1-环己基-5-苯基-1H-四唑 | 100616-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-环己基-5-苯基-1H-四唑
• 英文名称: 1-cyclohexyl-5-phenyl-1H-tetrazole
• 英文别名: 1-cyclohexyl-5-phenyl-1H-tetrazole；1-Cyclohexyl-5-phenyl-1H-tetrazol；1-Cyclohexyl-5 phenyltetrazole；1-cyclohexyl-5-phenyltetrazole
• CAS: 100616-90-8
• 化学式: C₁₃H₁₆N₄
• 分子量: 228.297
• InChiKey: POPGDDHQOXNEQZ-UHFFFAOYSA-N

物化性质

• 熔点：
  132-133 °C
• 沸点：
  396.3±25.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-cyclohexyl-thiobenzamide 在 三乙胺 、 2-碘酰基苯甲酸 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以74%的产率得到1-环己基-5-苯基-1H-四唑
  参考文献：
  名称：

  o-Iodoxybenzoic Acid Mediated Oxidative Desulfurization Initiated Domino Reactions for Synthesis of Azoles

  摘要：

  A systematic exploration of thiophilic ability of o-iodoxybenzoic acid (IBX) for oxidative desulfurization to trigger domino reactions leading to new methodologies for synthesis of different azoles is described. A variety of highly substituted oxadiazoles, thiadiazoles, triazoles, and tetrazoles have been successfully synthesized in good to excellent yields, starting from readily accessible thiosemicarbazides, bis-diarylthiourea, 1,3-disubtituted thiourea, and thioamides.

  DOI：

  10.1021/jo2025509

文献信息

• An Expeditious Approach to Tetrazoles from Amides Utilizing Phosphorazidates
  作者：Kotaro Ishihara、Takayuki Shioiri、Masato Matsugi

  DOI：10.1021/acs.orglett.0c01890

  日期：2020.8.21

  A novel method was developed for the synthesis of tetrazoles from amides utilizing diphenyl phosphorazidate or bis(p-nitrophenyl) phosphorazidate as both the activator of amide–oxygen for elimination and azide source. Various amides were converted into the corresponding tetrazoles in good yields. This synthetic method allows to prepare 1,5-disubstituted and 5-substituted 1H-tetrazoles from various

  开发了一种新的方法，该方法利用叠氮基磷酸二苯酯或叠氮基双（对硝基苯基）磷酸酯作为酰胺-氧消除和叠氮化物的活化剂，从酰胺中合成四唑。各种酰胺以良好的产率转化为相应的四唑。该合成方法允许由各种酰胺制备1，5-二取代和5-取代的1 H-四唑，而无需使用有毒或易爆的试剂。
• Three-Component Strategy toward 5-Membered Heterocycles from Isocyanide Dibromides.
  作者：Laurent El Kaim、Laurence Grimaud、Pravin Patil

  DOI：10.1021/ol200003u

  日期：2011.3.4

  A three-component strategy starting from isocyanides allows a straightforward synthesis of five-membered ring heterocycles. New cascades were developed involving the addition of a nitrogenated nucleophile—an azide or a tetrazole—on isocyanide dibromides, an electrocyclization, and a Suzuki coupling, which afford new accesses to tetrazole and triazole scaffolds.

  从异氰酸酯开始的三组分策略允许直接合成五元环杂环。开发了新的级联反应，包括在异氰酸酯二溴化物上添加氮化的亲核试剂（叠氮化物或四唑），电环化和Suzuki偶联，为四唑和三唑骨架提供了新途径。
• Practical synthesis of tetrazoles from amides and phosphorazidates in the presence of aromatic bases
  作者：Kotaro Ishihara、Kazuki Ishihara、Yota Tanaka、Takayuki Shioiri、Masato Matsugi

  DOI：10.1016/j.tet.2022.132642

  日期：2022.2

  Tetrazoles were effectively synthesized from amides using diphenyl phosphorazidate or bis(p-nitrophenyl) phosphorazidate in the presence of aromatic bases. Various amides underwent the proposed cycloaddition reaction to provide the corresponding tetrazoles. Studies on the racemization of chiral substrates were also performed. Overall, the proposed synthesis method enables the preparation of 1,5-disubstituted

  在芳族碱的存在下，使用叠氮化磷酸二苯酯或双（对硝基苯基）叠氮化磷酸酯由酰胺有效地合成了四唑。各种酰胺经历了所提出的环加成反应以提供相应的四唑。还进行了手性底物外消旋化的研究。总体而言，所提出的合成方法能够在不使用有毒或爆炸性试剂的情况下制备 1,5-二取代和 1-取代四唑和 5-取代 1 H-四唑。
• Direct C−H Arylation and Alkenylation of 1-Substituted Tetrazoles: Phosphine As Stabilizing Factor
  作者：Marcel Špulák、Richard Lubojacký、Petr Šenel、Jiří Kuneš、Milan Pour

  DOI：10.1021/jo902180u

  日期：2010.1.1

  Direct arylation and alkenylation of 1-substituted tetrazoles was achieved via Pd catalysis in the presence of CuI and CS2CO3. Unlike the related reactions of imidazoles and purines, phosphine ligand was necessary to prevent the intermediate tetrazolyl-Pd-II species from fragmentation into the corresponding cyanamide, Various 1,5-disubstituted tetrazoles were prepared with good to excellent isolated yields.
• Additions of 5-phenyltetrazole and other heterocyclic NH compounds to olefins
  作者：Alan R. Katritzky、Ming Qi、Adam P. Wells

  DOI：10.1007/bf01169962

  日期：——