5-(trifluoromethyl)-2-vinylphenol | 1510865-24-3

• 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: 5-(trifluoromethyl)-2-vinylphenol
• 英文别名: 2-Ethenyl-5-(trifluoromethyl)phenol
• CAS: 1510865-24-3
• 化学式: C₉H₇F₃O
• 分子量: 188.149
• InChiKey: BFQSNPMJVHFMRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二苯基乙炔 、 5-(trifluoromethyl)-2-vinylphenol 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper(II) acetate monohydrate 作用下， 以 乙腈 为溶剂， 以86%的产率得到2,3-diphenyl-8-(trifluoromethyl)benzo[b]oxepine
  参考文献：
  名称：

  Straightforward Assembly of Benzoxepines by Means of a Rhodium(III)-Catalyzed C–H Functionalization of o-Vinylphenols

  摘要：

  Readily available o-vinylphenols undergo a formal (5 + 2) cycloaddition to alkynes when treated with catalytic amounts of [Cp*RhCl2](2) and Cu(OAc)(2). The reaction, which involves the cleavage of the terminal C-H bond of the alkenyl moiety, generates highly valuable benzoxepine skeletons in a practical, versatile, and atom-economical manner. Using carbon monoxide instead of an alkyne as reaction partner leads to coumarin products which formally result from a (5 + 1) cycloaddition.

  DOI：

  10.1021/ja410538w
• 作为产物：
  描述：

  2-methoxy-4-(trifluoromethyl)-1-vinylbenzene 在 potassium tert-butylate 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 生成 5-(trifluoromethyl)-2-vinylphenol
  参考文献：
  名称：

  Straightforward Assembly of Benzoxepines by Means of a Rhodium(III)-Catalyzed C–H Functionalization of o-Vinylphenols

  摘要：

  Readily available o-vinylphenols undergo a formal (5 + 2) cycloaddition to alkynes when treated with catalytic amounts of [Cp*RhCl2](2) and Cu(OAc)(2). The reaction, which involves the cleavage of the terminal C-H bond of the alkenyl moiety, generates highly valuable benzoxepine skeletons in a practical, versatile, and atom-economical manner. Using carbon monoxide instead of an alkyne as reaction partner leads to coumarin products which formally result from a (5 + 1) cycloaddition.

  DOI：

  10.1021/ja410538w

文献信息

• <i>Ortho</i>-Vinylation Reaction of Phenols with Ethyne
  作者：Masahiko Yamaguchi、Mieko Arisawa、Kenji Omata、Kuninobu Kabuto、Masahiro Hirama、Tadafumi Uchimaru

  DOI：10.1021/jo980785f

  日期：1998.10.1

  Phenols were vinylated at the ortho-position with ethyne in the presence of SnCl(4)-Bu(3)N reagent. The reaction was applicable to phenols possessing either electron-donating or electron-withdrawing groups. 2,6-Divinylphenols were synthesized under modified conditions. A reaction mechanism involving carbostannylation of alkynyltin and phenoxytin was discussed.

  在SnCl（4）-Bu（3）N试剂存在的情况下，在乙炔的邻位乙烯基化乙烯基苯酚。该反应适用于具有给电子或吸电子基团的酚。在改性条件下合成了2，6-二乙烯基苯酚。讨论了炔基锡和苯氧基锡的羰基化反应的反应机理。