4-(2,4-dinitrophenyl)-4-hydroxybutan-2-one | 1193067-50-3

• 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: 4-(2,4-dinitrophenyl)-4-hydroxybutan-2-one
• 英文别名: (R)-4-hydroxy-4-(2,4-dinitrophenyl)butan-2-one；(4R)-4-(2,4-dinitrophenyl)-4-hydroxybutan-2-one
• CAS: 1193067-50-3
• 化学式: C₁₀H₁₀N₂O₆
• 分子量: 254.199
• InChiKey: DZXSFEDFDGEUPD-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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 、 丙酮 在 C₂₉H₃₂N₄O₂ 、 zinc trifluoromethanesulfonate 作用下， 以 水 为溶剂， 反应 0.25h， 以67%的产率得到4-(2,4-dinitrophenyl)-4-hydroxybutan-2-one
  参考文献：
  名称：

  氮丙啶氨基脲锌（II）配合物催化的直接不对称羟醛缩合反应

  摘要：

  在锌（II）催化的非对映和对映选择性直接醛醇缩合反应中，探索了从N-三苯基甲基-氮丙啶-2-碳酰肼衍生的先前获得的氨基脲作为配体。氮丙啶-氨基脲与Zn（II）的配合物是丙酮和羟基丙酮与NO 2取代的芳香醛在水存在下反应的有效催化剂。

  DOI：

  10.1016/j.tetlet.2014.02.131

文献信息

• Bioinspired Catalysis: Self-Assembly of a Protein and DNA as a Catalyst for the Aldol Reaction in Aqueous Media
  作者：Guangxun Li、Zhuo Tang、Hongxin Liu、Ying-wei Wang、Shiqi Zhang

  DOI：10.1055/s-0036-1591854

  日期：2018.3

  electrostatic interaction in situ proved to be efficient in catalyzing aldol reactions under mild conditions in water. By using a self-assembling catalytic system formed from protamine and DNA, aldol adducts were obtained with high yields and moderate enantioselectivities. Preliminary experiments demonstrated that the chirality of the DNA could be effectively transferred to the reaction product through

  一种有趣的仿生催化剂由容易获得的 DNA 和蛋白质通过原位静电相互作用形成，被证明在水中温和条件下可有效催化羟醛反应。通过使用由鱼精蛋白和 DNA 形成的自组装催化系统，以高产率和中等对映选择性获得了羟醛加合物。初步实验表明，DNA 的手性可以通过结合的分子或蛋白质有效地转移到反应产物上。
• 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。
• <i>N</i>-Prolinylanthranilamide Pseudopeptides as Bifunctional Organocatalysts for Asymmetric Aldol Reactions
  作者：Anthony J. Pearson、Santanu Panda

  DOI：10.1021/ol202284n

  日期：2011.10.21

  Proline anthranilamide-based pseudopeptides were shown to be effective organocatalysts for enantioselective direct aldol reactions of a selection of aldehydes with various ketones with excellent yield, enantioselectivity up to 99% and anti to syn diastereoselectivity up to 25:1.
• Zinc(II) mediated asymmetric aldol condensation catalyzed by chiral aziridine ligands
  作者：Adam M. Pieczonka、Szymon Jarzyński、Zuzanna Wujkowska、Stanisław Leśniak、Michał Rachwalski

  DOI：10.1016/j.tetlet.2015.10.027

  日期：2015.11

  Exploration of chiral aziridine ethers and aziridine alcohols as ligands for the Zn(II) catalyzed enantio-selective direct aldol condensations reaction is described. The reaction of acetone with NO2-substituted aromatic aldehydes in the presence of water gave the desired adducts in moderate chemical yields (40-70%) and good to excellent enantiomeric excesses (80-98% ee). (C) 2015 Elsevier Ltd. All rights reserved.
• A novel trifunctional organocatalyst for the asymmetric aldol reaction: a facile enantioselective synthesis of β-hydroxyketones
  作者：B.V. Subba Reddy、K. Bhavani、A. Raju、J.S. Yadav

  DOI：10.1016/j.tetasy.2011.05.001

  日期：2011.4

  A new L-prolinamide trifunctional catalyst has been developed for the enantioselective aldol reaction of various aromatic and aliphatic aldehydes with acetone. This method provides high yields of beta-hydroxyketones (up to 90%) with good enantioselectivity (up to 92%) at a low catalyst loading (10 mol %). (C) 2011 Elsevier Ltd. All rights reserved.