2-(hydroxy-(3,5-bis(trifluoromethyl)phenyl)methyl)cyclohexan-1-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: 2-(hydroxy-(3,5-bis(trifluoromethyl)phenyl)methyl)cyclohexan-1-one
• 英文别名: (2S)-2-[(alphaR)-alpha-Hydroxy-3,5-bis(trifluoromethyl)benzyl]cyclohexanone；(2S)-2-[(R)-[3,5-bis(trifluoromethyl)phenyl]-hydroxymethyl]cyclohexan-1-one
• 化学式: C₁₅H₁₄F₆O₂
• 分子量: 340.265
• InChiKey: RSTSVKQFKJDAQY-YPMHNXCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3,5-双三氟甲基苯甲醛 、 环己酮 在 L-叔亮氨酸 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 168.0h， 生成 2-(hydroxy-(3,5-bis(trifluoromethyl)phenyl)methyl)cyclohexan-1-one 、 2-(hydroxy-(3,5-bis(trifluoromethyl)phenyl)methyl)cyclohexan-1-one
  参考文献：
  名称：

  Lt-亮氨酸催化的环酮的直接不对称醛醇反应

  摘要：

  描述了 Lt-亮氨酸催化的直接不对称醛醇反应。在室温下对硝基苯甲醛与环酮的羟醛反应中，Lt-亮氨酸表现出催化活性，导致中等到高的非对映选择性和对映选择性。使用环庚酮或环辛酮作为底物导致产生顺式选择性产物。

  DOI：

  10.1002/ejoc.201001413

文献信息

• 3,3′-Bithiophene-Based Chiral Bisphosphine Oxides as Organocatalysts in Silicon-Derived Lewis Acid Mediated Reactions
  作者：Sergio Rossi、Tiziana Benincori、Laura Maria Raimondi、Maurizio Benaglia

  DOI：10.1055/s-0039-1690777

  日期：2020.4

  This account summarizes the development of new biheteroaromatic chiral bisphosphine oxides. 3,3′-Bithiophene-based phosphine oxides (BITIOPOs) have been successfully used as organocatalysts to promote Lewis base catalyzed, Lewis acid mediated stereoselective transformations. These highly electron-rich compounds, in combination with trichorosilyl derivatives (allyltrichlorosilane and silicon tetrachloride)

  该帐户总结了新的双杂芳族手性双膦氧化物的开发。3,3'-联噻吩基氧化膦 (BITIOPO) 已成功用作有机催化剂，以促进路易斯碱催化、路易斯酸介导的立体选择性转化。这些高度富电子的化合物与三氯甲硅烷基衍生物（烯丙基三氯硅烷和四氯化硅）结合，生成高价硅物质，在高度非对映选择性和对映选择性有机反应中充当手性路易斯酸。详细讨论了与这些应用程序相关的几个相关示例。
• 一种手性磺酰胺脯氨酸类双官能催化剂及其制备方法和应用
  申请人：广东工业大学

  公开号：CN111499660A

  公开（公告）日：2020-08-07

  本发明公开了一种新型手性磺酰胺类双官能催化剂及其制备方法和应用。所述催化剂包括化合物A或化合物B，所述化合物A的分子结构如式(Ⅰ)所示，所述化合物B的分子结构如式(Ⅱ)所示：其中，R1取代基为羟基或硅烷基；R2取代基为氢或烷基；Tf表示三氟甲基磺酰基。本发明的磺酰胺类双官能团催化剂具有高光学纯度，该催化剂属于双官能催化剂，能够有效催化不对称羟醛反应，该类催化剂介导的不对称催化方法，反应条件温和，产率高，操作步骤简单，安全可靠，绿色环保，产率高达99％，非对映异构体和对映异构体的选择性高达99％。
• Catalytically Active Multicompartment Micelles
  作者：Eman Ahmed、Jinwon Cho、Lulu Friedmann、Seung Soon Jang、Marcus Weck

  DOI：10.1021/jacsau.2c00367

  日期：2022.10.24

  segregated domains and their use as supports for aqueous catalysis. A library of poly(norbornene)-based amphiphilic bottlebrush copolymers containing covalently attached l-proline in the hydrophobic, styrene, and pentafluorostyrene domains and a poly(ethylene glycol)-containing repeat unit as the hydrophilic block have been synthesized using ring-opening metathesis polymerization. Interaction parameter (χ)

  This article presents the self-assembly behavior of multicompartment micelles (MCMs) in water into morphologies with multiple segregated domains and their use as supports for aqueous catalysis. A library of poly(norbornene)-based amphiphilic bottlebrush copolymers containing covalently attached l-proline in the hydrophobic, styrene, and pentafluorostyrene domains and a poly(ethylene glycol)-containing
• Biheteroaromatic diphosphine oxides-catalyzed stereoselective direct aldol reactions
  作者：Sergio Rossi、Maurizio Benaglia、Andrea Genoni、Tiziana Benincori、Giuseppe Celentano

  DOI：10.1016/j.tet.2010.11.009

  日期：2011.1

  A highly stereoselective direct aldol condensation of ketones to aromatic aldehydes was realized; the trichlorosilyl enolether generated in situ in the presence of tetrachlorosilane is activated by catalytic amounts of an enantiomerically pure biheteroaromatic phosphine oxide to react with aldehydes, coordinated as well as activated by the chiral cationic hypervalent silicon species. This Lewis acid-mediated Lewis base-catalyzed transformation allowed, starting from two carbonyl compounds, to directly synthesize beta-hydroxy ketones generally with high anti stereoselectivity and up to 93% ee for the anti isomer. (C) 2010 Elsevier Ltd. All rights reserved.
• L-t-Leucine-Catalyzed Direct Asymmetric Aldol Reaction of Cyclic Ketones
  作者：Takuya Kanemitsu、Atsushi Umehara、Michiko Miyazaki、Kazuhiro Nagata、Takashi Itoh

  DOI：10.1002/ejoc.201001413

  日期：2011.2

  L-t-Leucine-catalyzed direct asymmetric aldol reactions are described. In the aldol reaction of p-nitrobenzaldehyde with a cyclic ketone at room temperature, L-t-leucine exhibits catalytic activity resulting in moderate to high diastereo- and enantioselectivity. Use of cycloheptanone or cyclooctanone as a substrate resulted in production of the syn selective product.

  描述了 Lt-亮氨酸催化的直接不对称醛醇反应。在室温下对硝基苯甲醛与环酮的羟醛反应中，Lt-亮氨酸表现出催化活性，导致中等到高的非对映选择性和对映选择性。使用环庚酮或环辛酮作为底物导致产生顺式选择性产物。