9-(3,3,3-trifluoroprop-1-yn-1-yl)phenanthrene | 1361988-17-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 9-(3,3,3-trifluoroprop-1-yn-1-yl)phenanthrene
• 英文别名: 9-(3,3,3-trifluoroprop-1-ynyl)phenanthrene；9-(3,3,3-Trifluoroprop-1-ynyl)phenanthrene
• CAS: 1361988-17-1
• 化学式: C₁₇H₉F₃
• 分子量: 270.254
• InChiKey: PNGLLBOXNBNLBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  9-(3,3,3-trifluoroprop-1-yn-1-yl)phenanthrene 、 trifluoromethylcopper(I) 在 联硼酸频那醇酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以70%的产率得到9-(3,3,3-trifluoro-2-(trifluoromethyl)prop-1-en-1-yl)phenanthrene
  参考文献：
  名称：

  Domino Hydroboration/Trifluoromethylation of Alkynes Using Fluoroform-Derived [CuCF₃]

  摘要：

  A domino hydroboration/trifluoromethylation (formal hydrotrifluoromethylation) of alkynes using the fluoroform-derived [CuCF3] reagent is achieved. Synthetically useful (E)-alkenyl-CF3 building blocks and 1,1-bis(trifluoromethyl)-substituted alkenes can be prepared under ambient conditions in one pot/one step from alkynes. The ultimate source of CF3 is the inexpensive industrial waste fluoroform.

  DOI：

  10.1021/acs.joc.7b00755
• 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 、 9-乙炔基菲 在 copper(l) iodide 、 1,10-菲罗啉 、 potassium hydrogencarbonate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以91%的产率得到9-(3,3,3-trifluoroprop-1-yn-1-yl)phenanthrene
  参考文献：
  名称：

  使用亲电子三氟甲基化试剂进行轻度铜催化的末端炔烃三氟甲基化

  摘要：

  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。

  DOI：

  10.1016/j.tet.2011.12.085

文献信息

• Fluoroform-Derived CuCF₃ for Trifluoromethylation of Terminal and TMS-Protected Alkynes
  作者：Lisi He、Gavin Chit Tsui

  DOI：10.1021/acs.orglett.6b00999

  日期：2016.6.17

  An efficient trifluoromethylation reaction of alkynes using a fluoroform-derived CuCF3 reagent is described. The CF3 source is the inexpensive industrial waste fluoroform (CF3H). The air-stable CuCF3 reagent can be prepared in large quantities and is convenient to use. Synthetically useful trifluoromethylated alkynes containing a wide range of functional groups were successfully synthesized under mild conditions. Both terminal and TMS-protected alkynes gave the products in one step. The beneficial effect of a diamine ligand tetramethylethylenediamine (TMEDA) with the fluoroform-derived CuCF3 reagent was also demonstrated.
• 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。
• Domino Hydroboration/Trifluoromethylation of Alkynes Using Fluoroform-Derived [CuCF₃]
  作者：Lisi He、Xinkan Yang、Gavin Chit Tsui

  DOI：10.1021/acs.joc.7b00755

  日期：2017.6.16

  A domino hydroboration/trifluoromethylation (formal hydrotrifluoromethylation) of alkynes using the fluoroform-derived [CuCF3] reagent is achieved. Synthetically useful (E)-alkenyl-CF3 building blocks and 1,1-bis(trifluoromethyl)-substituted alkenes can be prepared under ambient conditions in one pot/one step from alkynes. The ultimate source of CF3 is the inexpensive industrial waste fluoroform.