(S)-2-((R)-hydroxy(3-trifluoromethylphenyl)methyl)cyclohexan-1-one | 1224881-43-9

• 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: (S)-2-((R)-hydroxy(3-trifluoromethylphenyl)methyl)cyclohexan-1-one
• 英文别名: (S)-2-((R)-hydroxy(3-trifluoromethylphenyl)methyl)cyclohexanone；2-(hydroxy-(m-(trifluoromethyl)phenyl)methyl)cyclohexan-1-one；(2S)-2-[(R)-hydroxy-[3-(trifluoromethyl)phenyl]methyl]cyclohexan-1-one
• CAS: 1224881-43-9
• 化学式: C₁₄H₁₅F₃O₂
• 分子量: 272.267
• InChiKey: MWNOOOOYMCXCGM-YPMHNXCESA-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：

  3-三氟甲基苯甲醛 、 环己酮 在 1-[3,5-Bis(trifluoromethyl)phenyl]-3-[3-[[27-[3-[[3,5-bis(trifluoromethyl)phenyl]carbamothioylamino]propoxy]-5,11,17,23-tetratert-butyl-26,28-dihydroxy-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]oxy]propyl]thiourea 、 L-脯氨酸 作用下， 以 正己烷 为溶剂， 反应 24.0h， 以99%的产率得到
  参考文献：
  名称：

  Proline–calixarene thiourea host–guest complex catalyzed enantioselective aldol reactions: from nonpolar solvents to the presence of water

  摘要：

  A proline-calix[4]arene thiourea host-guest complex catalyzed intermolecular aldol reaction of aromatic aldehydes with cyclohexanone has been developed. The anti-configured products were obtained in good yields and with high enantioselectivities. The reaction is proposed to work via a modified Houk-List model, where the carboxylate part of the praline constitutes as a supramolecular system with the thiourea. The outcome of the study indicates the influence of the calix[4]arene thiourea on both the reactivity and selectivity in a non-polar reaction medium, even in the presence of water at moderate temperatures. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.01.015

文献信息

• Organocatalytic asymmetric aldol reaction using protonated chiral 1,2-diamines
  作者：Jae Ho Shim、Min-Joon Kim、Ji Yeon Lee、Kyoung Hoon Kim、Deok-Chan Ha

  DOI：10.1016/j.tetlet.2020.152295

  日期：2020.9

  Organic-catalyzed stereoselective reactions have gained attention because they avoid the problems associated with metal catalysts, but existing catalysts based on proline have limitations. Therefore, (R,R)-(+)-1,2-diphenylethylenediamine (DPEN) was selectively mono-N-alkylated through reductive alkylation and used as an organic catalyst for the aldol reaction. Using a variety of aldehydes in the catalytic

  由于有机催化的立体选择反应避免了与金属催化剂有关的问题，因此引起了人们的关注，但是现有的基于脯氨酸的催化剂存在局限性。因此，（R，R）-（+）-1,2-二苯基乙二胺（DPEN）通过还原烷基化被选择性地单-N-烷基化，并用作醛醇缩合反应的有机催化剂。在催化的醛醇缩合反应中使用多种醛，N-烷基化的DPEN催化剂从伯胺发展为烯胺和亚胺中间体，并获得了高收率（80％）和对映选择性（90％）。发现氮的位阻手性二胺的-烷基取代基和铵部分与芳族醛的氧之间的氢键决定了对映选择性。测试了各种芳族​​醛，并且吸电子取代基导致了良好的产率，而供电子取代基通过使醛的羰基失活而导致了较差的产率。此外，邻位取代基比对位取代基具有更高的立体选择性，因为立体效果得到增强。
• Direct asymmetric aldol reactions between aldehydes and ketones catalyzed by l-tryptophan in the presence of water
  作者：Zhaoqin Jiang、Hui Yang、Xiao Han、Jie Luo、Ming Wah Wong、Yixin Lu

  DOI：10.1039/b921460g

  日期：——

  Primary amino acids and their derivatives were investigated as catalysts for the direct asymmetric aldol reactions between ketones and aldehydes in the presence of water, and L-tryptophan was shown to be the best catalyst. Solvent effects, substrate scope and the influence of water on the reactions were investigated. Quantum chemical calculations were performed to understand the origin of the observed

  研究了伯氨基酸及其衍生物作为在水存在下酮与醛之间直接不对称醛醇缩合反应的催化剂，L-色氨酸是最好的催化剂。研究了溶剂效应，底物范围和水对反应的影响。进行量子化学计算以了解观察到的立体选择性的起源。
• Glucosamine-Based Primary Amines as Organocatalysts for the Asymmetric Aldol Reaction
  作者：Jyoti Agarwal、Rama Krishna Peddinti

  DOI：10.1021/jo1023156

  日期：2011.5.6

  Glucosamine derivatives have been synthesized starting from commercially available N-acetyl-D-glucosamine/glucosamine hydrochloride and have been employed successfully as efficient organocatalysts for the direct asymmetric aldol reaction between cyclohexanone and aryl aldehydes having diversified substituents. Furthermore, the anomeric effect of various groups present at the anomeric position on the catalytic activity of these organocatalysts was also studied.
• Proline–calixarene thiourea host–guest complex catalyzed enantioselective aldol reactions: from nonpolar solvents to the presence of water
  作者：Ezgi Demircan、Serkan Eymur、Ayhan Sıtkı Demir

  DOI：10.1016/j.tetasy.2014.01.015

  日期：2014.3

  A proline-calix[4]arene thiourea host-guest complex catalyzed intermolecular aldol reaction of aromatic aldehydes with cyclohexanone has been developed. The anti-configured products were obtained in good yields and with high enantioselectivities. The reaction is proposed to work via a modified Houk-List model, where the carboxylate part of the praline constitutes as a supramolecular system with the thiourea. The outcome of the study indicates the influence of the calix[4]arene thiourea on both the reactivity and selectivity in a non-polar reaction medium, even in the presence of water at moderate temperatures. (C) 2014 Elsevier Ltd. All rights reserved.