2,2,2-trifluoro-1-(o-tolyl)ethanol | 438-24-4

• 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: 2,2,2-trifluoro-1-(o-tolyl)ethanol
• 英文别名: 2,2,2-trifluoro-1-(2-methylphenyl)ethanol
• CAS: 438-24-4
• 化学式: C₉H₉F₃O
• mdl: MFCD00544591
• 分子量: 190.165
• InChiKey: SXMWJABIUDHACE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2903999090
• 储存条件：
  存储条件：2-8°C，密封保存，置于干燥处。

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoro-1-(o-tolyl)ethanol 在 palladium on activated charcoal sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 2-硝基丙烷 、 氢气 、 sodium ethanolate 、 sodium hydride 、 过氧化苯甲酰 作用下， 以 1,4-二氧六环 、 甲醇 、 四氯化碳 、 乙醚 、 乙醇 为溶剂， 反应 18.0h， 生成 <2-(2,2,2-Trifluoroethyl)phenyl>diazomethane
  参考文献：
  名称：

  Intramolecular Reactivity of Arylcarbenes: Derivatives of o-Tolylcarbene

  摘要：

  Various CH(2)X groups have been attached to the ortho position of phenylcarbene. If 2'- or 3'-C-H bonds are present, as in 23 (X = Me), 71 (X = CMe(3)), and 58 (X = SiMe(3)), C-H insertion leading to five- or six-membered rings predominates in the gas phase and competes with intermolecular reactions in solution. The formation of benzocyclobutenes via insertion into 1'-C-H bonds is a very minor reaction path of 23 and 71. In contrast, 58 produces substantial amounts of the benzocyclobutene 59 by way of C-Si insertion, particularly in the gas phase. Insertion into the Si-Me bonds of 58 also occurs while the C-F bonds of 37 (X = CF3) and 50 (X = Fl are inert. In the gas phase, 37 and 50 give mainly benzocyclobutenes whereas intermolecular reactions prevail in solution. The effects of sensitization and of solvent polarity suggest that benzocyclobutenes arise from singlet arylcarbenes. The amount of carbene-carbene rearrangement decreases in the order 7 (X = H) > 37 (X = CF3) > 23 (X = Me); no rearrangement was observed with 50 (X = Fl, 58 (X = SiMe(3)), and 71 (X = CMe(3)).

  DOI：

  10.1021/jo00093a014
• 作为产物：
  描述：

  2'-甲基-2,2,2-三氟苯乙酮 在 三丁基膦 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以71%的产率得到2,2,2-trifluoro-1-(o-tolyl)ethanol
  参考文献：
  名称：

  Reduction of 2,2,2-trifluoro-1-arylethanones with alkyl phosphines

  摘要：

  In the presence of alkyl phosphines, reduction of 2,2,2-trifluoro-1-arylethanones proceeded smoothly to give the corresponding reduction products in moderate to high yields at room temperature. The possible mechanism was discussed on the basis of deuterium labeling and control experiments, indicating that one hydrogen transfer took place from alkyl phosphine to the carbonyl group activated by a strongly electron-withdrawing trifluoromethyl group. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.09.084

文献信息

• Nonenzymatic kinetic resolution of racemic 2,2,2-trifluoro-1-aryl ethanol via enantioselective acylation
  作者：Qing Xu、Hui Zhou、Xiaohong Geng、Peiran Chen

  DOI：10.1016/j.tet.2009.01.058

  日期：2009.3

  Kinetic resolution of a series of 2,2,2-trifluoro-1-aryl ethanol with (R)-benzotetramisole as the catalyst has been investigated. The result showed that when the aryl group in the substrate was a phenyl (or a phenyl substituted by an electron-donating group) or a naphthyl (an extended phenyl) group, the system could give an s value higher than 20. Preparative KR examples demonstrated the applicability

  研究了一系列以（R）-苯并四咪唑为催化剂的2,2,2-三氟-1-芳基乙醇的动力学拆分。结果表明，当底物中的芳基为苯基（或被供电子基团取代的苯基）或萘基（延伸的苯基）时，该体系的s值可大于20。制备KR实例证明该方法在制备一些对映体纯的2,2,2-三氟-1-芳基乙醇或2,2,2-三氟-1-芳基-乙基异丁酸酯中的适用性。
• [EN] INHIBITORS OF ADENYLATE-FORMING ENZYME MENE<br/>[FR] INHIBITEURS DE L'ENZYME MENE FORMANT L'ADÉNYLATE CYCLASE
  申请人：MEMORIAL SLOAN KETTERING CANCER CENTER

  公开号：WO2020163673A1

  公开（公告）日：2020-08-13

  Provided herein are compounds of Formula (I) and pharmaceutically acceptable salts or tautomers thereof which may inhibit adenylate-forming enzymes. Also provided are pharmaceutical compositions, kits, uses, and methods involving the inventive compounds for the treatment and/or prevention of an infectious disease (e.g., bacterial infection (e.g., tuberculosis, methicillin- resistant Staphylococcus aureus)).

  本文提供了式（I）的化合物及其药用可接受的盐或互变异构体，这些化合物可能抑制腺苷酸形成酶。还提供了涉及这些创新化合物用于治疗和/或预防传染病（例如细菌感染（例如结核病、耐甲氧西林金黄色葡萄球菌））的药物组合物、试剂盒、用途和方法。
• Synthesis of Perfluoroalkyl-Substituted Vinylcyclopropanes by Way of Enhanced Neighboring Group Participation
  作者：Christopher B. Kelly、Michael A. Mercadante、Emma R. Carnaghan、Matthew J. Doherty、Diana C. Fager、John J. Hauck、Allyson E. MacInnis、Leon J. Tilley、Nicholas E. Leadbeater

  DOI：10.1002/ejoc.201500565

  日期：2015.7

  homoallyl alcohols is disclosed. Destabilization of the cationic intermediate by the electron-withdrawing CF3 group greatly enhances neighboring group participation of the alkene, allowing ring closure to predominate. The reaction can be extended to the difluoromethyl and pentafluoroethyl group, enabling the preparation of a diverse array of fluoroalkyl-substituted vinylcyclopropanes.

  公开了一种用于从 α-CF3 高烯丙醇制备三氟甲基取代的乙烯基环丙烷的简单、高产、两步、一锅法。吸电子 CF3 基团对阳离子中间体的不稳定极大地增强了烯烃的相邻基团参与，从而使闭环占主导地位。该反应可以扩展到二氟甲基和五氟乙基，从而能够制备多种氟代烷基取代的乙烯基环丙烷。
• Nucleophilic Trifluoromethylation of Carbonyl Compounds: Trifluoroacetaldehyde Hydrate as a Trifluoromethyl Source
  作者：G. K. Surya Prakash、Zhe Zhang、Fang Wang、Socrates Munoz、George A. Olah

  DOI：10.1021/jo400202w

  日期：2013.4.5

  feasible nucleophilic trifluoromethylating protocol has been developed using trifluoroacetaldehyde hydrate as an atom-economical trifluoromethyl source. The reaction was found to be applicable to the nucleophilic trifluoromethylation of a broad spectrum of carbonyl compounds with satisfactory yields in general. DFT calculations have been performed to provide mechanistic insight into the present and related

  已开发出一种可行的亲核三氟甲基化方案，使用三氟乙醛水合物作为原子经济的三氟甲基源。发现该反应适用于广谱羰基化合物的亲核三氟甲基化反应，一般收率令人满意。已经进行了 DFT 计算，以提供对使用 2,2,2-三氟-1-甲氧基乙醇和六氟丙酮水合物的当前和相关反应的机理洞察。
• 4-PHENYL-6-(2,2,2-TRIFLUORO-1-PHENYLETHOXY)PYRIMIDINE-BASED COMPOUNDS AND METHODS OF THEIR USE
  申请人：Devasagayaraj Arokiasamy

  公开号：US20080153852A1

  公开（公告）日：2008-06-26

  Compounds of formula I are disclosed, as well as compositions comprising them and methods of their use to treat, prevent and/or manage diseases and disorders:

  公式I的化合物已被披露，以及包含它们的组合物和它们的使用方法，用于治疗、预防和/或管理疾病和障碍。