3-[hydroxy(4-nitrophenyl)methyl]tetrahydro-4H-pyran-4-one | 1092371-49-7

• 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: 3-[hydroxy(4-nitrophenyl)methyl]tetrahydro-4H-pyran-4-one
• 英文别名: 3-[Hydroxy-(4-nitrophenyl)methyl]oxan-4-one
• CAS: 1092371-49-7
• 化学式: C₁₂H₁₃NO₅
• 分子量: 251.239
• InChiKey: ISLLWPBIQZQNMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  四氢吡喃酮 、 对硝基苯甲醛 在 DL-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 生成 3-[hydroxy(4-nitrophenyl)methyl]tetrahydro-4H-pyran-4-one
  参考文献：
  名称：

  新型磺酰基聚苯乙烯负载的脯氨酰胺在水中对映选择性羟醛反应的催化剂

  摘要：

  已经合成了五种衍生自负载在市售磺酰基聚苯乙烯上的1，正二胺的五种新型脯氨酰胺，并将其成功地用于水中或在纯净条件下的非对映体和对映体选择性羟醛反应中。在催化剂和以AcOH为助催化剂的情况下，通过不同环己酮衍生物与芳族和杂芳族醛的反应获得了优异的dr和er。负载的有机催化剂在低负荷（5摩尔％）下工作，表现出与均相脯氨酰胺相似的性能，并且在活化后可以重复使用，而不会损失活性。

  DOI：

  10.1016/j.tet.2013.10.093

文献信息

• Molecular-Sieves Controlled Diastereo- and Enantioselectivity: Unexpected Effect in the Organocatalyzed Direct Aldol Reaction
  作者：Jun-An Ma、Xiao-Juan Li、Guang-Wu Zhang、Lian Wang、Ming-Qing Hua

  DOI：10.1055/s-2008-1072586

  日期：2008.5

  An efficient asymmetric organocatalyst was developed for the direct aldol reaction between ketones and aldehydes to afford β-hydroxy ketones in high stereoselectivity (anti/syn up to 92:8, ee up to >99%). The key of the success was the use of activated molecular sieves (4 ŠMS), which acted as a water scavenger. The influence of additives such as water or different types of molecular sieves on the reactivity and stereoselectivity of the reaction was also studied.

  一种高效的非对称有机催化剂被开发出来，用于酮和醛之间的直接aldol反应，以高立体选择性（anti/syn高达92:8，ee高达>99%）制备β-羟基酮。成功的关键在于使用了活化的分子筛（4 Å MS），其作为水的清除剂。还研究了水分或不同类型分子筛等添加剂对反应活性和立体选择性的影响。
• Proline dipeptides containing fluorine moieties as oganocatalysts for the asymmetric aldol reaction
  作者：Ardiol Ahmetlli、Nikoleta Spiliopoulou、Angeliki Magi-Oikonomopoulou、Dimitrios-Triantaffylos Gerokonstantis、Panagiota Moutevelis-Minakakis、Christoforos G. Kokotos

  DOI：10.1016/j.tet.2018.08.038

  日期：2018.10

  demonstrated, where aromatic aldehydes afforded products in high yields (up to 100%) with excellent diastereo- (up to 95:5) and enantioselectivities (up to 97%), whereas the aliphatic aldehydes afforded also excellent selectivities, but relatively low yield. A simple addition of fluorine to a dipeptide analogue affords organocatalysts with new interesting properties that can catalyze the aldol reaction

  合成了由脯氨酸，苯丙氨酸和苯胺-或苯酚-氟衍生物组成的一系列二肽类似物。在分子间不对称醛醇缩合反应中，在有机介质和水性介质中均评估了它们的催化能力。当2-CF 3时，苯胺-氟衍生物被证明是优越的，并获得了最佳结果。使用了苯胺。证明了由芳香族和脂肪族醛以及不同的酮组成的多种底物范围，其中芳香族醛提供高收率（高达100％）的产品，具有出色的非对映异构性（高达95：5）和对映选择性（高达90％）。 97％），而脂族醛也提供了优异的选择性，但是产率相对较低。将氟简单地添加到二肽类似物中可以提供具有新的有趣特性的有机催化剂，该特性可以更有效地催化羟醛反应。
• Electrostatic Repulsion and Hydrogen-Bonding Interactions in a Simple<i>N</i>-Aryl-<scp>L</scp>-valinamide Organocatalyst Control the Stereoselectivity in Asymmetric Aldol Reactions
  作者：Yuya Tanimura、Kenji Yasunaga、Kaori Ishimaru

  DOI：10.1002/ejoc.201301138

  日期：2013.10

  A novel stereocontrol method for asymmetric aldol reactions of aldehydes with ketones is described. The stereoselectivity of the products is controlled by the electrostatic repulsion and hydrogen-bonding interactions of an N-aryl-L-valinamide catalyst. The use of this catalyst in a cross-aldol reaction allows easy access to bioactive 3-cyclohexanone-3-hydroxy-2-oxindole with excellent diastereo- (syn/anti

  描述了一种用于醛与酮的不对称羟醛反应的新型立体控制方法。产物的立体选择性受 N-芳基-L-缬氨酰胺催化剂的静电排斥和氢键相互作用控制。在交叉羟醛反应中使用该催化剂可以轻松获得具有优异非对映-（syn/anti = >99:1）和对映选择性（>99%ee）的生物活性 3-cyclohexone-3-hydroxy-2-oxindole。
• 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。
• Primary amine-metal Lewis acid bifunctional catalysts: the application to asymmetric direct aldol reactions
  作者：Zhenghu Xu、Philias Daka、Hong Wang

  DOI：10.1039/b912728c

  日期：——

  The first example of metal Lewis acid-primary amine bifunctional cooperative catalyst derived from primary amino acids was developed, and it was found to catalyze aldol reactions of cyclic ketones highly efficiently with very good to excellent stereoselectivities.

  开发了衍生自伯氨基酸的金属路易斯酸-伯胺双官能协同催化剂的第一个实例，发现它可以非常有效地催化环状酮的醛醇缩合反应，具有非常好的至优异的立体选择性。