1-propyl-4-(3,3,3-trifluoroprop-1-yn-1-yl)benzene | 127300-01-0

• 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: 1-propyl-4-(3,3,3-trifluoroprop-1-yn-1-yl)benzene
• 英文别名: 1-propyl-4-(3,3,3-trifluoroprop-1-ynyl)benzene
• CAS: 127300-01-0
• 化学式: C₁₂H₁₁F₃
• 分子量: 212.215
• InChiKey: LHHYJJGLMHZZTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 1-propyl-4-(3,3,3-trifluoroprop-1-yn-1-yl)benzene 、 白碳黑 生成 4-(4-propylphenyl)-3-(trifluoromethyl)phenol
  参考文献：
  名称：

  HIYAMA, TAMEJIRO;SATO, KEN-ICHI, SYNLETT.,(1990) N, C. 53-59

  摘要：

  DOI：
• 作为产物：
  描述：

  4-丙基苯乙炔 在 叔丁基过氧化氢 、 正丁基锂 、 碳酸氢钠 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 1-propyl-4-(3,3,3-trifluoroprop-1-yn-1-yl)benzene
  参考文献：
  名称：

  Copper-mediated trifluoromethylation of potassium alkynyltrifluoroborates with Langlois' reagent

  摘要：

  Synthesis of trifluoromethylated acetylenes by copper-mediated trifluoromethylation of potassium alkynyltrifluoroborates with CF3 radicals generated from NaSO2CF3 and tert-butyl hydroperoxide (TBHP) is communicated. The trifluoromethylated acetylenes were obtained in good to moderate yields. The presented method tolerates a wide range of aromatic, heteroaromatic, and aliphatic potassium alkynyltrifluoroborates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.005

文献信息

• Copper-Mediated Aerobic Oxidative Trifluoromethylation of Terminal Alkynes with Me₃SiCF₃
  作者：Lingling Chu、Feng-Ling Qing

  DOI：10.1021/ja102175w

  日期：2010.6.2

  An efficient copper-mediated trifluoromethylation of terminal alkynes with nucleophilic trifluoromethylating reagent (Me(3)SiCF(3)) was developed. Both aromatic alkynes and aliphatic alkynes were effective, and a variety of functionalities such as amino, -OMe, -CO(2)Et, -Br, and -NO(2) were tolerated under the reaction conditions. This reaction provides a general, straightforward, and practically useful

  开发了一种有效的铜介导的末端炔烃与亲核三氟甲基化试剂 (Me(3)SiCF(3)) 的三氟甲基化。芳香族炔烃和脂肪族炔烃都是有效的，并且在反应条件下可以容忍各种官能团，例如氨基、-OMe、-CO(2)Et、-Br 和-NO(2)。该反应为制备三氟甲基化乙炔提供了一种通用、直接且实用的方法。
• Mild copper-catalyzed trifluoromethylation of terminal alkynes using an electrophilic trifluoromethylating reagent
  作者：Zhiqiang Weng、Huaifeng Li、Weiming He、Liang-Feng Yao、Jianwei Tan、Jinfa Chen、Yaofeng Yuan、Kuo-Wei Huang

  DOI：10.1016/j.tet.2011.12.085

  日期：2012.3

  A catalytic process for trifluoromethylation of terminal alkynes with Togni’s reagent has been developed, affording trifluoromethylated acetylenes in good to excellent yields. The reaction is conducted at room temperature and exhibits tolerance to a range of functional groups.

  已经开发出用Togni试剂催化末端炔烃的三氟甲基化的催化方法，从而以良好或优异的收率提供了三氟甲基化的乙炔。该反应在室温下进行，并且表现出对一定范围的官能团的耐受性。
• Copper-Mediated Trifluoromethylation of Terminal Alkynes by<i>S</i>-(Trifluoromethyl)diarylsulfonium Salt
  作者：Xiaoping Wang、Jinhong Lin、Chengpan Zhang、Jichang Xiao、Xing Zheng

  DOI：10.1002/cjoc.201300393

  日期：2013.7

  The copper‐mediated trifluoromethylation of terminal alkynes with S‐(trifluoromethyl)diarylsulfonium salt has been carefully investigated. The reactions proceeded smoothly to afford trifluoromethylated acetylenes in moderate to good yields. This approach is a convenient method to synthesize a variety of functional trifluoromethylated acetylenes.

  仔细研究了末端炔烃与S-（三氟甲基）二芳基ulf盐的铜介导的三氟甲基化。反应进行顺利，以中等至良好的产率得到三氟甲基化的乙炔。这种方法是合成各种功能性三氟甲基化乙炔的简便方法。
• Synthesis of trifluoromethylated acetylenes via copper-catalyzed trifluoromethylation of alkynyltrifluoroborates
  作者：Huidong Zheng、Yuanyuan Huang、Zhiwei Wang、Huaifeng Li、Kuo-Wei Huang、Yaofeng Yuan、Zhiqiang Weng

  DOI：10.1016/j.tetlet.2012.09.083

  日期：2012.12

  A new method for the synthesis of trifluoromethylated acetylenes is developed which involves the copper-catalyzed trifluoromethylation of alkynyltrifluoroborates with an electrophilic trifluoromethylating reagent. This method offers significant advantages such as efficiency and mild and base-free reaction conditions. A plausible mechanism is proposed. (c) 2012 Published by Elsevier Ltd.