(2S,1'R)-2-(hydroxy(2,4-dinitrophenyl)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: (2S,1'R)-2-(hydroxy(2,4-dinitrophenyl)methyl)cyclohexan-1-one
• 英文别名: (2S,10R)-2-(hydroxy(2,4-dinitrophenyl)methyl)cyclohexan-1-one；(R)-2-[(S)-hydroxyl(2,4-nitrophenyl)methyl]cyclohexanone；(R)-2-[(S)-hydroxy-(2,4-dinitrophenyl)methyl]cyclohexanone；2-((2,4-dinitrophenyl)(hydroxy)methyl)cyclohexanone；(2R)-2-[(S)-(2,4-dinitrophenyl)-hydroxymethyl]cyclohexan-1-one
• 化学式: C₁₃H₁₄N₂O₆
• 分子量: 294.264
• InChiKey: BMYVISFAXKXOLL-GXFFZTMASA-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：

  2,4-二硝基苯甲醛 、 环己酮 在 三氟甲磺酸 、 (1R,2R)-N,N-dibenzyl-1,2-diaminocyclohexane 作用下， 以 neat (no solvent) 为溶剂， 反应 15.0h， 以98%的产率得到(2S,1'R)-2-(hydroxy(2,4-dinitrophenyl)methyl)cyclohexan-1-one
  参考文献：
  名称：

  新型手性伯-叔二胺-布朗斯台德酸盐有机催化剂，用于高度对映选择性的直接抗羟醛和顺曼尼希反应

  摘要：

  只需花费几步即可轻松地从廉价的市售对映纯材料制备新型伯叔叔二胺催化剂。这种有机催化剂可以有效地催化直接的不对称羟醛和曼尼希反应。可以以高达99：1的反/合成比和> 98％ee获得抗醛醇缩合产物，而可以以高达99：1的合成/反比和> 99％ee合成辛-曼尼希产物。 。催化剂 1c 可以有效地大规模使用，同时将抗羟醛和对曼尼希反应的对映选择性保持在同一水平，这为工业应用提供了很大的可能性。

  DOI：

  10.1007/s11164-012-0667-x

文献信息

• 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％）。
• Guanosine Borate Hydrogel and Self-Assembled Nanostructures Capable of Enantioselective Aldol Reaction in Water
  作者：Zhaohang Chen、Pengcheng Zhou、Yuanxia Guo、Anna、Jiakun Bai、Renzhong Qiao、Chao Li

  DOI：10.1021/acs.joc.1c02573

  日期：2022.3.4

  hydrogel. These guanosine-derived assemblies were used to catalyze the aldol reaction in water without any additives, affording desirable conversion and enantioselectivity of the product. The controlled assays of small-molecule components indicated that the stable assemblies were the definite species that achieved high enantioselective catalysis. The current catalytic system can be readily recovered by

  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。
• Polymerization of l-proline functionalized styrene and its catalytic performance as a supported organocatalyst for direct enantioselective aldol reaction
  作者：Guozhang Guo、Yufeng Wu、Xiaowei Zhao、Jing Wang、Lei Zhang、Yuanchen Cui

  DOI：10.1016/j.tetasy.2016.06.014

  日期：2016.9

  As an alternative approach to the graft modification of polymers to fabricate polymer-supported chiral organocatalysts in a bottom-up fashion, L-prolinamide functionalized polymers were prepared by general solution homopolymerization or copolymerization of L-proline functionalized styrene monomer in the presence of 1,4-divinylbenzene as the crosslinking agent. The catalytic performance of the as-prepared heterogeneous catalysts towards the direct enantioselective aldol reaction of ketones with a series of aromatic aldehydes was explored. Our findings indicate that the as-prepared heterogeneous catalysts can afford relevant aldol addition products with good yields (up to 96%), high diastereoselectivities (up to 8:92 dr) and excellent enantiomeric excess (up to 96%); they also exhibit good recyclability, retaining high yield and rate as well as good selectivity after several cycles. (C) 2016 Elsevier Ltd. All rights reserved.