1-(4-chlorophenyl)-3,5-dimethyl-4-thiocyanato-1H-pyrazole | 92188-69-7

• 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-(4-chlorophenyl)-3,5-dimethyl-4-thiocyanato-1H-pyrazole
• 英文别名: [1-(4-Chlorophenyl)-3,5-dimethylpyrazol-4-yl] thiocyanate
• CAS: 92188-69-7
• 化学式: C₁₂H₁₀ClN₃S
• 分子量: 263.75
• InChiKey: ADBLFGBFTMQCBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对氯苯肼盐酸盐 在 lithium tetrafluoroborate 、 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 4.25h， 生成 1-(4-chlorophenyl)-3,5-dimethyl-4-thiocyanato-1H-pyrazole
  参考文献：
  名称：

  One‐Pot Synthesis of 4‐Thiocyanato‐1 H ‐pyrazoles through Electrochemical Multicomponent Thiocyanation under Metal‐ and Oxidant‐Free Conditions

  摘要：

  AbstractAn electrochemical oxidative three‐component tandem reaction of arylhydrazines, 1,3‐diketones and ammonium thiocyanate has been established to construct 4‐thiocyanato‐1H‐pyrazoles under metal‐, oxidant‐free and mild conditions in an undivided cell. Various 4‐thiocyanato‐1H‐pyrazole derivatives could be obtained with broad substrate scope, and excellent functional group tolerance from available raw materials in moderate to excellent yields. This thiocyanation protocol with practicability and scalability features economical and eco‐friendly.

  DOI：

  10.1002/ejoc.202201278

文献信息

• Synthesis of 4-functionalized pyrazoles via oxidative thio- or selenocyanation mediated by PhICl2 and NH4SCN/KSeCN
  作者：Jialiang Wu、Haofeng Shi、Xuemin Li、Jiaxin He、Chen Zhang、Fengxia Sun、Yunfei Du

  DOI：10.3762/bjoc.20.128

  日期：——

  Abstract A series of 4-thio/seleno-cyanated pyrazoles was conveniently synthesized from 4-unsubstituted pyrazoles using NH4SCN/KSeCN as thio/selenocyanogen sources and PhICl2 as the hypervalent iodine oxidant. This metal-free approach was postulated to involve the in situ generation of reactive thio/selenocyanogen chloride (Cl–SCN/SeCN) from the reaction of PhICl2 and NH4SCN/KSeCN, followed by an electrophilic

  抽象的 以NH 4 SCN/KSeCN为硫代/硒氰源，PhICl 2为高价碘氧化剂，以4-未取代吡唑为原料，方便地合成了一系列4-硫代/硒氰化吡唑。这种无金属方法被认为涉及通过 PhICl 2和 NH 4 SCN/KSeCN 的反应原位生成活性硫代/硒氰氯化物 (Cl–SCN/SeCN)，然后对吡唑骨架进行亲电硫代/硒氰化。 Beilstein J. Org. Chem. 2024, 20, 1453–1461. doi:10.3762/bjoc.20.128
• Visible-light enabled C4-thiocyanation of pyrazoles by graphite-phase carbon nitride (g-C3N4)
  作者：Junyi Pan、Cheng Liu、Jianqiang Wang、Yunqiao Dai、Shengyu Wang、Cheng Guo

  DOI：10.1016/j.tetlet.2021.153253

  日期：2021.8
• External electrolyte-free electrochemical one-pot cascade synthesis of 4-thiocyanato-1H-pyrazoles
  作者：Wei-Bao He、Sai-Jie Zhao、Jing-Yang Chen、Jun Jiang、Xiang Chen、Xinhua Xu、Wei-Min He

  DOI：10.1016/j.cclet.2022.06.063

  日期：2023.2