1,1,1-trifluoro-2-phenylbutan-2-ol | 2248-23-9

• 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: 1,1,1-trifluoro-2-phenylbutan-2-ol
• 英文别名: α-Ethyl-α-trifluormethyl-benzylalkohol；1,1,1-Trifluoro-2-phenyl-2-butanol
• CAS: 2248-23-9
• 化学式: C₁₀H₁₁F₃O
• 分子量: 204.192
• InChiKey: DQMMTAXIJXTESZ-UHFFFAOYSA-N

物化性质

• 沸点：
  242.2±40.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  三氟甲烷 、 苯丙酮 在 三(三甲基硅)胺 、 四甲基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以28%的产率得到1,1,1-trifluoro-2-phenylbutan-2-ol
  参考文献：
  名称：

  Nucleophilic Trifluoromethylation of Carbonyl Compounds and Disulfides with Trifluoromethane and Silicon-Containing Bases

  摘要：

  Provided that DMF (or another N,N-dialkylformamide) is present in the reaction medium, at least in a catalytic amount, fluoroform trifluoromethylates efficiently carbonyl compounds, even enolizable ones, when opposed to (TMS)(2)N- M+, generated in situ from N(TMS)(3) and M+ F- or RO- Na+ When F- is used ina catalytic amount, silylated alpha-(trifluoromethyl)carbinols are-obtained: in this case, the four-component system HCF3/N(TMS)(3)/catalytic F-/catalytic DMF behaves like the Ruppert's reagent, especially as far as nonenolizable carbonyl compounds are concerned (CF3SiMe3 remains more efficient for enolizable carbonyl compounds). This process involves an adduct between DMF and -CF3 which is the true trifluoromethylating agent. In the same way, fluoroform efficiently trifluoromethylates disulfides and diselenides when deprotonated with a strong base selected from t-BuOK or N(SiMe3)(3)/Me4NF (or TBAT). t-BuOK is more adapted to the trifluoromethylation of aryl disulfides whereas N(SiMe3)(3)/F- is well suited to that of aliphatic disulfides.

  DOI：

  10.1021/jo000150s

文献信息

• [EN] EXPANDED THERAPEUTIC POTENTIAL IN NITROHETEROARYL ANTIMICROBIALS<br/>[FR] POTENTIEL THÉRAPEUTIQUE ÉTENDU DANS DES ANTIMICROBIENS À NITROHÉTÉROARYLE
  申请人：UNIV CALIFORNIA

  公开号：WO2014205414A1

  公开（公告）日：2014-12-24

  Disclosed herein are antimicrobial compounds compositions, pharmaceutical compositions, the use and preparation thereof. Some embodiments relate to imidazole, thiazole, and furan derivatives and their use as therapeutic agents.

  本文披露了抗微生物化合物组合物、药物组合物及其使用和制备。一些实施例涉及咪唑、噻唑和呋喃衍生物及其作为治疗剂的用途。
• Catalytic asymmetric β-hydrogen transfer reduction of α-trifluoromethyl aromatic ketones with diethylzinc
  作者：Huayin Huang、Hua Zong、Guangling Bian、Ling Song

  DOI：10.1016/j.tetasy.2015.06.017

  日期：2015.8

  The catalytic asymmetric β-hydrogen transfer reduction of α-trifluoromethyl ketones using diethylzinc as the β-hydrogen donor was developed with the use of phosphinamide chiral ligand. The corresponding alcohol products were afforded in good yields with up to 73% ee. This method was successfully applied to the chemo- and enantioselective reduction of α-methyl/trifluoromethyl diketone, affording 88%

  利用次膦酰胺手性配体，开发了以二乙基锌为β-氢供体的α-三氟甲基酮的催化不对称β-氢转移还原反应。以高达73％ee的高收率提供相应的醇产物。该方法成功应用于α-甲基/三氟甲基二酮的化学和对映选择性还原，提供了88％的收率和70％ee的氟化羟基酮产物。
• Expanding Mg-Zn Hybrid Chemistry: Inorganic Salt Effects in Addition Reactions of Organozinc Reagents to Trifluoroacetophenone and the Implications for a Synergistic Lithium-Magnesium-Zinc Activation
  作者：David R. Armstrong、William Clegg、Pablo García-Álvarez、Alan R. Kennedy、Matthew D. McCall、Luca Russo、Eva Hevia

  DOI：10.1002/chem.201100866

  日期：2011.7.18

  study sheds new light on the constitution of the organometallic species involved in this important synthetic tool. Investigations into the metathesis reactions of equimolar amounts of Grignard reagents (RMgX) and ZnCl2 in THF led to the isolation of novel magnesium–zinc hybrids, [(thf)2Mg(μ‐Cl)3ZnR}2] (R=Et, tBu, nBu or o‐OMe‐C6H4), which exhibit an unprecedented structural motif in mixed magnesium–zinc

  许多有机转化都依赖于有机锌化合物，这些化合物是通过有机锂或格氏试剂与合适的锌前体通过盐复分解（交换）反应制得的。通过结合X射线晶体学，NMR光谱学和DFT计算，这项研究为这一重要的合成工具所涉及的有机金属物种的构成提供了新的思路。对等摩尔量的格氏试剂（RMgX）和ZnCl 2在THF中的复分解反应的研究导致了新型镁-锌杂化物的分离，[（thf）2 Mg（μ‐Cl）3 ZnR} 2 ]（R = Et，t Bu，n Bu或o -OMe-C 6 H 4），在混合的镁锌化学中展现出前所未有的结构基序。此外，EtMgCl与ZnCl 2反应的理论模型表明，在热力学上，混合金属化合物的形成要比预期的同金属产物RZnCl和MgCl 2更好。这项研究还评估了杂化3对敏感的酮三氟苯乙酮的烷基化能力，揭示了当引入LiCl作为添加剂时反应的化学选择性显着提高。该观察结果与最近在合成中的相关突破相结合，指出存在三边的Li
• Catalytic Enantioselective Addition of Diethylzinc to Trifluoromethyl Ketones
  作者：Kimberly Yearick、Christian Wolf

  DOI：10.1021/ol8015012

  日期：2008.9.1

  A procedure for nucleophilic addition of diethylzinc to trifluoromethyl ketones was developed. The TMEDA-catalyzed method converts aromatic substrates to the corresponding 2-aryl-1,1,1-trifluorobutan-2-ols in up to 99% yield, and it is also applicable to less reactive aliphatic ketones if stoichiometric ligand amounts are employed. The first asymmetric variant producing tertiary alcohols with up to 61% ee when TBOX is used as catalyst is described.