3,5-diphenyl-4-cyanopyrazole | 101727-68-8

• 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-diphenyl-4-cyanopyrazole
• 英文别名: 3,5-diphenyl-1H-pyrazole-4-carbonitrile；3,5-Diphenyl-1H-pyrazol-4-carbonitril
• CAS: 101727-68-8
• 化学式: C₁₆H₁₁N₃
• 分子量: 245.283
• InChiKey: IXYLGZGNXRSDRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氰基-1,3-二苯基-1,3-丙二酮 在 一水合肼 作用下， 以 甲醇 为溶剂， 以3.6 g的产率得到3,5-diphenyl-4-cyanopyrazole
  参考文献：
  名称：

  New trisubstituted cyanopyrazoles and cyanoscorpionates

  摘要：

  New syntheses are reported to give pyrazoles with cyano substituents at the 4-position of the pyrazole ring and ethyl or isopropyl substituents at the 3-position, as well as pyrazoles with cyano substituents at the 4-position and alkyl/aryl/bromo substituents at both the 3-and 5-positions. Synthesis of scorpionates using tetradecane as a high-boiling solvent has been shown to be more efficient than the melt method and has led to new scorpionates using the newly synthesized pyrazoles. An unexpected complex is isolated in which the Ni(cyclam)2(+) moiety crystallizes with two cyanoscorpionates as counterions, without binding of the scorpionate ligands to the Ni atom. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2016.12.016

文献信息

• Electrophilic α-cyanation of 1,3-dicarbonyl compounds
  作者：Ramulu Akula、Yan Xiong、Hasim Ibrahim

  DOI：10.1039/c3ra41376d

  日期：——

  Electrophilic α-cyanation of activated methylene compounds was achieved under mild basic conditions using commercially available TsCN as a CN+ equivalent. A series of 1,3-dicarbonyl compounds, both cyclic and acyclic, were found to be suitable substrates for this transformation. Subjecting 1,1,1-trifluoro-1,3-dicarbonyl compounds to a modified procedure resulted in the formation of α-cyano ketones

  使用市售的TsCN作为CN +等效物，在温和的碱性条件下实现了活化亚甲基化合物的亲电α-氰化。发现一系列环状和非环状的1，3-二羰基化合物是该转化的合适底物。使1,1,1-三氟-1,3-二羰基化合物经过改进的程序导致三氟乙酰基断裂后形成α-氰基酮。还开发了一种有效的一锅氰化/吡唑从1，3-二酮生成4-氰基吡唑的顺序。
• Sprio; Fabra, Gazzetta Chimica Italiana, 1956, vol. 86, p. 1059,1064
  作者：Sprio、Fabra

  DOI：——

  日期：——
• The conversion of isothiazoles into pyrazoles using hydrazine
  作者：Heraklidia A. Ioannidou、Panayiotis A. Koutentis

  DOI：10.1016/j.tet.2009.06.041

  日期：2009.8

  The conversion of isothiazoles into pyrazoles on treatment with hydrazine is investigated. The influence of various C-3, C-4 and C-5 isothiazole substituents and some limitations of this ring transformation are examined. When the isothiazole C-3 substituent is a good nucleofuge, 3-aminopyrazoles are obtained. However, when the 3-substituent is not a leaving group it is retained in the pyrazole product. Treatment of 4-bromo-3-chloro-5-phenylisothiazoie 56 or 3-chloro-4,5-diphenylisothiazole 57 with anhydrous hydrazine at ca. 200 degrees C for a few minutes gives the corresponding 3-hydrazinoisothiazoles 61 and 64 respectively in high yields; the stability of these new hydrazines is investigated. 5,5'-Diphenyl-3,3'-biisothiazole-4,4'-dicarbonitrile 78 reacts with hydrazine to give 5,5'-diphenyl-3,3'-bi(1H-pyi-azole)-4,4'-dicarbonitrile 79. Methylhydrazine reacts with 3-chloro-5-phenytisothiazole-4-carbonitrile 1 to give 3-(1-methylhydrazino)-5-phenylisothiazole-4-carbontrile 83 and 3-amino-lmethyl-5-phenylpyrazole-4-carbonitrile 84. All products are fully characterised and rational mechanisms for the isothiazole into pyrazole transformation are proposed. (C) 2009 Elsevier Ltd. All rights reserved.