1-苯基-2-(2,2,2-三氟-1-苯基亚乙基)肼 | 82802-84-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-苯基-2-(2,2,2-三氟-1-苯基亚乙基)肼
• 英文名称: Trifluoroacetophenone phenylhydrazone
• 英文别名: N-[(2,2,2-trifluoro-1-phenylethylidene)amino]aniline
• CAS: 82802-84-4
• 化学式: C₁₄H₁₁F₃N₂
• 分子量: 264.25
• InChiKey: UHAGFVVYDHZPBD-UHFFFAOYSA-N

物化性质

• 沸点：
  292.9±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  1-苯基-2-(2,2,2-三氟-1-苯基亚乙基)肼 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以63%的产率得到3-phenylcinnolin-4-amine
  参考文献：
  名称：

  Trifluoromethyl group in the synthesis of heterocyclic compounds: New and efficient synthesis of 3-aryl-4-aminocinnolines

  摘要：

  A novel base induced transformation of hydrazones 3a-f derived from trifluoromethylaryl ketones and arylhydrazines was found to produce 3-aryl-4-aminocinnolines 4a-g in 52-75% yield. The initial step of the reaction is believed to involve abstraction of Hf from hydrazone.

  DOI：

  10.1016/0040-4039(95)00005-w
• 作为产物：
  描述：

  2,2,2-三氟苯乙酮 、 苯肼 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 1-苯基-2-(2,2,2-三氟-1-苯基亚乙基)肼
  参考文献：
  名称：

  吲唑和氮杂吲唑的合成分子内有氧氧化Ç ？无过渡金属条件下的N耦合

  摘要：

  过渡金属-自由氧化Ç  N个耦合方法已为1的合成开发ħ -azaindazoles 1个ħ从容易获得腙-indazoles。该程序使用TEMPO（一种碱性添加剂）和双氧气体作为终端氧化剂。与可比的金属催化反应相比，该反应显示出更好的反应性，官能团耐受性和更宽的范围。

  DOI：

  10.1002/chem.201304923

文献信息

• Synthesis of Chiral Trifluoromethyl-Substituted Hydrazines via Pd-Catalyzed Asymmetric Hydrogenation and Reductive Amination
  作者：Zhang-Pei Chen、Shu-Bo Hu、Ji Zhou、Yong-Gui Zhou

  DOI：10.1021/acscatal.5b01641

  日期：2015.10.2

  An efficient approach toward the synthesis of cyclic and linear chiral trifluoromethyl substituted hydrazines was developed by Pd-catalyzed asymmetric hydrogenation of both N-acyl and N-aryl hydrazones in excellent yields and up to 97% ee. A successful reductive amination between trifluoromethyl substituted ketones and hydrazines was also achieved.

  通过钯催化N-酰基和N-芳基的不对称氢化，以优异的收率和高达97％的ee ，开发了一种有效的合成环状和线性手性三氟甲基取代的肼的方法。在三氟甲基取代的酮和肼之间也成功实现了还原胺化。
• Anion-Driven C–F Bond Activation of Trifluoromethyl <i>N</i>-Aryl Hydrazones: Application to the Synthesis of 1,3,4-Oxadiazoles
  作者：Qijie Zou、Wei Zhang、Haoyue Wang、Guangwei Yin、Yongzhi He、Fangyi Li

  DOI：10.1021/acs.joc.3c01822

  日期：2023.11.3

  The CF3 group attached to N-aryl hydrazone could be activated upon treatment with a suitable base, thus serving as an excellent C1 unit for the assembly of a series of 1,3,4-oxadiazoles by reaction with hydrazides. The transformation is proposed to proceed via the intermediate formation of a gem-difluorinated azoalkene. Furthermore, this reaction features simple conditions and a broad substrate scope

  连接到N-芳基腙上的CF 3基团在用合适的碱处理后可以被活化，从而成为通过与酰肼反应组装一系列1,3,4-恶二唑的优异C1单元。提议该转化通过中间体形成偕二氟化偶氮烯来进行。此外，该反应条件简单，底物范围广，适用于三氟甲基N-芳基腙和酰肼。
• An efficient transition-metal-free synthesis of 1H-indazoles from arylhydrazones with montmorillonite K-10 under O2 atmosphere
  作者：Jin Yu、Jin Woo Lim、Su Yeon Kim、Jimin Kim、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2015.01.183

  日期：2015.3

  An efficient transition-metal-free synthetic method of 1H-indazoles has been developed. The reaction of arylhydrazones in the presence of montmorillonite K-10 in 1,2-dichlorobenzene at 130 degrees C afforded 1Hindazoles in good yields most likely via a sequential intramolecular nucleophilic cyclization and an aerobic oxidation pathway. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis of Indazoles and Azaindazoles by Intramolecular Aerobic Oxidative CN Coupling under Transition-Metal-Free Conditions
  作者：Jiantao Hu、Huacheng Xu、Pengju Nie、Xiaobo Xie、Zongxiu Nie、Yu Rao

  DOI：10.1002/chem.201304923

  日期：2014.4.1

  A transition‐metal‐free oxidative CN coupling method has been developed for the synthesis of 1H‐azaindazoles and 1H‐indazoles from easily accessible hydrazones. The procedure uses TEMPO, a basic additive, and dioxygen gas as the terminal oxidant. This reaction demonstrates better reactivity, functional group tolerance, and broader scope than comparable metal catalyzed reactions.

  过渡金属-自由氧化Ç  N个耦合方法已为1的合成开发ħ -azaindazoles 1个ħ从容易获得腙-indazoles。该程序使用TEMPO（一种碱性添加剂）和双氧气体作为终端氧化剂。与可比的金属催化反应相比，该反应显示出更好的反应性，官能团耐受性和更宽的范围。
• Trifluoromethyl group in the synthesis of heterocyclic compounds: New and efficient synthesis of 3-aryl-4-aminocinnolines
  作者：Alexander S. Kiselyov

  DOI：10.1016/0040-4039(95)00005-w

  日期：1995.2

  A novel base induced transformation of hydrazones 3a-f derived from trifluoromethylaryl ketones and arylhydrazines was found to produce 3-aryl-4-aminocinnolines 4a-g in 52-75% yield. The initial step of the reaction is believed to involve abstraction of Hf from hydrazone.