(2R)-2-[(S)-hydroxy(4-nitrophenyl)methyl]cyclohexanone

• 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: (2R)-2-[(S)-hydroxy(4-nitrophenyl)methyl]cyclohexanone
• 英文别名: 2-(hydroxy(4-nitrophenyl)methyl)cyclohexanone；(R)-2-((S)-hydroxy(4-nitrophenyl)methyl)cyclohexanone；2-(hydroxy(4-nitrophenyl)methyl)cyclohexan-1-one；(R)-2-((S)-hydroxy(4-nitrophenyl)methyl)cyclohexan-1-one；(2R,1'S)-2-[hydroxy-(4-nitrophenyl)methyl]cyclohexan-1-one；(2R,1'S)-2-(hydroxy(p-nitrophenyl)methyl)cyclohexan-1-one；(2R)-2-[(1S)-hydroxy(4-nitrophenyl)methyl]cyclohexanone；(2R,1'S)-2-[hydroxy(4-nitrophenyl)methyl]-cyclohexanone；2-(hydroxyl-(p-nitrophenyl)methyl)cyclohexan-1-one；2-(hydroxy(p-nitrophenyl)methyl)cyclohexan-1-one；(2R)-2-[(S)-hydroxy-(4-nitrophenyl)methyl]cyclohexan-1-one
• 化学式: C₁₃H₁₅NO₄
• 分子量: 249.266
• InChiKey: LWDGESCTOIIBJJ-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对硝基苯甲醇 在 manganese(IV) oxide 、 三氟甲磺酸 、 9-deoxy-9-epi-cinchonidineamine 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 13.0h， 生成 (2R)-2-[(S)-hydroxy(4-nitrophenyl)methyl]cyclohexanone
  参考文献：
  名称：

  从苄醇开始的有机催化对映选择性羟醛和亨利反应

  摘要：

  描述了从苄基型醇开始的开创性醛醇和亨利反应。遵循醇一锅策略成功完成了醇醛反应，而亨利反应则首次按照顺序操作进行了。在两种方法中，均以良好的产率和高的对映选择性获得了对映体富集的产物。我们还证明，在对少量酸敏感的反应中，使用醇代替醛可能是改善这些反应结果的良好解决方案。

  DOI：

  10.1002/adsc.201701351

文献信息

• L-proline derivatives based on a calix[4]arene scaffold as chiral organocatalysts for the direct asymmetric aldol reaction in water
  作者：Mehmet Aktas、Arzu Uyanik、Serkan Eymur、Mustafa Yilmaz

  DOI：10.1080/10610278.2015.1073288

  日期：2016.6.2

  water-compatible proline catalysts (4–6) derived from calixarene bearing a hydrophobic nature have been synthesised. It was found that the compound 4 was a highly efficient organocatalyst for aldol reactions occurred in the water. Under optimised reaction conditions, high yields (up to 82%), good enantioselectivities (ee up to 81%) and high diastereoselectivities (dr up to 91:9) were obtained.

  摘要 已经合成了一系列新的水相容脯氨酸催化剂 (4-6)，这些催化剂源自具有疏水性的杯芳烃。发现化合物4是在水中发生的羟醛反应的高效有机催化剂。在优化的反应条件下，获得了高产率（高达 82%）、良好的对映选择性（ee 高达 81%）和高非对映选择性（dr 高达 91:9）。
• Prolinamides of Aminouracils, Organocatalyst Modifiable by Complementary Modules
  作者：Karen M. Ruíz-Pérez、Beatriz Quiroz-García、Marcos Hernández-Rodríguez

  DOI：10.1002/ejoc.201800886

  日期：2018.11.8

  Prolinamide organocatalysts with aminouracils have the features of enhanced NH acidity, an additional hydrogen‐bond donor and the self‐assembly with complementary modules by Watson–Crick pairing. Each module affects the selectivity of the reaction and particularly 2,6‐diaminopyridine is beneficial to the selectivity in the reaction.

  带有氨基尿嘧啶的脯氨酰胺有机催化剂具有增强的NH酸度，额外的氢键供体以及通过沃森-克里克配对与互补模块自组装的特点。每个模块都会影响反应的选择性，特别是2,6-二氨基吡啶对反应的选择性有益。
• Diastereoselective Synthesis of 4,5‘-Bis-proline Compounds via Reductive Dimerization of <i>N</i>-Acyloxyiminium Ions
  作者：Franca Zanardi、Andrea Sartori、Claudio Curti、Lucia Battistini、Gloria Rassu、Giuseppe Nicastro、Giovanni Casiraghi

  DOI：10.1021/jo062406l

  日期：2007.3.1

  A short, practical synthesis of novel, unsymmetrical 4,5‘-bis-proline compounds has been achieved, highlighted by the application of an unprecedented samarium diiodide-driven regio- and diastereocontrolled reductive dimerization of N-acyloxyiminium ions generated from readily available 2-methoxy-5-silyloxymethyl-N-Boc pyrrolidines. The title proline dimers proved to be pertinent metal-free catalysts

  已实现了新颖，不对称的4,5'-双脯氨酸化合物的简短，实用合成，这一点的突出之处在于应用了前所未有的sa二碘化物驱动的由N-酰氧基亚胺离子生成的N-酰氧基亚胺离子的区域和非对映体控制的还原二聚化反应。甲氧基-5-甲硅烷氧基甲基-N - Boc吡咯烷。标题脯氨酸二聚体被证明是在醇醛和曼尼希反应中相关的无金属催化剂。
• Readily Tunable and Bifunctional <scp>l</scp>-Prolinamide Derivatives:  Design and Application in the Direct Enantioselective Aldol Reactions
  作者：Jia-Rong Chen、Hai-Hua Lu、Xin-Yong Li、Lin Cheng、Jian Wan、Wen-Jing Xiao

  DOI：10.1021/ol0520323

  日期：2005.9.1

  [reaction: see text] Readily tunable and bifunctional L-prolinamides as novel organocatalysts have been developed, and their catalytic activities were evaluated in the direct asymmetric Aldol reactions of various aromatic aldehydes and cyclohexanone. High isolated yields (up to 94%), enantioselectivities (up to 99% ee), and anti-diastereoselectivities (up to 99:1) were obtained under the optimal conditions

  [反应：见正文]已开发出易于调节的双功能L-脯氨酰胺作为新型有机催化剂，并在各种芳族醛和环己酮的直接不对称Aldol反应中评估了它们的催化活性。在最佳条件下，获得了高分离产率（高达94％），对映选择性（高达99％ee）和抗非对映选择性（高达99：1）。
• Oxazoline-Substituted Prolinamide-Based Organocatalysts for the Direct Intermolecular Aldol Reaction between Cyclohexanone and Aromatic Aldehydes
  作者：Simon Doherty、Julian G. Knight、Amy McRae、Ross W. Harrington、William Clegg

  DOI：10.1002/ejoc.200700922

  日期：2008.4

  Oxazoline-substituted prolinamides catalyse the direct asymmetric aldol reaction between cyclohexanone and a range of aldehydes to give excellent conversions and enantioselectivities up to 84 % under optimum conditions. Reactions were highly substrate-specific with electron-deficient aldehydes giving the highest yields and ee values. The absolute configuration of the 4-chlorobenzaldehyde-derived product

  恶唑啉取代的脯氨酰胺催化环己酮和一系列醛之间的直接不对称醛醇反应，在最佳条件下提供出色的转化率和高达 84% 的对映选择性。反应具有高度的底物特异性，缺电子醛的产率和 ee 值最高。4-氯苯甲醛衍生产物的绝对构型通过单晶X射线分析明确确定为（2S，1'R），产物的立体化学显示主要由脯氨酸片段的立体化学决定.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)