3-phenyl-1-(4-toluenesulfonyl)pyrazol-5-amine | 92133-94-3

• 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-phenyl-1-(4-toluenesulfonyl)pyrazol-5-amine
• 英文别名: 3-phenyl-1-tosyl-1H-pyrazol-5-amine；2-(4-Methylphenyl)sulfonyl-5-phenylpyrazol-3-amine
• CAS: 92133-94-3
• 化学式: C₁₆H₁₅N₃O₂S
• 分子量: 313.38
• InChiKey: QZSCBSVCHCQDSO-UHFFFAOYSA-N

物化性质

• 沸点：
  574.1±60.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  86.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-phenyl-1-(4-toluenesulfonyl)pyrazol-5-amine 在 tris-(dibenzylideneacetone)dipalladium(0) 、 四丁基氟化铵 、 potassium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 N,5-diphenyl-1H-pyrazol-3-amine
  参考文献：
  名称：

  Pd‐Catalyzed N ‐Arylations of 3‐Aryl‐1‐tosyl‐1 H ‐pyrazol‐5‐amines with Arylbromides and the Migration of Ts Group

  摘要：

  AbstractAn efficient palladium‐catalyzed N‐arylations of 3‐aryl‐1‐tosyl‐1H‐pyrazol‐5‐amines with arylbromides is established. A series of diversified N‐arylated products are obtained in excellent yields with broad substrate scope. Importantly, the N‐arylated products undergo 1,4‐ and 1,6‐migration reactions of Ts group under the action of Cs2CO3, affording the N‐Ts‐substituted pyrroles as major products (1,6‐migration). Similar results can also be directly obtained by palladium‐catalyzed reactions of 3‐aryl‐1‐tosyl‐1H‐pyrazol‐5‐amines with arylbromides in the presence of Cs2CO3 as a base. Mechanistic studies reveal that the Ts‐migration is achieved through an intermolecular pathway.

  DOI：

  10.1002/cctc.202100193
• 作为产物：
  描述：

  4-iodo-3-phenyl-1-tosyl-1H-pyrazol-5-amine 在 一水合肼 作用下， 以 水 为溶剂， 反应 12.0h， 以60%的产率得到3-phenyl-1-(4-toluenesulfonyl)pyrazol-5-amine
  参考文献：
  名称：

  4-碘-1H-吡唑-5-胺与芳基磺酰肼在水中的C4-磺酰化

  摘要：

  开发了 4-iodine-1 H -pyrazole-5-amine 与芳基磺酰肼在水中的 C4-亚磺酰化反应。以中等至优异的产率获得了一系列 C4- 亚磺酰化产物。该协议具有绿色反应条件（无金属、水作为溶剂、在空气中）、无味且易于获得的硫试剂、广泛的底物范围以及克级合成。机理研究表明，在芳基磺酰肼存在下，4-iodine-1 H -pyrazole-5-amine 原位形成碘是C4-磺酰化反应的关键。

  DOI：

  10.1016/j.mcat.2022.112485

文献信息

• Halogenations of 3-Aryl-1H-pyrazol-5-amines
  作者：Bin Dai、Ping Liu、Jing He、Yueting Wei、Yijiao Feng、Chuntian Li

  DOI：10.1055/a-1684-0308

  日期：2022.4

  A direct C–H halogenation of 3-aryl-1H-pyrazol-5-amines using N-halogenosuccinimides (NXS; X = Br, I, Cl) in dimethyl sulfoxide at room temperature has been developed. This transformation provides an effective metal-free protocol for the synthesis of novel 4-halogenated pyrazole derivatives with moderate to excellent yields. The method utilizes NXS reagents as cheap and safe halogenating reagents under

  已经开发了在室温下在二甲基亚砜中使用 N-卤代琥珀酰亚胺（NXS；X = Br、I、Cl）对 3-芳基-1H-吡唑-5-胺进行直接 C-H 卤化。这种转化为合成具有中等至优异产率的新型 4-卤代吡唑衍生物提供了一种有效的无金属方案。该方法利用NXS试剂作为廉价、安全的卤化试剂，反应条件简单温和，底物范围广，可用于克级合成。该过程的效用是通过 4-卤化产物的进一步转化来建立的。机理研究表明，DMSO 具有催化剂和溶剂的双重作用。
• Synthesis of Diversified Pyrazolo[3,4-b]pyridine Frameworks from 5-Aminopyrazoles and Alkynyl Aldehydes via Switchable C≡C Bond Activation Approaches
  作者：Xiao-Yu Miao、Yong-Ji Hu、Fu-Rao Liu、Yuan-Yuan Sun、Die Sun、An-Xin Wu、Yan-Ping Zhu

  DOI：10.3390/molecules27196381

  日期：——

  cascade 6-endo-dig cyclization reaction was developed for the switchable synthesis of halogen and non-halogen-functionalized pyrazolo[3,4-b]pyridines from 5-aminopyrazoles and alkynyl aldehydes via C≡C bond activation with silver, iodine, or NBS. In addition to its wide substrate scope, the reaction showed good functional group tolerance as well as excellent regional selectivity. This new protocol

  开发了级联6-endo-dig环化反应，用于从 5-氨基吡唑和炔基醛通过 C≡C 键活化与银、碘、或国家统计局。除了底物范围广外，该反应还表现出良好的官能团耐受性和优异的区域选择性。这个新的协议操纵了三种天然产物，以及碘功能化产物的芳基化、炔基化、烯基化和硒化。这些反应证明了这种新方法的潜在应用。
• Ege, Guenter; Franz, Hermann, Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 689 - 695
  作者：Ege, Guenter、Franz, Hermann

  DOI：——

  日期：——
• EGE, G.;FRANZ, H., J. HETEROCYCL. CHEM., 1984, 21, N 3, 689-695
  作者：EGE, G.、FRANZ, H.

  DOI：——

  日期：——
• Pd‐Catalyzed <i>N</i> ‐Arylations of 3‐Aryl‐1‐tosyl‐1 <i>H</i> ‐pyrazol‐5‐amines with Arylbromides and the Migration of Ts Group
  作者：Jing He、Zhen Yang、Weiwei Li、Yueting Wei、Bin Dai、Jixing Zhao、Ping Liu

  DOI：10.1002/cctc.202100193

  日期：2021.6.8

  AbstractAn efficient palladium‐catalyzed N‐arylations of 3‐aryl‐1‐tosyl‐1H‐pyrazol‐5‐amines with arylbromides is established. A series of diversified N‐arylated products are obtained in excellent yields with broad substrate scope. Importantly, the N‐arylated products undergo 1,4‐ and 1,6‐migration reactions of Ts group under the action of Cs2CO3, affording the N‐Ts‐substituted pyrroles as major products (1,6‐migration). Similar results can also be directly obtained by palladium‐catalyzed reactions of 3‐aryl‐1‐tosyl‐1H‐pyrazol‐5‐amines with arylbromides in the presence of Cs2CO3 as a base. Mechanistic studies reveal that the Ts‐migration is achieved through an intermolecular pathway.