2-azido-1-benzyl-4,5,6,7-tetrahydro-1H-benzo[d]imidazole | 948037-96-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-azido-1-benzyl-4,5,6,7-tetrahydro-1H-benzo[d]imidazole
• 英文别名: 2-Azido-4,5,6,7-tetrahydro-1-(phenylmethyl)-1H-benzimidazole；2-azido-1-benzyl-4,5,6,7-tetrahydrobenzimidazole
• CAS: 948037-96-5
• 化学式: C₁₄H₁₅N₅
• 分子量: 253.307
• InChiKey: DXZCAHDUYBJVFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  32.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-azido-1-benzyl-4,5,6,7-tetrahydro-1H-benzo[d]imidazole 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以98%的产率得到1-Benzyl-4,5,6,7-tetrahydrobenzimidazol-2-amine
  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：

  1-benzyl-4,5,6,7-tetrahydro-1H-benzimidazole 在 正丁基锂 、 对甲苯磺酰叠氮 作用下， 以 四氢呋喃 为溶剂， 以60%的产率得到2-azido-1-benzyl-4,5,6,7-tetrahydro-1H-benzo[d]imidazole
  参考文献：
  名称：

  硫辛酸介导的叠氮化物向酰胺的转化——2-叠氮基四氢苯并咪唑及其衍生物的研究

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2020.152484

文献信息

• Oxidation reactions using polymer-supported 2-benzenesulfonyl-3-(4-nitrophenyl)oxaziridine
  作者：Woen Susanto、Yulin Lam

  DOI：10.1016/j.tet.2011.08.058

  日期：2011.10

  A thermally stable polymer-supported oxidant has been developed. Polymer-supported 2-benzenesulfonyl-3-(4-nitrophenyl)oxaziridine was applied to microwave-assisted reactions that occurred at high temperatures and was shown to oxidize alkenes, silyl enol ethers, and pyridines to the corresponding epoxides and pyridine N-oxides in excellent to good yields and with much shorter reaction times. It also

  已经开发出热稳定的聚合物负载氧化剂。聚合物负载的 2-苯磺酰基-3-(4-硝基苯基)氧氮丙啶应用于高温下发生的微波辅助反应，并被证明可以将烯烃、硅烯醇醚和吡啶氧化成相应的环氧化物和吡啶 N-氧化物产率极好至良好，反应时间短得多。它还使得四氢苯并咪唑能够以更有效的方式氧化重排为螺稠合的5-咪唑酮。聚合物负载的氧化剂的回收也是可能的，并且在几次再氧化后活性损失最小。
• Oxidative reactions of tetrahydrobenzimidazole derivatives with N-sulfonyloxaziridines
  作者：Rasapalli Sivappa、Panduka Koswatta、Carl J. Lovely

  DOI：10.1016/j.tetlet.2007.06.088

  日期：2007.8

  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.
• 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。