3-((S)-hydroxy((R)-2-oxocyclohexyl)methyl)benzonitrile | 1332625-58-7

• 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-((S)-hydroxy((R)-2-oxocyclohexyl)methyl)benzonitrile
• 英文别名: 2-[hydroxy(3-cyanophenyl)methyl]cyclohexanone；3-[(S)-hydroxy[(1R)-2-oxocyclohexyl]methyl]benzonitrile；3-[hydroxy-(2-oxo-cyclohexyl)-methyl]-benzonitrile；2-(hydroxy-(m-cyanophenyl)methyl)cyclohexan-1-one；3-[(S)-hydroxy-[(1R)-2-oxocyclohexyl]methyl]benzonitrile
• CAS: 1332625-58-7
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: PRQCLMXSOJHZEP-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氰基苯甲醛 、 环己酮 在 2,4-二硝基酚 、 (S)-N-((S)-1-oxo-1-((4-(piperidin-1-yl)pyridin-2-yl)amino)-propan-2-yl)pyrrolidine-2-carboxamide 、 sodium chloride 作用下， 以 水 为溶剂， 反应 6.0h， 以96%的产率得到3-((S)-hydroxy((R)-2-oxocyclohexyl)methyl)benzonitrile
  参考文献：
  名称：

  Proline-based dipeptides as efficient organocatalysts for asymmetric aldol reactions in brine

  摘要：

  Simple N-proline-based dipeptides with two N-H groups in combination with 2,4-dinitrophenol (DNP) catalyze the direct asymmetric aldol reactions of aldehydes with a broad range of ketones to furnish the corresponding aldol products in high yields (up to 99%) and with high enantioselectivities (up to 97%) and diastereoselectivities (up to > 99:1, anti/syn) at room temperature and in brine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.017

文献信息

• 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。
• 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。
• Facile one-pot fabrication of magnetic nanoparticles (MNPs)-supported organocatalysts using phosphonate as an anchor point through direct co-precipitation method
  作者：Jingwei Wan、Lu ding、Tao Wu、Xuebing Ma、Qian Tang

  DOI：10.1039/c4ra04720f

  日期：——

  Novel MNP-supported organocatalysts were prepared by one-pot co-precipitation and surface modification using phosphonate as an anchor point, and exhibited excellent performance in aqueous asymmetric aldol reactions.

  通过一锅共沉淀和表面修饰使用磷酸酯作为锚点制备了新型MNP支持的有机催化剂，并在水相不对称Aldol反应中表现出优异性能。
• Combining prolinamides with 2-pyrrolidinone: Novel organocatalysts for the asymmetric aldol reaction
  作者：Ismini Vlasserou、Maria Sfetsa、Dimitrios-Triantafyllos Gerokonstantis、Christoforos G. Kokotos、Panagiota Moutevelis-Minakakis

  DOI：10.1016/j.tet.2018.03.054

  日期：2018.5

  identified as excellent organocatalysts for the aldol reaction. The combination of prolinamides with derivatives bearing the 2-pyrrolidinone scaffold, deriving from pyroglutamic acid, led to the identification of novel organocatalysts for the intermolecular asymmetric aldol reaction. The new hybrids were tested both in organic and aqueous media. Among the compounds tested, 22 afforded the best results in petroleum

  肽，特别是脯氨酰胺已被确认为醛醇缩合反应的优良有机催化剂。脯氨酰胺与衍生自焦谷氨酸的带有2-吡咯烷酮骨架的衍生物的组合导致鉴定用于分子间不对称醛醇缩合反应的新型有机催化剂。新型杂交种在有机和水性介质中均经过测试。在测试的化合物中，有22种化合物在石油醚中的效果最好，而25种化合物在盐水中的产率和选择性高。然后，利用各种酮和醛，高收率（高达100％），优异的非对映异构体（高达97：3 dr）和对映选择性（高达99％）获得醛醇缩合反应的产物。ee）。
• Organic functionalization of ultradispersed nanodiamond: synthesis and applications
  作者：Wen-Wei Zheng、Yi-Han Hsieh、Yu-Chung Chiu、Sian-Jhu Cai、Chia-Liang Cheng、Chinpiao Chen

  DOI：10.1039/b904302k

  日期：——

  This work describes the chemical modification of ultradispersed nanodiamond results in the enrichment of the surface hydroxyl groups as by FT-IR, TGA, RGA-MS and XRD measurements. These hydroxyl groups can be conveniently functionalized with long chain alcohols (oxyhexanol) for easy manipulation of different functional groups. The surface loading of the oxyhexanol groups were found to be 0.13 mmol/g of nanodiamond. The functionalities on the surface of the modified nanodiamond afford a new solid phase for the synthesis of peptides to facilitate the covalent attachment of drug molecules. The conjugation of chiral ligands with a nanodiamond yields a new enantioselective heterogeneous catalyst that exhibits moderate to good enantioselectivity in the asymmetric aldol reaction.

  这项工作描述了超分散纳米金刚石的化学修饰，结果表明表面羟基的富集，通过傅里叶变换红外光谱（FT-IR）、热重分析（TGA）、气体放大质谱（RGA-MS）和X射线衍射（XRD）测量。这些羟基可以便利地与长链醇（氧己醇）功能化，以便于不同功能团的操作。氧己醇在纳米金刚石表面的负载量为0.13 mmol/g。改性纳米金刚石表面的功能团为合成肽提供了一种新的固相，以促进药物分子的共价结合。手性配体与纳米金刚石的结合产生了一种新的不对称选择性杂化催化剂，在不对称醛醇反应中表现出中等至良好的不对称选择性。