(S)-α,3-bis(trifluoromethyl)-benzenemethanol | 80446-62-4

• 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: (S)-α,3-bis(trifluoromethyl)-benzenemethanol
• 英文别名: (S)-2,2,2-Trifluoro-1-(3-(trifluoromethyl)phenyl)ethan-1-ol；(1S)-2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethanol
• CAS: 80446-62-4
• 化学式: C₉H₆F₆O
• 分子量: 244.136
• InChiKey: BSMNENKVFMPEGA-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-三氟甲基-A,A,A-三氟苯乙酮 在 N-<α-methylbenzyl>-1-propyl-2,4-dimethyl-1,4-dihydronicotinamide 作用下， 以 丙酮 为溶剂， 生成 (S)-α,3-bis(trifluoromethyl)-benzenemethanol 、 (R)-α,3-bis(trifluoromethyl)-benzenemethanol
  参考文献：
  名称：

  通过 NAD(P)H 模型减少。34. 取代基对三氟苯乙酮不对称还原的影响

  摘要：

  取代和未取代的 α,α,α-三氟苯乙酮被手性 NAD(P)H 模型 (RR-Me2PNPH) 还原。释放电子和吸电子取代基都比未取代的化合物具有更好的光学产率。结果已被解释为涉及初始电子转移过程的三步机制。

  DOI：

  10.1246/bcsj.54.3486

文献信息

• Reduction by a Model of NAD(P)H. 34. Substituent Effect on Asymmetric Reduction of Trifluoroacetophenones
  作者：Atsuyoshi Ohno、Jun-ichi Nakai、Kaoru Nakamura、Takehiko Goto、Shinzaburo Oka

  DOI：10.1246/bcsj.54.3486

  日期：1981.11

  Substituted and unsubstituted α,α,α-trifluoroacetophenones were reduced by a chiral NAD(P)H-model (RR-Me2PNPH). Both electron-releasing and -withdrawing substituents give better optical yields than unsubstitued compound. The result has been interpreted in terms of three-step mechanism which involves initial electron-transfer process.

  取代和未取代的 α,α,α-三氟苯乙酮被手性 NAD(P)H 模型 (RR-Me2PNPH) 还原。释放电子和吸电子取代基都比未取代的化合物具有更好的光学产率。结果已被解释为涉及初始电子转移过程的三步机制。
• Platinum-catalyzed enantioselective hydrogenation of aryl-substituted trifluoroacetophenones
  作者：Matthias von Arx、Tamas Mallat、Alfons Baiker

  DOI：10.1016/s0957-4166(01)00524-9

  日期：2001.12

  The hydrogenation of 2,2,2-trifluoroacetophenones with different aryl-substituents (CF(3), N(Me)(2) and Me) has been studied over Pt/Al(2)O(3) modified by cinchonidine, its hydrochloride or O-methyl cinchonidine. Electron-withdrawing groups increased and electron-releasing groups decreased the rate and enantioselectivity of these reactions, although steric effects (with m- or p-substituents) were also critical. The 92% e.e. achieved in the hydrogenation of 2,2,2-trifluoroacetophenone is the highest value obtained so far in this reaction using any heterogeneous catalyst system. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Rational electronic tuning of CBS catalyst for highly enantioselective borane reduction of trifluoroacetophenone
  作者：Toshinobu Korenaga、Kenji Nomura、Kazutaka Onoue、Takashi Sakai

  DOI：10.1039/c0cc03706k

  日期：——

  α,α,α-Trifluoroacetophenone (2), which is susceptible to noncatalytic reduction by BH3, could be reduced to chiral alcohol up to 90% ee by using electronically tuned-CBS catalyst (1) with BH3. The enantioselectivities highly correlated with the differential orbital energies between 1–BH3 adduct and 2, which were calculated by DFT method.

  α,α,α-三氟乙酰苯（2），该物质易受BH3非催化还原，可通过使用电子调谐CBS催化剂（1）与BH3反应，将其还原为手性醇，最高可达90%的ee值。通过DFT方法计算，其对映选择性与1–BH3加合物和2之间的轨道能量差异高度相关。