2-phenoxy-1-(4-(trifluoromethyl)phenyl)ethan-1-one | 166189-99-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-phenoxy-1-(4-(trifluoromethyl)phenyl)ethan-1-one
• 英文别名: 2-Phenoxy-1-(4-trifluoromethyl-phenyl)-ethanone；2-phenoxy-1-[4-(trifluoromethyl)phenyl]ethanone
• CAS: 166189-99-7
• 化学式: C₁₅H₁₁F₃O₂
• 分子量: 280.246
• InChiKey: PGENCEKUWRSLRQ-UHFFFAOYSA-N

物化性质

• 沸点：
  381.4±42.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-phenoxy-1-(4-(trifluoromethyl)phenyl)ethan-1-one 在 氯化铵 、 锌 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以74%的产率得到4'-三氟甲基苯乙酮
  参考文献：
  名称：

  芳基丙烯酰基O-烷基和O-苯基衍生物转化为酮

  摘要：

  摘要 在乙醇中用 2-3 当量 Zn 和 1-2 当量 NH4Cl 处理芳基酰（α-羟基酮）O-烷基和 O-苯基衍生物，回流 20-120 分钟，得到相应的酮，收率极好. 此外，α,β-环氧酮可以有效地转化为β-羟基酮，2,2-二烷氧基-1-苯基酮也可以脱烷氧基化为1-苯基酮。

  DOI：

  10.1080/00397910600978564
• 作为产物：
  描述：

  2-溴-4'-(三氟甲基)苯乙酮 、 苯酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-phenoxy-1-(4-(trifluoromethyl)phenyl)ethan-1-one
  参考文献：
  名称：

  美西美汀及其类似物在冠醚基手性固定相上的液相色谱拆分

  摘要：

  一种有效的IB类抗心律失常药美西律及其类似物在三种基于冠醚的手性固定相（CSP）上分离，其中一种（CSP 1）基于（+）-（18-crown-6）- 2,3,11,12-四羧酸和另外两种（CSP 2和CSP 3）基于（3,3'-diphenyl-1,1'-binaphthyl）-20-crown-6。美西律汀在CSP 1和CSP 3上的拆分度（R S）大于1.00，在二氧化硅表面上含有残留的保护硅烷醇基团的正辛基，但在CSP 2上的拆分度（R S）小于1.00。在三种CSP的手性中心拆分含美西律汀类似物的色谱行为，在很大程度上取决于分析物的苯氧基。即，即使手性识别效率随CSP的不同而不同，包含2,6-二甲基苯氧基，3,4-二甲基苯氧基，3-甲基苯氧基，4-甲基苯氧基和简单的苯氧基的美西律类似物在三个CSP上也能很好地拆分。但是，含2-甲基苯氧基的美西律类似物根本不被溶解或仅被轻微溶解。在这三种CSP中，发现CSP

  DOI：

  10.1002/chir.22318

文献信息

• Transformation of Aryl Acyloin <i>O</i>‐Alkyl and <i>O</i>‐Phenyl Derivatives to Ketones
  作者：Zhiyi Yao、Deju Ye、Hong Liu、Kaixian Chen、Hualiang Jiang

  DOI：10.1080/00397910600978564

  日期：2007.1.1

  aryl acyloin (α‐hydroxyketone) O‐alkyl and O‐phenyl derivatives with 2–3 equiv of Zn and 1–2 equiv of NH4Cl in ethanol, refluxing for 20–120 min, gave the corresponding ketones with excellent yields. Further, α,β‐epoxy ketones can be efficiently transformed to β‐hydroxy ketones, and 2,2‐dialkoxy‐1‐phenyl ketone also can be dealkoxylated to 1‐phenyl ketone.

  摘要 在乙醇中用 2-3 当量 Zn 和 1-2 当量 NH4Cl 处理芳基酰（α-羟基酮）O-烷基和 O-苯基衍生物，回流 20-120 分钟，得到相应的酮，收率极好. 此外，α,β-环氧酮可以有效地转化为β-羟基酮，2,2-二烷氧基-1-苯基酮也可以脱烷氧基化为1-苯基酮。
• Liquid Chromatographic Resolution of Mexiletine and Its Analogs on Crown Ether-Based Chiral Stationary Phases
  作者：Kab Bong Jin、Hee Eun Kim、Myung Ho Hyun

  DOI：10.1002/chir.22318

  日期：2014.5

  effective class IB antiarrhythmic agent, and its analogs were resolved on three different crown ether‐based chiral stationary phases (CSPs), one (CSP 1) of which is based on (+)‐(18‐crown‐6)‐2,3,11,12‐tetracarboxylic acid and the other two (CSP 2 and CSP 3) are based on (3,3’‐diphenyl‐1,1’‐binaphthyl)‐20‐crown‐6. Mexiletine was resolved with a resolution (RS) of greater than 1.00 on CSP 1 and CSP 3

  一种有效的IB类抗心律失常药美西律及其类似物在三种基于冠醚的手性固定相（CSP）上分离，其中一种（CSP 1）基于（+）-（18-crown-6）- 2,3,11,12-四羧酸和另外两种（CSP 2和CSP 3）基于（3,3'-diphenyl-1,1'-binaphthyl）-20-crown-6。美西律汀在CSP 1和CSP 3上的拆分度（R S）大于1.00，在二氧化硅表面上含有残留的保护硅烷醇基团的正辛基，但在CSP 2上的拆分度（R S）小于1.00。在三种CSP的手性中心拆分含美西律汀类似物的色谱行为，在很大程度上取决于分析物的苯氧基。即，即使手性识别效率随CSP的不同而不同，包含2,6-二甲基苯氧基，3,4-二甲基苯氧基，3-甲基苯氧基，4-甲基苯氧基和简单的苯氧基的美西律类似物在三个CSP上也能很好地拆分。但是，含2-甲基苯氧基的美西律类似物根本不被溶解或仅被轻微溶解。在这三种CSP中，发现CSP
• Photochemical Generation of Radical Anions of Photolabile Aryl Ketones
  作者：N. Mathivanan、L. J. Johnston、D. D. M. Wayner

  DOI：10.1021/j100020a048

  日期：1995.5

  The radical anions of a series of substituted alpha-(aryloxy)acetophenones have been generated by trapping the solvated electron produced by 355-nm laser-induced photoionization of 4,4'-dimethoxystilbene in either acetonitrile or dimethylformamide (DMF). The radical anion of the parent ketone, alpha-phenoxyacetophenone, has lambda(max) at 500 nm and decays with a rate constant 7 x 10(5) s(-1). This rate constant reflects the rate of beta-cleavage to generate phenoxide ion and phenacyl radical. The rate constant for beta-cleavage decreases for ketones with electron donating substituents in the alpha-aryloxy ring. Substituent effects on the aceotphenone ring are in the opposite direction, and many of the 4-substituted (aryloxy)acetophenones have half-lives in excess of 10 mu s that reflect a combination of second order processes and are not limited by beta-cleavage. The generality of the photoionization/electron trapping method for the generation of radical anions of ketones with short-lived excited states that preclude direct excitation is illustrated by its application to other aryl ketones that undergo alpha-cleavage, beta-phenyl quenching, and intramolecular hydrogen abstraction reactions.
• Electrochemistry of Electron Transfer Probes. Observation of the Transition from Activation to Counterdiffusion Control in the Fragmentation of α-Aryloxyacetophenone Radical Anions¹^a
  作者：Mogens L. Andersen、William Long、Danial D. M. Wayner

  DOI：10.1021/ja963374u

  日期：1997.7.1

  The cleavage of radical anions of substituted alpha-phenoxyacetophenones, X-C6H4COCH2OPh, IIa-k, has been studied in DMF by voltammetric and coulometric techniques. The standard potentials (E degrees) for formation of and rate constants, k, for the cleavage of the radical anions were determined using linear sweep voltammetry, LSV, together with digital simulation and previously reported laser flash photolysis data. The rate constants cover a range of almost eight orders of magnitude (0.4 s(-1) for X = p-MeCO- to 1.3.10(7) s(-1) for X = p-MeO-). The relative driving forces, Delta Delta G degrees(het)(RX.-), for the heterolytic cleavage of the radical anions (to give R-. + X-) were estimated from thermochemical cycles. A combined plot of log(k) versus Delta Delta G(het)degrees(RX.-) for the radical anions of IIa-k and of alpha-aryloxyacetophenones gave a curve with alpha = 0.5 at high driving forces and alpha = 1 at low driving forces, where alpha = partial derivative Delta G(0)(double dagger)/partial derivative Delta G degrees. The plot was analyzed using a model in which reversible cleavage of the radical anions takes place inside the solvent cage followed by (counter)diffusion of the fragments out of the solvent cage. The change in the value of a is interpreted as a change in the rate limiting process from chemical activation (i.e.,, fragmentation) to counterdiffusion. The model allowed the determination of the absolute values of Delta G(het)degrees(RX.-) and the intrinsic barrier, Delta G(0)(double dagger), for the fragmentation of the radical anions (8 +/- 1 kcal mol(-1), 0.35 eV). This leads to an estimate of the homolytic bond dissociation free energy of the C-OPh bond in the unsubstituted alpha-phenoxyacetophenone.
• Cobalt-Catalyzed Reductive C–O Bond Cleavage of Lignin β-O-4 Ketone Models via In Situ Generation of the Cobalt–Boryl Species
  作者：Kecheng Gao、Man Xu、Cheng Cai、Yanghao Ding、Jianhui Chen、Bosheng Liu、Yuanzhi Xia

  DOI：10.1021/acs.orglett.0c02117

  日期：2020.8.7

  An efficient and mild method for reductive C–O bond cleavage of lignin β-O-4 ketone models was developed to afford the corresponding ketones and phenols with PDI-CoCl2 as the precatalyst and diboron reagent as the reductant. The synthetic utility of the methodology was demonstrated by depolymerization of a polymeric model and gram-scale transformation. Mechanistic studies suggested that this transformation

  开发了一种有效且温和的方法来还原木质素β-O-4酮模型的C-O键断裂，以PDI -CoCl 2为前催化剂和以二硼试剂为还原剂提供相应的酮和苯酚。该方法的合成效用通过聚合物模型的解聚和克级转化得以证明。机理研究表明，这种转化涉及羰基插入，1,2-布鲁克型重排，β-氧消除和催化活性Co-B物种限速再生的步骤。