis Fourrey

  DOI：10.1016/s0040-4039(00)02029-3

  日期：2001.1

  We report herein the synthesis of β-2-benzimidazolyl- and β-2-indolyl-C-nucleosides and their α-anomers in a stereoselective way. The stereocontrol was observed either in the reduction step (hemiacetal to diol) of the protected heterocycles (1b–d), or in the intramolecular Mitsunobu cyclisation of the free heterocyclic diols obtained from the hemiacetals 1a and 1e.

  我们在此报告β-2- benzimidazolyl-和β-2-吲哚基的合成Ç以立体选择性方式核苷和它们的α端基异构体。在受保护的杂环（1b – d）的还原步骤（半缩醛制为二醇）中，或在从半缩醛1a和1e获得的游离杂环二醇的分子内光延环化中，均观察到了立体控制。
• Inhibitors Of Fatty Acid Amide Hydrolase And Monoacylglycerol Lipase For Modulation Of Cannabinoid Receptors
  申请人：Northeastern University

  公开号：US20160139162A1

  公开（公告）日：2016-05-19

  Disclosed are compounds and compositions that inhibit the action of fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MGL), methods of inhibiting FAAH and MGL, methods of modulating cannabinoid receptors, and methods of treating various disorders related to modulation of cannabinoid receptors.

  本发明涉及抑制脂肪酸酰胺水解酶（FAAH）和单酰基甘油脂肪酶（MGL）作用的化合物和组合物，抑制FAAH和MGL的方法，调节大麻素受体的方法，以及治疗与大麻素受体调节相关的各种疾病的方法。
• Synthesis of fused bicyclic imidazoles by ring-closing metathesis
  作者：Yingzhong Chen、H.V.Rasika Dias、Carl J. Lovely

  DOI：10.1016/s0040-4039(02)02864-2

  日期：2003.2

  The preparation of a number of dienylimidazole via chemoselective metal-halogen exchange and their utility in ring-closing metathesis is described. Essentially all regioisomeric permutations participate in metathesis with the notable exception of 4-vinyl-5-allylimidazoles, provided that the imidazole N3 atom is protonated. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis, Incorporation into Triplex-Forming Oligonucleotide, and Binding Properties of a Novel 2‘-Deoxy-<i>C</i>-Nucleoside Featuring a 6-(Thiazolyl-5)benzimidazole Nucleobase
  作者：Dominique Guianvarc'h、Jean-Louis Fourrey、Rosalie Maurisse、Jian-Sheng Sun、Rachid Benhida

  DOI：10.1021/ol026609h

  日期：2002.11.1

  6-(Thiazolyl-5)benzimidazole (B-1) was designed as a novel nucleobase for the specific recognition of an inverted A(.)T base pair in a triple helix motif. It was successfully incorporated into an 18-mer triplex-forming oligonucleotide (TFO) using the 2'-deoxy-C-nucleoside phosphoramidite 16. The triple helix binding properties of the modified TFO were examined by means of thermal denaturation experiments targeting an oligopyrimidine-oligopurine 26-mer DNA duplex containing an A-T base pair inversion.
• Ring Closing Metathesis Reactions of Imidazole Derivatives
  作者：Carl J. Lovely、Yingzhong Chen、E. Vindana Ekanayake

  DOI：10.3987/com-07-s(w)83

  日期：——