2,2,2-trifluoro-1-(3-methoxyphenyl)ethanol | 1375415-94-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,2,2-trifluoro-1-(3-methoxyphenyl)ethanol
• 英文别名: (S)-2,2,2-trifluoro-1-(3-methoxyphenyl)ethanol；(1S)-2,2,2-trifluoro-1-(3-methoxyphenyl)ethan-1-ol；(1S)-2,2,2-trifluoro-1-(3-methoxyphenyl)ethanol
• CAS: 1375415-94-3
• 化学式: C₉H₉F₃O₂
• 分子量: 206.164
• InChiKey: RQAXPSRNKBTNOB-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  trimethyl(2,2,2-trifluoro-1-(3-methoxyphenyl)ethoxy)silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 2,2,2-trifluoro-1-(3-methoxyphenyl)ethanol 、 2,2,2-trifluoro-1-(3-methoxyphenyl)ethanol
  参考文献：
  名称：

  Asymmetric trifluoromethylation of aromatic aldehydes by cooperative catalysis with (IPr)CuF and quinidine-derived quaternary ammonium salt

  摘要：

  已经开发了一种针对醛类的通用对映选择性三氟甲基化反应，使用(IPr)CuF和奎宁衍生的四价铵盐作为协同催化剂。因此，广泛的芳香醛被转化为相应的产物，产率高达92%，对映体过剩率（ee）为81%，催化剂用量为2摩尔百分比。显著增强的活性和对映选择性源于活性[(IPr)CuCF3]的初始生成以及其他铜物种的额外配位活化。

  DOI：

  10.1039/c2ob26827b

文献信息

• The enantioselective trifluoromethylation of aromatic aldehydes by quaternary ammonium bromide and (IPr)CuF at low catalyst loading
  作者：Shaoxiang Wu、Jiyi Guo、Muhammad Sohail、Chengyao Cao、Fu-Xue Chen

  DOI：10.1016/j.jfluchem.2013.01.027

  日期：2013.4

  A general catalytic enantioselective trifluoromethylation of aromatic aldehydes using (IPr)CuF and quinidine-derived quaternary ammonium salt as catalysts has been developed. A wide range of aromatic aldehydes are converted to the corresponding products in up to 92% yield and 81% ee at 2 mol% of catalyst loading. (C) 2013 Elsevier B.V. All rights reserved.
• Cinchona alkaloid/TMAF combination: Enantioselective trifluoromethylation of aryl aldehydes
  作者：Hiroyuki Kawai、Satoshi Mizuta、Etsuko Tokunaga、Norio Shibata

  DOI：10.1016/j.jfluchem.2013.01.032

  日期：2013.8

  The catalytic enantioselective trifluoromethylation reaction of aromatic aldehydes using the Ruppert-Prakash reagent (Me3SiCF3) has been disclosed, with an operationally simple procedure, based on the combination of sterically demanding cinchona alkaloid-derived phase-transfer catalyst 3b with tetramethylammonium fluoride (TMAF). Our methodology provides medicinally important alpha-trifluoromethyl alcohols with high chemical yields and moderate to good enantioselectivities (50-70% ee). (c) 2013 Elsevier B.V. All rights reserved.
• Asymmetric trifluoromethylation of aromatic aldehydes by cooperative catalysis with (IPr)CuF and quinidine-derived quaternary ammonium salt
  作者：Shaoxiang Wu、Wei Zeng、Qi Wang、Fu-Xue Chen

  DOI：10.1039/c2ob26827b

  日期：——

  A general enantioselective trifluoromethylation of aldehydes has been developed using (IPr)CuF and quinidine-derived quaternary ammonium salt as the cooperative catalyst. Thus, a wide range of aromatic aldehydes have been converted to the corresponding products in up to 92% yield and 81% ee at 2 mol% of catalyst loading. The greatly enhanced activity and enantioselectivity result from the initiative generation of active [(IPr)CuCF3] as well as additional coordination activation of other copper species.

  已经开发了一种针对醛类的通用对映选择性三氟甲基化反应，使用(IPr)CuF和奎宁衍生的四价铵盐作为协同催化剂。因此，广泛的芳香醛被转化为相应的产物，产率高达92%，对映体过剩率（ee）为81%，催化剂用量为2摩尔百分比。显著增强的活性和对映选择性源于活性[(IPr)CuCF3]的初始生成以及其他铜物种的额外配位活化。