1-benzoyl-4-(tert-butyl)thiosemicarbazide | 261705-10-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzoyl-4-(tert-butyl)thiosemicarbazide
• 英文别名: 1-Benzamido-3-tert-butylthiourea
• CAS: 261705-10-6
• 化学式: C₁₂H₁₇N₃OS
• 分子量: 251.352
• InChiKey: FTFGKBPHJXGJQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  85.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzoyl-4-(tert-butyl)thiosemicarbazide 在 三乙胺 、 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 N-tert-butyl-5-phenyl-1,3,4-oxadiazol-2-amine
  参考文献：
  名称：

  高价碘（V）介导轻度和方便地合成取代的2-氨基-1,3,4-恶二唑

  摘要：

  已经描述了一种简单的方案，该方案通过由邻碘代碘苯甲酸介导的中间体酰基硫代氨基脲在高产率下进行环脱硫，从相应的酰肼开始合成2-氨基-1,3,4-恶二唑。该方案温和，底物范围广，因此已制备了一系列的2-氨基-1,3,4-恶二唑。

  DOI：

  10.1016/j.tetlet.2012.05.154
• 作为产物：
  描述：

  叔丁基异硫氰酸酯 、 苯甲酰肼 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-benzoyl-4-(tert-butyl)thiosemicarbazide
  参考文献：
  名称：

  高价碘（V）介导轻度和方便地合成取代的2-氨基-1,3,4-恶二唑

  摘要：

  已经描述了一种简单的方案，该方案通过由邻碘代碘苯甲酸介导的中间体酰基硫代氨基脲在高产率下进行环脱硫，从相应的酰肼开始合成2-氨基-1,3,4-恶二唑。该方案温和，底物范围广，因此已制备了一系列的2-氨基-1,3,4-恶二唑。

  DOI：

  10.1016/j.tetlet.2012.05.154

文献信息

• The rapid preparation of 2-aminosulfonamide-1,3,4-oxadiazoles using polymer-supported reagents and microwave heating
  作者：Ian R. Baxendale、Steven V. Ley、Marisa Martinelli

  DOI：10.1016/j.tet.2005.03.062

  日期：2005.5

  Herein, we report on the preparation of a library of 5-substituted-2-amino-1,3,4-oxadiazoles and the corresponding thiadiazole analogues. Presented is a one-pot preparation of the 2-ammosulfonylated analogues through a three component coupling of an acylhydrazine, an isocyanate and sulfonyl chloride promoted by a polymer-supported phosphazine base under microwave dielectric heating. Also described is the optimization process and details pertaining to the elucidation of the reaction products. (c) 2005 Elsevier Ltd. All rights reserved.
• Catalytic Production of Isothiocyanates via a Mo(II)/Mo(IV) Cycle for the “Soft” Sulfur Oxidation of Isonitriles
  作者：Wesley S. Farrell、Peter Y. Zavalij、Lawrence R. Sita

  DOI：10.1021/acs.organomet.6b00302

  日期：2016.7.25

  In the presence of excess amounts of elemental sulfur, the dimolybdenum dinitrogen complex Cp*Mo[N(Pr-i)C(Ph)N(Pr-i)]}(2)(mu-N-2) (4; Cp* = eta(5)-C5Me8) serves as a precatalyst for the production of isothiocyanates from isonitriles via highly efficient and atom-economical metal-mediated sulfur atom transfer (SAT) under mild conditions. Mechanistic and structural studies support a catalytic cycle for SAT involving initial formation of a Mo(II) bis(isonitrile) complex that then undergoes sulfination to generate a formal "side-bound" Mo(IV) kappa(2)-(C,S)-isothiocyanate as the key intermediate. This metal-catalyzed SAT process has further been employed for the "on-demand" production of isothiocyanates that are trapped in situ by benzhydrazides to provide thiosemicarbazides, which are useful precursors to biologically active thiadiazoles.
• Development of 3,5-Dinitrophenyl-Containing 1,2,4-Triazoles and Their Trifluoromethyl Analogues as Highly Efficient Antitubercular Agents Inhibiting Decaprenylphosphoryl-β-<scp>d</scp>-ribofuranose 2′-Oxidase
  作者：Galina Karabanovich、Jan Dušek、Karin Savková、Oto Pavliš、Ivona Pávková、Jan Korábečný、Tomáš Kučera、Hana Kočová Vlčková、Stanislav Huszár、Zuzana Konyariková、Klára Konečná、Ondřej Jand’ourek、Jiřina Stolaříková、Jana Korduláková、Kateřina Vávrová、Petr Pávek、Věra Klimešová、Alexandr Hrabálek、Katarína Mikušová、Jaroslav Roh

  DOI：10.1021/acs.jmedchem.9b00912

  日期：2019.9.12

  We report herein the discovery of 3,5-dinitrophenyl 1,2,4-triazoles with excellent and selective antimycobacterial activities against Mycobacterium tuberculosis strains, including clinically isolated multidrug-resistant strains. Thorough structure activity relationship studies of 3,5-dinitrophenyl-containing 1,2,4-triazoles and their trifluoromethyl analogues revealed the key role of the position of the 3,5-dinitrophenyl fragment in the antitubercular efficiency. Among the prepared compounds, the highest in vitro antimycobacterial activities against M. tuberculosis H(37)Rv and against seven clinically isolated multidrug-resistant strains of M. tuberculosis were found with S-substituted 4-alkyl-5-(3,5-dinitrophenyl)-4H-1,2,4-triazole-3-thiols and their 3-nitro-5-(trifluoromethyl)phenyl analogues. The minimum inhibitory concentrations of these compounds reached 0.03 mu M, which is superior to all the current first-line anti-tuberculosis drugs. Furthermore, almost all compounds with excellent antimycobacterial activities exhibited very low in vitro cytotoxicities against two proliferating mammalian cell lines. The docking study indicated that these compounds acted as the inhibitors of decaprenylphosphoryl-beta-D-ribofuranose 2'-oxidase enzyme, which was experimentally confirmed by two independent radiolabeling experiments.
• Hypervalent iodine(V) mediated mild and convenient synthesis of substituted 2-amino-1,3,4-oxadiazoles
  作者：Girish Prabhu、V.V. Sureshbabu

  DOI：10.1016/j.tetlet.2012.05.154

  日期：2012.8

  A simple protocol for the synthesis of 2-amino-1,3,4-oxadiazoles starting from the corresponding acylhydrazides by cyclodesulfurization of intermediate acylthiosemicarbazides mediated by o-iodoxybenzoic acid in good yields has been described. The protocol is mild with wide substrate scope, and thus a range of 2-amino-1,3,4-oxadiazoles have been prepared.

  已经描述了一种简单的方案，该方案通过由邻碘代碘苯甲酸介导的中间体酰基硫代氨基脲在高产率下进行环脱硫，从相应的酰肼开始合成2-氨基-1,3,4-恶二唑。该方案温和，底物范围广，因此已制备了一系列的2-氨基-1,3,4-恶二唑。