4-hydroxy-4-(2-trifluoromethylphenyl)-butan-2-one

• 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-hydroxy-4-(2-trifluoromethylphenyl)-butan-2-one
• 英文别名: 4-hydroxy-4-(2-trifluoromethylphenyl)butane-2-one；4-Hydroxy-4-[2-(trifluoromethyl)phenyl]butan-2-one；4-hydroxy-4-[2-(trifluoromethyl)phenyl]butan-2-one
• 化学式: C₁₁H₁₁F₃O₂
• 分子量: 232.202
• InChiKey: WOVWDWQBPKJEGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-hydroxy-4-(2-trifluoromethylphenyl)-butan-2-one 在 NH₂-Val-(D-Pro)-Gly-Leu-OH 、 苯甲酸 作用下， 以 乙醇 为溶剂， 反应 160.0h， 以37%的产率得到(R)-4-hydroxy-4-(2'-(trifluoromethyl)phenyl)butan-2-one
  参考文献：
  名称：

  Highly enantioselective biomimetic intramolecular dehydration: kinetic resolution of β-hydroxy ketones catalyzed by β-turn tetrapeptides

  摘要：

  Racemic beta-hydroxy ketones were kinetically resoluted into the enantiopure isomers and (E)-alpha,beta-unsaturated ketones using catalytic asymmetric intramolecular dehydration for the first time. Synthetic tetrapeptides were used to imitate fatty acid dehydratases to efficiently discriminate racemic beta-hydroxy ketones, enantioselectively catalyze the intramolecular dehydration, and result in highly enantioenriched beta-hydroxy and (E)-alpha,beta-unsaturated ketones in the environmentally benign process. Mechanistically, the high discrimination of the racemic substrates and successive enantioselective dehydration are highly dependent on the cooperative catalysis of the NH2 and COOH groups of the peptide. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.087
• 作为产物：
  描述：

  邻三氟甲基苯甲醛 、 丙酮 在 enzyme from root of Daucus carota 作用下， 以 aq. phosphate buffer 为溶剂， 反应 10.0h， 以84%的产率得到4-hydroxy-4-(2-trifluoromethylphenyl)-butan-2-one
  参考文献：
  名称：

  从酶胡萝卜根催化的不对称交叉醛醇缩合反应

  摘要：

  从特定的金黄色葡萄球菌根催化的芳族醛与丙酮的不对称交叉羟醛交联反应中分离出一种新型酶，以优异的收率（高达95％）和对映选择性（高达99％）提供了交叉羟醛交联产物。还提出了合理的反应机理。

  DOI：

  10.1016/j.tetlet.2016.08.056

文献信息

• The effect of acid–base pairing on catalysis: An efficient acid–base functionalized catalyst for aldol condensation
  作者：R ZEIDAN、M DAVIS

  DOI：10.1016/j.jcat.2007.02.005

  日期：2007.4.25

  Acid-base bifunctionalized heterogeneous catalysts may be capable of exhibiting reactivity not achievable with homogeneous catalysts. We investigated the effect of pK(a) of the acid component of mesoporous solids containing acid-bast, bifunctionality on their catalytic ability toward aldol condensation between 4-nitrobenzaldehyde and acetone. We found that higher levels of aldol product conversion were obtained when weaker acid components (phosphoric, carboxylic vs sulfonic) were used, an indication of the importance of the equilibrium between free acid and free base and the resulting neutralized ion pair in the catalytic capability of acid-base functionalized materials. A catalyst containing primary amine groups in combination with carboxylic acid groups (with similar chemical functionalities to proline) was found to be a superior catalyst in this aldol reaction with a number of different electrophilic components. (C) 2007 Elsevier Inc. All rights reserved.
• Enzyme from Daucus carota root catalyzed asymmetric cross aldol reaction
  作者：Chiranjit Acharya、Madhumita Mandal、Trina Dutta、Anil Kumar Ghosh、Parasuraman Jaisankar

  DOI：10.1016/j.tetlet.2016.08.056

  日期：2016.9

  A novel enzyme was isolated from specific variety of Daucus carota root catalyzed asymmetric cross aldol reaction of aromatic aldehydes with acetone to afford cross aldol products with excellent yield (up to 95%) and enantioselectivity (up to 99%). A plausible mechanism of the reaction has also been proposed.

  从特定的金黄色葡萄球菌根催化的芳族醛与丙酮的不对称交叉羟醛交联反应中分离出一种新型酶，以优异的收率（高达95％）和对映选择性（高达99％）提供了交叉羟醛交联产物。还提出了合理的反应机理。
• Highly enantioselective biomimetic intramolecular dehydration: kinetic resolution of β-hydroxy ketones catalyzed by β-turn tetrapeptides
  作者：Zhi-Xue Du、Li-Yuan Zhang、Xin-Yuan Fan、Feng-Chun Wu、Chao-Shan Da

  DOI：10.1016/j.tetlet.2013.03.087

  日期：2013.5

  Racemic beta-hydroxy ketones were kinetically resoluted into the enantiopure isomers and (E)-alpha,beta-unsaturated ketones using catalytic asymmetric intramolecular dehydration for the first time. Synthetic tetrapeptides were used to imitate fatty acid dehydratases to efficiently discriminate racemic beta-hydroxy ketones, enantioselectively catalyze the intramolecular dehydration, and result in highly enantioenriched beta-hydroxy and (E)-alpha,beta-unsaturated ketones in the environmentally benign process. Mechanistically, the high discrimination of the racemic substrates and successive enantioselective dehydration are highly dependent on the cooperative catalysis of the NH2 and COOH groups of the peptide. (C) 2013 Elsevier Ltd. All rights reserved.