3,5-dimethyl-1-phenyl-4-thiocyanato-1H-pyrazole | 91843-62-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,5-dimethyl-1-phenyl-4-thiocyanato-1H-pyrazole
• 英文别名: (3,5-Dimethyl-1-phenylpyrazol-4-yl) thiocyanate
• CAS: 91843-62-8
• 化学式: C₁₂H₁₁N₃S
• 分子量: 229.305
• InChiKey: PFSXQJCDVNNIHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 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

• 作为反应物：
  描述：

  3,5-dimethyl-1-phenyl-4-thiocyanato-1H-pyrazole 在 sodium azide 作用下， 生成
  参考文献：
  名称：

  External electrolyte-free electrochemical one-pot cascade synthesis of 4-thiocyanato-1H-pyrazoles

  摘要：

  DOI：

  10.1016/j.cclet.2022.06.063
• 作为产物：
  描述：

  苯肼 在 氧气 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 53.0h， 生成 3,5-dimethyl-1-phenyl-4-thiocyanato-1H-pyrazole
  参考文献：
  名称：

  Visible-light enabled C4-thiocyanation of pyrazoles by graphite-phase carbon nitride (g-C3N4)

  摘要：

  DOI：

  10.1016/j.tetlet.2021.153253

文献信息

• Hydrogen Peroxide-Mediated Rapid Room Temperature Metal-Free C(sp²)-H Thiocyanation of Amino Pyrazoles, Amino Uracils, and Enamines
  作者：Danish Ali、Anoop Kumar Panday、Lokman H. Choudhury

  DOI：10.1021/acs.joc.0c01738

  日期：2020.11.6

  aminopyrazoles, aminoisoxazole, aminoisothiazole, amino uracils, and aliphatic enamines has been developed in an aqueous medium using hydrogen peroxide as a benign oxidant and ammonium thiocyanate as a thiocyanating agent. On the other hand, the reaction of hydrogen peroxide and ammonium thiocyanate followed by one-pot addition of NaOH provides the corresponding disulfides in the case of amino azoles, and

  已经开发了一种在水性介质中使用过氧化氢作为良性氧化剂和硫氰酸铵对氨基吡唑，氨基异恶唑，氨基异噻唑，氨基尿嘧啶和脂肪族烯胺进行C（sp 2）-H硫氰化的快速无金属室温室温方法作为硫氰化剂。另一方面，在氨基唑的情况下，过氧化氢和硫氰酸铵的反应，然后一锅加NaOH，提供了相应的二硫化物；在氨基尿嘧啶的情况下，观察到了嘧啶稠合的2-氨基噻唑。该方法的显着特征是使用了环保型氧化剂，反应可调性以获取不同的产品，广泛的底物范围以及良好的产率。
• 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
• One‐Pot Synthesis of 4‐Thiocyanato‐1 <i>H</i> ‐pyrazoles through Electrochemical Multicomponent Thiocyanation under Metal‐ and Oxidant‐Free Conditions
  作者：Ying Zhang、Sen Xu、Yutao Zhu、Qingyu Xu、Huanjie Gao、Zeyao Liang、Xiaoquan Yao

  DOI：10.1002/ejoc.202201278

  日期：2023.1.10

  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.