(Z)-1-(4-phenylbut-3-yn-2-ylidene)-2-(4-(trifluoromethyl)phenyl)hydrazine | 1318808-02-4

• 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: (Z)-1-(4-phenylbut-3-yn-2-ylidene)-2-(4-(trifluoromethyl)phenyl)hydrazine
• 英文别名: N-[(Z)-4-phenylbut-3-yn-2-ylideneamino]-4-(trifluoromethyl)aniline
• CAS: 1318808-02-4
• 化学式: C₁₇H₁₃F₃N₂
• 分子量: 302.299
• InChiKey: FAHIUJPYOIAYFC-BKUYFWCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-1-(4-phenylbut-3-yn-2-ylidene)-2-(4-(trifluoromethyl)phenyl)hydrazine 在 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以78%的产率得到3-methyl-5-phenyl-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole
  参考文献：
  名称：

  Synthesis of Pyrazoles via CuI-Mediated Electrophilic Cyclizations of α,β-Alkynic Hydrazones

  摘要：

  Synthesis of pyrazoles via electrophilic cyclization of alpha,beta-alkynic hydrazones by copper(I) iodide is described. When treated with copper(I) iodide in the presence of triethylamine in refluxing acetonitrile, alpha,beta-alkynic hydrazones, prepared readily from hydrazines and propargyl aldehydes and ketones, undergo electrophilic cyclization to afford pyrazole derivatives in good to excellent yields. The reaction appears to be general for a variety of alpha,beta-alkynic hydrazones and tolerates the presence of aliphatic, aromatic, and ferrocenyl moieties with electron-withdrawing and electron-donating substituents.

  DOI：

  10.1021/jo201685p
• 作为产物：
  描述：

  苯乙炔 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (Z)-1-(4-phenylbut-3-yn-2-ylidene)-2-(4-(trifluoromethyl)phenyl)hydrazine
  参考文献：
  名称：

  Synthesis of Pyrazoles via Electrophilic Cyclization

  摘要：

  Electrophilic cyclizations of alpha,beta-alkynic hydrazones by molecular iodine were investigated for the synthesis of 4-iodopyrazoles. alpha,beta-Alkynic hydrazones were readily prepared by the reactions of hydrazines with propargyl aldehydes and ketones. When treated with molecular iodine in the presence of sodium bicarbonate, alpha,beta-alkynic hydrazones underwent electrophilic cyclization to afford 4-iodopyrazoles in good to high yields. Iodocyclization was general for a wide range of alpha,beta-alkynic hydrazones and tolerated the presence of aliphatic, aromatic, heteroaromatic, and ferrocenyl moieties with electron-withdrawing and electron-donating substituents.

  DOI：

  10.1021/jo201119e

文献信息

• Synthesis of Pyrazoles via CuI-Mediated Electrophilic Cyclizations of α,β-Alkynic Hydrazones
  作者：Metin Zora、Arif Kivrak

  DOI：10.1021/jo201685p

  日期：2011.11.18

  Synthesis of pyrazoles via electrophilic cyclization of alpha,beta-alkynic hydrazones by copper(I) iodide is described. When treated with copper(I) iodide in the presence of triethylamine in refluxing acetonitrile, alpha,beta-alkynic hydrazones, prepared readily from hydrazines and propargyl aldehydes and ketones, undergo electrophilic cyclization to afford pyrazole derivatives in good to excellent yields. The reaction appears to be general for a variety of alpha,beta-alkynic hydrazones and tolerates the presence of aliphatic, aromatic, and ferrocenyl moieties with electron-withdrawing and electron-donating substituents.
• Synthesis of Pyrazoles via Electrophilic Cyclization
  作者：Metin Zora、Arif Kivrak、Ceyda Yazici

  DOI：10.1021/jo201119e

  日期：2011.8.19

  Electrophilic cyclizations of alpha,beta-alkynic hydrazones by molecular iodine were investigated for the synthesis of 4-iodopyrazoles. alpha,beta-Alkynic hydrazones were readily prepared by the reactions of hydrazines with propargyl aldehydes and ketones. When treated with molecular iodine in the presence of sodium bicarbonate, alpha,beta-alkynic hydrazones underwent electrophilic cyclization to afford 4-iodopyrazoles in good to high yields. Iodocyclization was general for a wide range of alpha,beta-alkynic hydrazones and tolerated the presence of aliphatic, aromatic, heteroaromatic, and ferrocenyl moieties with electron-withdrawing and electron-donating substituents.