(Z)-1-phenyl-2-(3-phenylprop-2-yn-1-ylidene)hydrazine | 1318807-91-8

• 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-phenyl-2-(3-phenylprop-2-yn-1-ylidene)hydrazine
• 英文别名: phenylpropynal phenylhydrazone；N-[(Z)-3-phenylprop-2-ynylideneamino]aniline
• CAS: 1318807-91-8
• 化学式: C₁₅H₁₂N₂
• 分子量: 220.274
• InChiKey: UJMNIDAVROFHPR-SSZFMOIBSA-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：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-1-phenyl-2-(3-phenylprop-2-yn-1-ylidene)hydrazine 在 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以77%的产率得到1,5 -二苯基- 1H -吡唑
  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-phenyl-2-(3-phenylprop-2-yn-1-ylidene)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

• Facile synthesis of alkynyl-, aryl- and ferrocenyl-substituted pyrazoles via Sonogashira and Suzuki-Miyaura approaches
  作者：Sedef Karabiyikoglu、Metin Zora

  DOI：10.1002/aoc.3516

  日期：2016.10

  dimethylformamide–H2O solution at 110 °C. Both Sonogashira and Suzuki–Miyaura coupling reactions have proven effective for the synthesis of alkynyl‐, aryl‐ and ferrocenyl‐substituted pyrazoles and demonstrated good tolerance to a diverse range of substituents, including electron‐donating and electron‐withdrawing groups. These coupling approaches could allow for the rapid construction of a library of functionalized

  简明高效地合成了具有炔基，芳基和二茂铁基官能团的高取代度新型吡唑，为生物学研究提供了平台。一般策略涉及易于获得的5-二茂铁基/苯基-4-碘--1-苯基吡唑分别与末端炔烃和硼酸发生的Sonogashira和Suzuki-Miyaura交叉偶联反应。起始的4-碘吡唑是通过α，β-炔β与分子碘的亲电环化反应合成的。的Sonogashira反应已经通过采用5％（摩尔）的PdCl实现2（PPH 3）2，5％（摩尔）的CuI，过量的Et 3N和1.2当量 在65°C的四氢呋喃中，相对于4-碘吡唑，末端炔烃的合成量为5％，而Suzuki–Miyaura反应已使用5 mol％PdCl 2（PPh 3）2和1.4当量完成。硼酸/酯和KHCO 3相对于4-碘吡唑在4：1二甲基甲酰胺– H 2中的含量O溶液在110°C。Sonogashira和Suzuki-Miyaura偶联反应均被证明对炔基，芳基和二茂铁基取