4-(2,2,2-trifluoro-1-(4-methoxyphenyl)ethyl)phenol | 1443226-05-8

• 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-(2,2,2-trifluoro-1-(4-methoxyphenyl)ethyl)phenol
• 英文别名: 4-[2,2,2-Trifluoro-1-(4-methoxyphenyl)ethyl]phenol
• CAS: 1443226-05-8
• 化学式: C₁₅H₁₃F₃O₂
• 分子量: 282.262
• InChiKey: RNMLUPMJBUKJTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  碘乙烷 、 4-(2,2,2-trifluoro-1-(4-methoxyphenyl)ethyl)phenol 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 以89 %的产率得到
  参考文献：
  名称：

  1,6-Nucleophilic Di- and Trifluoromethylation of para-Quinone Methides with Me3SiCF2H/Me3SiCF3 Facilitated by CsF/18-Crown-6

  摘要：

  The direct 1,6-nucleophilic difluoromethylation, trifluoromethylation, and difluoroalkylation of para-quinone methides (p-QMs) with Me3SiRf (Rf = CF2H, CF3, CF2CF3, CF2COOEt, and CF2SPh) under mild conditions are described. Although Me3SiCF2H shows lower reactivity than Me3SiCF3, it can react with p-QMs promoted by CsF/18-Crown-6 to give structurally diverse difluoromethyl products in good yields. The products can then be further converted into fluoroalkylated para-quinone methides and α-fluoroalkylated diarylmethanes.

  DOI：

  10.3390/molecules29122905
• 作为产物：
  描述：

  2,6-di-tert-butyl-4-(2,2,2-trifluoro-1-(4-methoxyphenyl)ethyl)phenol 在 硫酸 作用下， 以 甲苯 为溶剂， 以75 %的产率得到4-(2,2,2-trifluoro-1-(4-methoxyphenyl)ethyl)phenol
  参考文献：
  名称：

  1,6-Nucleophilic Di- and Trifluoromethylation of para-Quinone Methides with Me3SiCF2H/Me3SiCF3 Facilitated by CsF/18-Crown-6

  摘要：

  The direct 1,6-nucleophilic difluoromethylation, trifluoromethylation, and difluoroalkylation of para-quinone methides (p-QMs) with Me3SiRf (Rf = CF2H, CF3, CF2CF3, CF2COOEt, and CF2SPh) under mild conditions are described. Although Me3SiCF2H shows lower reactivity than Me3SiCF3, it can react with p-QMs promoted by CsF/18-Crown-6 to give structurally diverse difluoromethyl products in good yields. The products can then be further converted into fluoroalkylated para-quinone methides and α-fluoroalkylated diarylmethanes.

  DOI：

  10.3390/molecules29122905

文献信息

• Photoactivation of (<i>p</i>-Methoxyphenyl)(trifluoromethyl)diazirine in the Presence of Phenolic Reaction Partners
  作者：Björn Raimer、Thomas Lindel

  DOI：10.1002/chem.201203479

  日期：2013.5.17

  Shine light on your chemistry! Irradiating 3‐(4‐methoxyphenyl)‐3‐(trifluoromethyl)‐3H‐diazirine in the presence of equimolar solutions of phenol and tyrosine derivatives leads to Friedel–Crafts alkylations (see scheme), which suggests a strategy for the development of “cleaner” diazirines for chemical biology.

  照亮您的化学物质！在苯酚和酪氨酸衍生物等摩尔溶液的存在下辐射3-（4-甲氧基苯基）-3-（三氟甲基）-3 H-二氮嗪可导致弗瑞德-克拉夫茨烷基化反应（参见方案），这为开发“化学生物学的“更清洁”二嗪类。
• Cross-dehydrogenative coupling enables enantioselective access to CF₃-substituted all-carbon quaternary stereocenters
  作者：Xiaoguang Pan、Zehua Wang、Linglong Kan、Ying Mao、Yasheng Zhu、Lei Liu

  DOI：10.1039/c9sc05894j

  日期：——

  strategy for enantioselective access to acyclic CF3-substituted all-carbon quaternary stereocenters has been established. By using catalytic DDQ with MnO2 as an inexpensive terminal oxidant, asymmetric cross coupling of racemic δ-CF3-substituted phenols with indoles proceeded smoothly, providing CF3-bearing all-carbon quaternary stereocenters with excellent chemo- and enantioselectivities. The generality

  已经建立了对映选择性进入无环CF 3取代的全碳四元立体中心的交叉脱氢偶联策略。通过使用催化DDQ用的MnO 2作为一种廉价的终端氧化剂，外消旋δ-CF的非对称交叉偶联3与吲哚取代的酚顺利，提供CF 3荷瘤的全碳季立体具有优良的化疗和对映选择性。通过有效构建带有其他多氟烷基和全氟烷基（例如CF 2 Cl，C 2 F 5和C 3 F）的全碳四元立体中心，进一步证明了该策略的普遍性7。
• Quantum chemical calculation of 19F NMR chemical shifts of trifluoromethyl diazirine photoproducts and precursors
  作者：Björn Raimer、Peter G. Jones、Thomas Lindel

  DOI：10.1016/j.jfluchem.2014.06.027

  日期：2014.10

  Irradiation of aryl(trifluoromethyl)diazirines may result in a multitude of products, which are difficult to assign in the F-19 NMR spectrum. In this article, it is demonstrated that an average accuracy of 2.9 ppm (standard deviation) can be achieved by quantum chemical calculations at the B3LYP 6-311G++(2d,2p) level of theory, followed by a Boltzmann weighting of the optimized conformers. A set of 30 compounds was investigated both-experimentally and theoretically. F-19 NMR chemical shifts of precursor Z-oximes and Z-tosyloximes ranged from delta(F) -62.9 to -61.8 ppm, whereas their E counterparts showed shifts between delta(F) -67.2 and -66.2 ppm. Stereochemical assignments were confirmed by two X-ray analyses. Quantum chemical calculation also allowed the assignment of the configuration of an (E,E) azine. Trifluoromethyl diazirines exhibited a delta(F) between -66.1 and -65.6, diaziridines between -76.2 and -75.9 ppm. The smallest delta(F) values were observed for alpha-oxygenated trifluoromethyl compounds (delta(F) -78.9 to -77.4 ppm). The average deviation of the calculated from the experimental values corresponds to only about 1% of the standard F-19 NMR chemical shift range. (C) 2014 Elsevier B.V. All rights reserved.