((4-(trifluoromethyl)phenyl)ethynyl)magnesium bromide | 1185761-08-3

• 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: ((4-(trifluoromethyl)phenyl)ethynyl)magnesium bromide
• CAS: 1185761-08-3
• 化学式: C₉H₄BrF₃Mg
• 分子量: 273.335
• InChiKey: CCBUZEDEOQLIKG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  ((4-(trifluoromethyl)phenyl)ethynyl)magnesium bromide 在 iron(III) chloride 、 1,2-二碘乙烷 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.33h， 生成 1,4-bis[4-(trifluoromethyl)phenyl]buta-1,3-diyne
  参考文献：
  名称：

  使用鏻离子液体溶剂系统铁催化芳基或炔基格氏试剂的快速均偶联反应

  摘要：

  当反应在鏻盐离子液体溶剂体系中于0℃进行5分钟时，芳基格氏试剂的铁催化均偶联反应很快完成。使用类似的反应体系，也使用离子液体技术完成了炔基格氏试剂的铁催化均偶联反应的第一个例子。© 2011 Wiley Periodicals, Inc. 杂原子化学 22:397–404, 2011; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.20696

  DOI：

  10.1002/hc.20696
• 作为产物：
  描述：

  4-乙炔基-α,α,α-三氟甲苯 在 乙基溴化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 生成 ((4-(trifluoromethyl)phenyl)ethynyl)magnesium bromide
  参考文献：
  名称：

  使用鏻离子液体溶剂系统铁催化芳基或炔基格氏试剂的快速均偶联反应

  摘要：

  当反应在鏻盐离子液体溶剂体系中于0℃进行5分钟时，芳基格氏试剂的铁催化均偶联反应很快完成。使用类似的反应体系，也使用离子液体技术完成了炔基格氏试剂的铁催化均偶联反应的第一个例子。© 2011 Wiley Periodicals, Inc. 杂原子化学 22:397–404, 2011; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.20696

  DOI：

  10.1002/hc.20696

文献信息

• Development of Solvent-Driven Iron-Catalyzed Reactions
  作者：Toshiyuki Itoh

  DOI：10.3987/rev-16-842

  日期：——

  The possibility of solvent-driven iron-catalyzed reactions has been investigated using ionic liquids and acetonitrile as key solvents. Three iron-catalyzed reactions, the intramolecular cyclization of cyclopropane dithioacetals, the [2+2]-cycloaddition of (trans)-anethole, and the [2+3]-type cycloaddition of styrene derivatives with 1,4-benzoquinone, were first developed using acetonitrile as solvent in the presence of 3 similar to 5 mol% of Fe(ClO4)(3)center dot Al2O3 or Fe(BF4)(2)center dot 6H(2)O under air conditions. In particular, we found the rapid cycloaddition of iron-catalyzed [2+3]-type cycloaddition of styrene derivatives with 1,4-benzoquinone when the reaction was carried out in an ionic liquid which contained [PF6] or [Tf2N] anion. Homo-coupling reaction of aryl or alkynyl Grignard reagent was next discovered using 1 mol% of FeCl3 as catalyst and the reaction also proceeded very rapidly in an ionic liquid. We also found that 3-5 mol% of Fe(ClO4)(2)center dot Al2O3 or Fe(BF4)(2)center dot 6H(2)O-successfully catalyzed Friedel-Crafts type alkylation of indoles or pyrroles with vinyl ketones or alpha-aryl-beta-silylalcohol. In particular, the reaction of chiral alpha-aryl-beta-silylalcohol with indole using Fe(ClO4)(3)center dot nH(2)O as catalyst proceeded with retention of the configuration of stereochemistry of the hydroxyl group. Then, we discovered the first example of iron-catalyzed enantioselective C-S bond formation via Michael addition of thiols to (E)-3-crotonoyloxazolidin-2-one using 10 mol% of Fe(BF4)(2)/Pybox. We further demonstrated that Fe(ClO4)(3)center dot Al2O3-catalyzed the Nazarov type cyclizations of thiophene, pyrrole, indole, benzofuran, and benzo[b]thiophene derivatives using ionic liquids as solvent. Solvents have been recognized as a by-player in chemical reactions in the process of "optimization of reaction conditions". However, further investigation of the solvent-driven iron-catalyzed reaction will allow discovery of useful reactions for organic syntheses.
• Synthesis and SAR study of novel pseudo-steroids as potent and selective progesterone receptor antagonists
  作者：Nareshkumar Jain、George Allan、Olivia Linton、Pamela Tannenbaum、Xin Chen、Jun Xu、Peifang Zhu、Joseph Gunnet、Keith Demarest、Scott Lundeen、William Murray、Zhihua Sui

  DOI：10.1016/j.bmcl.2009.01.095

  日期：2009.7

  Synthesis of novel 7-pseudo-steroids 1c has been achieved from trenbolone 3 via an efficient 14 step sequence with overall yields of 10-15%. Various substitutions were incorporated at both the aromatic side chain as well as the D ring. The orientation of aromatic side chain at C10 plays a crucial role for progesterone receptor (PR) activity. Compound 2a (T47D = 1 nM) with -NMe2 para to the aromatic group along with spirofurane groups in the D ring was the optimal substitution. All compounds were also evaluated for glucocorticoid receptor (GR) antagonist activities in vivo in a rat and found efficacious in uterine complement C3 assay via the oral route of administrations. (C) 2009 Elsevier Ltd. All rights reserved.
• Oxidative Homocoupling of Aryl, Alkenyl, and Alkynyl Grignard Reagents with TEMPO and Dioxygen
  作者：Modhu Sudan Maji、Thorben Pfeifer、Armido Studer

  DOI：10.1002/anie.200804197

  日期：2008.11.24
• Gold-Catalyzed Hydroarylation of Aryl Alkynylphosphonates for the Synthesis of Phosphacoumarins
  作者：Cheol-Eui Kim、Taekyu Ryu、Sanghyuck Kim、Kooyeon Lee、Chang-Hee Lee、Phil Ho Lee

  DOI：10.1002/adsc.201300545

  日期：2013.10.11

  AbstractIntramolecular hydroarylation using aryl alkynylphosphonates proceeds smoothly with a gold/silver catalyst in the presence of trifluoromethanesulfonic acid (TfOH) in the 6‐endo mode, thus affording a unique synthetic method for phosphacoumarins having various functional groups, which could be a privileged structure and prevalent scaffold in phosphorus heterocycles.magnified image