2-[hydroxyl(2,4-nitrophenyl)methyl]cyclohexanone | 1308852-53-0

• 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-[hydroxyl(2,4-nitrophenyl)methyl]cyclohexanone
• 英文别名: 2-[hydroxy-(2,4-dinitrophenyl)methyl]cyclohexanone；2-((2,4-dinitrophenyl)(hydroxy)methyl)cyclohexanone；2-[hydroxy(2,4-dinitrophenyl)methyl]cyclohexan-1-one；2-[(2,4-Dinitrophenyl)-hydroxymethyl]cyclohexan-1-one；2-[(2,4-dinitrophenyl)-hydroxymethyl]cyclohexan-1-one
• CAS: 1308852-53-0
• 化学式: C₁₃H₁₄N₂O₆
• 分子量: 294.264
• InChiKey: BMYVISFAXKXOLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  环己酮 、 2,4-二硝基苯甲醛 在 potassium hydroxide 作用下， 反应 24.0h， 以90%的产率得到2-[hydroxyl(2,4-nitrophenyl)methyl]cyclohexanone
  参考文献：
  名称：

  鸟苷硼酸盐水凝胶和能够在水中进行对映选择性羟醛反应的自组装纳米结构

  摘要：

  构建了鸟苷与4-(( l-脯氨酰胺)甲基)苯基硼酸自组装形成的鸟苷基水凝胶。G四重奏被K +离子选择性地稳定以形成自支撑透明水凝胶。这些鸟苷衍生的组装体用于催化水中的羟醛反应，无需任何添加剂，从而提供所需的产物转化率和对映选择性。小分子组分的受控测定表明，稳定的组装体是实现高对映选择性催化的确定物种。目前的催化体系可以通过简单的提取很容易地回收，并且经过四次循环后仍能获得良好的反应性能。

  DOI：

  10.1021/acs.joc.1c02573

文献信息

• SULFONAMIDE-BASED ORGANOCATALYSTS AND METHOD FOR THEIR USE
  申请人：Carter Rich Garrett

  公开号：US20100184986A1

  公开（公告）日：2010-07-22

  Organocatalysts, particularly proline sulfonamide organocatalysts, having a first general formula as follows are disclosed. Embodiments of a method for using these organocatalysts also are disclosed. The method comprises providing a disclosed organocatalyst, and performing a reaction, often an enantioselective or diastereoselective reaction, using the organocatalyst. Solely by way of example, disclosed catalysts can be used to perform aldol reactions, conjugate additions, Michael additions, Robinson annulations, Mannich reactions, α-aminooxylations, α-hydroxyaminations, α-aminations and alkylation reactions. Certain of such reactions are intramolecular cyclizations used to form cyclic compounds, such as 5- or 6-membered rings, having one or more chiral centers. Disclosed organocatalysts generally are much more soluble in typical solvents used for organic synthesis than are known compounds. Moreover, the reaction yield is generally quite good with disclosed compounds, as is their enantioselective and diastereoselective effectiveness.

  披露了具有如下一般公式之一的有机催化剂，尤其是脯氨酸磺酰胺有机催化剂。还披露了使用这些有机催化剂的方法的实施例。该方法包括提供一种披露的有机催化剂，并使用该有机催化剂进行反应，通常是立体选择性的反应或对映选择性反应。仅作为示例，披露的催化剂可用于进行aldol反应、共轭加成、Michael加成、Robinson环化反应、Mannich反应、α-氨基氧化、α-羟基胺化、α-胺化和烷基化反应。其中一些反应是分子内环化反应，用于形成具有一个或多个手性中心的环状化合物，例如5或6元环。披露的有机催化剂通常比已知的化合物更容易溶于用于有机合成的典型溶剂中。此外，使用披露化合物的反应收率通常相当好，它们的对映选择性和非对映选择性效果也很好。
• Preparation of Immobilized L-Prolinamide Via Enzymatic Polymerization of Phenolic L-Prolinamide and Evaluation of Its Catalytic Performance for Direct Asymmetric Aldol Reaction
  作者：Chengke Qu、Wenshan Zhao、Lei Zhang、Yuanchen Cui

  DOI：10.1002/chir.22302

  日期：2014.4

  L‐prolinamide. The catalytic performance of the resultant polymer‐supported L‐prolinamide for direct asymmetric aldol reaction between aromatic aldehyde and cyclohexanone was studied. The results show that as prepared L‐prolinamide can catalyze the aldol reaction at room temperature in the presence of H2O. Relevant aldol addition products are obtained with good yields (up to 91%), high diastereoselectivities

  允许以辣根过氧化物酶为催化剂参与酚L-脯氨酰胺的酶促聚合反应，生成固定化的L-脯氨酰胺。研究了所得聚合物负载的L-脯氨酰胺对芳族醛与环己酮之间直接不对称羟醛反应的催化性能。结果表明，制得的L-脯氨酰胺可在H 2 O存在下在室温下催化羟醛反应。获得了相关的羟醛加成产物，收率高（高达91％），高非对映选择性（高达6:94 dr ）和中等对映选择性（最高87％ee）。此外，标题聚合物负载的催化剂可以回收并重复使用至少五个循环，而活性几乎保持不变。手性26：209–213，2014年。©2014 Wiley Periodicals，Inc.
• Chitosan-supported cinchonine as an efficient organocatalyst for direct asymmetric aldol reaction in water
  作者：Wenshan Zhao、Chengke Qu、Lili Yang、Yuanchen Cui

  DOI：10.1016/s1872-2067(14)60248-5

  日期：2015.3

  Abstract Chitosan-supported succinic anhydride-cinchonine (CTS-SA-CN) was synthesized via a two-step route with succinic anhydride as the linker. The catalyst was used to promote the direct asymmetric aldol reaction between cyclohexanone and a variety of aromatic aldehydes in aqueous medium. Aldol adducts were obtained in excellent yields (up to 99%) and good enantioselectivities (up to 96% ee). The

  摘要 以琥珀酸酐为连接体，通过两步法合成了壳聚糖负载的琥珀酸酐-辛可宁（CTS-SA-CN）。该催化剂用于促进环己酮与多种芳香醛在水性介质中的直接不对称醛醇反应。以优异的产率（高达 99%）和良好的对映选择性（高达 96% ee）获得了羟醛加合物。CTS-SA-CN催化剂使用后只需过滤即可成功回收，重复使用5次，活性无明显损失。
• Rationally designed organocatalyst for direct asymmetric aldol reaction in the presence of water
  作者：Chao Wang、Yi Jiang、Xiao-xia Zhang、Yi Huang、Bo-gang Li、Guo-lin Zhang

  DOI：10.1016/j.tetlet.2007.04.037

  日期：2007.6

  A rationally designed organocatalyst for direct asymmetric aldol reaction in the presence of water has been developed. High yield (up to 99%), diastereoselectivity (up to 99:1) and enantioselectivity (up to 97%) were obtained under optimal conditions.

  已经开发出合理设计的用于在水存在下直接不对称醛醇缩合反应的有机催化剂。在最佳条件下，可获得高收率（最高99％），非对映选择性（最高99：1）和对映选择性（最高97％）。
• Efficient asymmetric aldol reaction catalyzed by polyvinylidene chloride-supported ionic liquid/l-proline catalyst system
  作者：Xuan Zhang、Wenshan Zhao、Chengke Qu、Lili Yang、Yuanchen Cui

  DOI：10.1016/j.tetasy.2012.03.023

  日期：2012.4

  chloride (PVDC)-supported ionic liquids were derived from 4-dimethylaminopyridine and used together with l-proline in water as efficient asymmetric organocatalysts for direct asymmetric aldol reactions between cyclohexanone and a variety of aromatic aldehydes at room temperature. These PVDC-supported ionic liquids/l-proline catalyst systems have been used as asymmetric organocatalysts to afford the corresponding

  从4-二甲基氨基吡啶衍生了一系列聚偏二氯乙烯（PVDC）负载的离子液体，并与l-脯氨酸一起在水中用作有效的不对称有机催化剂，用于室温下环己酮与各种芳香醛之间的直接不对称羟醛反应。这些PVDC负载的离子液体/ l-脯氨酸催化剂体系已用作不对称有机催化剂，以中等至高的分离产率（高达99％），非对映选择性高达6:94和出色的对映选择性提供相应的羟醛产物。高达98％。此外，它们可以容易地回收，并且在七次回收后仅显示出选择性的轻微降低。