2-[hydroxy(4-trifluoromethylphenyl)methyl]cyclohexan-1-one | 1281971-27-4

• 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-[hydroxy(4-trifluoromethylphenyl)methyl]cyclohexan-1-one
• 英文别名: 2-(hydroxy(4-(trifluoromethyl)phenyl)methyl)cyclohexanone；2-[alpha-Hydroxy-4-(trifluoromethyl)benzyl]cyclohexanone；2-[hydroxy-[4-(trifluoromethyl)phenyl]methyl]cyclohexan-1-one
• CAS: 1281971-27-4
• 化学式: C₁₄H₁₅F₃O₂
• 分子量: 272.267
• InChiKey: AMAOWPFHJCGOMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对三氟甲基苯甲醛 、 环己酮 在 methyl 12-(D-prolinoylamino)cholate 作用下， 以 水 为溶剂， 反应 48.0h， 生成 2-[hydroxy(4-trifluoromethylphenyl)methyl]cyclohexan-1-one
  参考文献：
  名称：

  Methyl 12-[d-prolinoylamino]cholate as a versatile organocatalyst for the asymmetric aldol reaction of cyclic ketones

  摘要：

  The use of cholic acid derivative 1, bearing a D-prolinamide moiety linked at the 12-position of cholic acid methylester, as an organocatalyst in the asymmetric aldol reaction of cyclic ketones and aromatic aldehydes, gave the corresponding aldol products in good yield and ee up to 98%. This organocatalyst has proven to be efficient both in water and in organic solvent, where it has been used with a 1% loading. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.11.023

文献信息

• Reusable shuttles for exchangeable functional cargos: Reversibly assembled, magnetically powered organocatalysts for asymmetric aldol reactions
  作者：Carolina Mendoza、Augustin de la Croix、Paola Riente、Lluís Llorens、Javier de Mendoza、Miquel A. Pericàs

  DOI：10.1016/j.tet.2019.130592

  日期：2019.10

  supramolecular approach has been followed to support adamantyl substituted proline organocatalysts onto the surface of magnetite nanoparticles decorated with a β-cyclodextrin motif. The resulting magnetic nanoparticles (ca. ∼10 nm diameter) were used as modular, magnetically recyclable catalysts in the asymmetric aldol reaction of aromatic aldehydes with cyclic ketones in water. The catalytic assemblies

  已采用超分子方法将金刚烷基取代的脯氨酸有机催化剂负载到装饰有β-环糊精基序的磁铁矿纳米颗粒表面。所得的磁性纳米粒子（直径约10 nm）在水中芳香族醛与环酮的不对称羟醛反应中用作模块化的可磁循环催化剂。催化组件可以轻松地在有机介质中拆卸，回收的纳米颗粒（磁性化学梭）与另一种适当取代的催化单元（可替换的功能性货物）重新复合。
• L-proline derivatives based on a calix[4]arene scaffold as chiral organocatalysts for the direct asymmetric aldol reaction in water
  作者：Mehmet Aktas、Arzu Uyanik、Serkan Eymur、Mustafa Yilmaz

  DOI：10.1080/10610278.2015.1073288

  日期：2016.6.2

  water-compatible proline catalysts (4–6) derived from calixarene bearing a hydrophobic nature have been synthesised. It was found that the compound 4 was a highly efficient organocatalyst for aldol reactions occurred in the water. Under optimised reaction conditions, high yields (up to 82%), good enantioselectivities (ee up to 81%) and high diastereoselectivities (dr up to 91:9) were obtained.

  摘要 已经合成了一系列新的水相容脯氨酸催化剂 (4-6)，这些催化剂源自具有疏水性的杯芳烃。发现化合物4是在水中发生的羟醛反应的高效有机催化剂。在优化的反应条件下，获得了高产率（高达 82%）、良好的对映选择性（ee 高达 81%）和高非对映选择性（dr 高达 91:9）。
• Prolinamides of Aminouracils, Organocatalyst Modifiable by Complementary Modules
  作者：Karen M. Ruíz-Pérez、Beatriz Quiroz-García、Marcos Hernández-Rodríguez

  DOI：10.1002/ejoc.201800886

  日期：2018.11.8

  Prolinamide organocatalysts with aminouracils have the features of enhanced NH acidity, an additional hydrogen‐bond donor and the self‐assembly with complementary modules by Watson–Crick pairing. Each module affects the selectivity of the reaction and particularly 2,6‐diaminopyridine is beneficial to the selectivity in the reaction.

  带有氨基尿嘧啶的脯氨酰胺有机催化剂具有增强的NH酸度，额外的氢键供体以及通过沃森-克里克配对与互补模块自组装的特点。每个模块都会影响反应的选择性，特别是2,6-二氨基吡啶对反应的选择性有益。
• L-proline/cholesterol and diosgenin based thiourea cooperative system for the direct asymmetric aldol reaction in the presence of water
  作者：Serkan EYMUR、Enis TAŞCI、Arzu UYANIK、Mustafa YILMAZ

  DOI：10.3906/kim-2003-36

  日期：——

  successfully used as a cocatalyst for L-proline catalyzed aldol reactions in the presence of water. The anticonfigured products were obtained with good yields (up to 94%), high diastereoselectivities (up to 95:5), and high enantiomeric excesses (up to 93% ee ). The successful results for catalytic efficiency of L-proline in the presence of water reveal the importance of the hydrophobic nature of cholesterol

  合成了一系列胆固醇和基于疏水性的尿素和硫脲化合物，并成功地将其作为水存在下L-脯氨酸催化的羟醛反应的助催化剂。获得抗构型产物，具有良好的产率（高达94％），高的非对映选择性（高达95∶5）和高的对映体过量（高达93％ee）。L-脯氨酸在水存在下催化效率的成功结果表明，胆固醇和硫脲的薯os皂苷元部分的疏水性对在水存在下的反应性和选择性至关重要。
• Molecular-Sieves Controlled Diastereo- and Enantioselectivity: Unexpected Effect in the Organocatalyzed Direct Aldol Reaction
  作者：Jun-An Ma、Xiao-Juan Li、Guang-Wu Zhang、Lian Wang、Ming-Qing Hua

  DOI：10.1055/s-2008-1072586

  日期：2008.5

  An efficient asymmetric organocatalyst was developed for the direct aldol reaction between ketones and aldehydes to afford β-hydroxy ketones in high stereoselectivity (anti/syn up to 92:8, ee up to >99%). The key of the success was the use of activated molecular sieves (4 ŠMS), which acted as a water scavenger. The influence of additives such as water or different types of molecular sieves on the reactivity and stereoselectivity of the reaction was also studied.

  一种高效的非对称有机催化剂被开发出来，用于酮和醛之间的直接aldol反应，以高立体选择性（anti/syn高达92:8，ee高达>99%）制备β-羟基酮。成功的关键在于使用了活化的分子筛（4 Å MS），其作为水的清除剂。还研究了水分或不同类型分子筛等添加剂对反应活性和立体选择性的影响。