1,2-dichloro-4-(3,3,3-trifluoroprop-1-ynyl)benzene | 1356486-29-7

• 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: 1,2-dichloro-4-(3,3,3-trifluoroprop-1-ynyl)benzene
• CAS: 1356486-29-7
• 化学式: C₉H₃Cl₂F₃
• 分子量: 239.024
• InChiKey: NLZOKRXPJBYKQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  1,2-dichloro-4-(3,3,3-trifluoroprop-1-ynyl)benzene 、 氰基甲酸乙酯 在 cobalt(II) iodide 、 锌 、 1,2-双(二环己基磷基)-乙烷 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以24%的产率得到ethyl 4,5-bis(3,4-dichlorophenyl)-3,6-bis(trifluoromethyl)picolinate
  参考文献：
  名称：

  钴催化区域选择性分子间[2+2+2]环加成合成三氟甲基取代的吡啶甲酸乙酯衍生物

  摘要：

  我们展示了芳基-和三氟甲基-取代的内炔和氰基甲酸乙酯的分子间[2+2+2]环加成，并成功地使用CoI 2 /dcype/Zn催化剂体系构建了吡啶衍生物。该反应以高区域选择性进行，并以单一区域异构体的形式获得了两种三氟甲基取代的吡啶甲酸乙酯衍生物。

  DOI：

  10.1055/s-0035-1562432
• 作为产物：
  描述：

  3,3-二甲基-1-(三氟甲基)-1,2-苯并碘氧杂戊环 、 potassium trifluoro((3,4-dichlorophenyl)ethynyl)borate 在 copper(I) thiocyanate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以68%的产率得到1,2-dichloro-4-(3,3,3-trifluoroprop-1-ynyl)benzene
  参考文献：
  名称：

  Synthesis of trifluoromethylated acetylenes via copper-catalyzed trifluoromethylation of alkynyltrifluoroborates

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2012.09.083

文献信息

• An Improved Copper-Mediated Oxidative Trifluoromethylation of Terminal Alkynes
  作者：Ke Zhang、Xiao-Long Qiu、Yangen Huang、Feng-Ling Qing

  DOI：10.1002/ejoc.201101550

  日期：2012.1

  An improved method for the efficient copper-mediated trifluoromethylation of terminal alkynes has been developed. This protocol highlights the convenient access to a variety of aryl-substituted trifluoromethylated alkynes by oxidative trifluoromethylation with two equivalents of TMSCF3 at room temperature.

  已开发出一种用于有效铜介导的末端炔烃三氟甲基化的改进方法。该协议强调了在室温下通过氧化三氟甲基化与两当量的 TMSCF3 方便地获得各种芳基取代的三氟甲基化炔烃。
• Synthesis of trifluoromethyl-group-containing cyclopentadienones by the palladium-catalyzed [2 + 2 + 1] cycloaddition of aryl- and trifluoromethyl-group substituted internal alkynes and carbon monoxide
  作者：Shogo Murakami、Taro Sonehara、Kousuke Iwakami、Hiroaki Tsuji、Motoi Kawatsura

  DOI：10.1016/j.tetlet.2019.01.036

  日期：2019.2

  We investigated the palladium-catalyzed [2 + 2 + 1] cycloaddition of aryl- and trifluoromethyl-group-substituted internal alkynes and carbon monoxide, and revealed that the PdBr2 effectively catalyzed the intended reaction. The PdBr2-catalyzed reaction smoothly proceeded and provided aryl- and trifluoromethyl-group-containing cyclopentadienone derivatives in up to 92% yield.

  我们研究了钯催化的芳基和三氟甲基取代的内部炔烃和一氧化碳的[2 + 2 + 1]环加成反应，并揭示了PdBr 2有效催化了预期的反应。PdBr 2催化的反应顺利进行，并以高达92％的收率提供了含芳基和三氟甲基的环戊二烯酮衍生物。
• 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.
• Synthesis of Trifluoromethyl-Substituted Ethyl Picolinate Derivatives by the Cobalt-Catalyzed Regioselective Intermolecular [2+2+2] Cycloaddition
  作者：Motoi Kawatsura、Tomoki Ishikawa、Taro Sonehara、Shogo Murakami、Maki Minakawa

  DOI：10.1055/s-0035-1562432

  日期：——

  We demonstrated the intermolecular [2+2+2] cycloaddition of aryl- and trifluoromethyl-substituted internal alkyne and ethyl cyano­formate, and succeeded in constructing the pyridine derivatives using the CoI 2 /dcype/Zn catalyst system. The reaction proceeded with a high regioselectivity, and two trifluoromethyl-substituted ethyl picolinate derivatives were obtained as a single regioisomer.

  我们展示了芳基-和三氟甲基-取代的内炔和氰基甲酸乙酯的分子间[2+2+2]环加成，并成功地使用CoI 2 /dcype/Zn催化剂体系构建了吡啶衍生物。该反应以高区域选择性进行，并以单一区域异构体的形式获得了两种三氟甲基取代的吡啶甲酸乙酯衍生物。