(2S)-2-[(R)-hydroxy-(p-cyanophenyl)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)-2-[(R)-hydroxy-(p-cyanophenyl)methyl]cyclohexan-1-one
• 英文别名: 4-((R)-hydroxy((S)-2-oxocyclohexyl)methyl)benzonitrile；4-(hydroxy(2-oxocyclohexyl)methyl)benzonitrile；2-[hydroxy-(4-cyanophenyl)methyl]cyclohexanone；(S)-2-[(R)-hydroxy(4-cyanophenyl)methyl]cyclohexanone；(S)-2-((R)-hydroxy(4-cyanophenyl)methyl)cyclohexan-1-one；(2S,1'R)-2-(hydroxy-(4-cyanophenyl)methyl)cyclohexan-1-one；(2S,1'R)-2-(hydroxy(p-cyanophenyl)methyl)cyclohexan-1-one；4-{(1R)-hydroxy[(1S)-2-oxocyclohexyl]methyl}benzonitrile；(2S)-2-[(1R)-(4-cyanophenyl)hydroxymethyl]cyclohexanone；2-(hydroxy(4-cyanophenyl)methyl)cyclohexan-1-one；2alpha-[(R)-4-Cyano-alpha-hydroxybenzyl]cyclohexanone；4-[(R)-hydroxy-[(1S)-2-oxocyclohexyl]methyl]benzonitrile
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: XIGKYYNFQYOADS-OCCSQVGLSA-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：

  环己酮 、 4-氰基苯甲醛 在 (N'-benzyl-N'-D-prolyl)-trans-4-hydroxy-L-proline hydrazide 、 三氟乙酸 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以95%的产率得到(2S)-2-[(R)-hydroxy-(p-cyanophenyl)methyl]cyclohexan-1-one
  参考文献：
  名称：

  （N'-苄基-N'-D-脯氨酰基）-反式-4-羟基-L-脯氨酸酰肼催化环己酮的不对称直接羟醛反应

  摘要：

  一个新的脯氨酸催化剂，即（N' -苄基- N' - d脯氨酰） -反式-4-羟基-大号脯氨酸酰肼，已经制备并证明是环己酮和芳族的不对称醛醇缩合反应优异的催化剂醛，可提供高达98：2的dr和98％的ee。

  DOI：

  10.1002/cjoc.201190051

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）。
• 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）。
• Highly efficient organocatalysts for the asymmetric aldol reaction
  作者：C. G. Jacoby、P. H. V. Vontobel、M. F. Bach、P. H. Schneider

  DOI：10.1039/c7nj04424k

  日期：——

  synthetic route. The highly efficient five step methodology did not require intermediary purification and provided the compounds in high yields. The catalysts were successfully applied in the asymmetric direct aldol reaction between aromatic aldehydes and cyclic ketones in aqueous media. Aldol adducts were obtained in high yields with perfect stereoselectivities (up to >99% e.e. and >19 : 1 d.r.).

  通过容易获得的合成途径制备了同时包含噻唑烷/吡咯烷和咪唑循环的新型双功能有机催化剂。高效的五步法无需中间纯化，即可提供高收率的化合物。该催化剂已成功地用于水性介质中芳族醛与环酮之间的不对称直接羟醛反应中。高产率地获得了醛醇加合物，具有完美的立体选择性（高达> 99％ee和> 19：1 dr）。
• Enamine-Metal Lewis Acid Bifunctional Catalysis: Application to Direct Asymmetric Aldol Reaction of Ketones
  作者：Zhenghu Xu、Philias Daka、Ilya Budik、Hong Wang、Fu-Quan Bai、Hong-Xing Zhang

  DOI：10.1002/ejoc.200900678

  日期：2009.9

  Unprecedented bifunctional enamine–metal Lewis acid catalysts have been developed. In this bifunctional catalytic system, a tridentate ligand tethered with a chiral secondary amine was designed to solve the acid–base self-quenching problem leading to catalyst inactivation. This new bifunctional enamine–metal Lewis acid catalyst was found to catalyze aldol reactions of ketones efficiently in high yields

  已经开发出前所未有的双功能烯胺-金属路易斯酸催化剂。在这种双功能催化系统中，设计了一种与手性仲胺相连的三齿配体，以解决导致催化剂失活的酸碱自淬灭问题。发现这种新型双功能烯胺-金属路易斯酸催化剂能够以高产率有效催化酮的羟醛反应，并具有良好到优异的非对映选择性和对映选择性。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009）
• L-proline/cholesterol and diosgenin based thiourea cooperative system for the direct asymmetric aldol reaction in the presence of water
  作者：Serkan EYMUR、Enis TAŞCI、Arzu UYANIK、Mustafa YILMAZ

  DOI：10.3906/kim-2003-36

  日期：——

  successfully used as a cocatalyst for L-proline catalyzed aldol reactions in the presence of water. The anticonfigured products were obtained with good yields (up to 94%), high diastereoselectivities (up to 95:5), and high enantiomeric excesses (up to 93% ee ). The successful results for catalytic efficiency of L-proline in the presence of water reveal the importance of the hydrophobic nature of cholesterol

  合成了一系列胆固醇和基于疏水性的尿素和硫脲化合物，并成功地将其作为水存在下L-脯氨酸催化的羟醛反应的助催化剂。获得抗构型产物，具有良好的产率（高达94％），高的非对映选择性（高达95∶5）和高的对映体过量（高达93％ee）。L-脯氨酸在水存在下催化效率的成功结果表明，胆固醇和硫脲的薯os皂苷元部分的疏水性对在水存在下的反应性和选择性至关重要。