2-(hydroxy(2-cyanophenyl)methyl)cyclohexanone | 1332625-59-8

• 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: 2-(hydroxy(2-cyanophenyl)methyl)cyclohexanone
• 英文别名: 2-[(S)-hydroxy-[(1R)-2-oxocyclohexyl]methyl]benzonitrile
• CAS: 1332625-59-8
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: SGMFFANMODFVJC-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：

  2-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 2.0h， 以97%的产率得到2-(hydroxy(2-cyanophenyl)methyl)cyclohexanone
  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

• l-Valine Dipeptide Organocatalysts with Two Amide Units for the Direct Asymmetric Aldol Reaction in Brine
  作者：Wenbo Huang、Hua Tian、Hao Xu、Liangyu Zheng、Qingwen Liu、Suoqin Zhang

  DOI：10.1007/s10562-011-0589-z

  日期：2011.6

  a primary amine group and two amide units have been developed and evaluated in the direct asymmetric intermolecular aldol reaction of 4-nitrobenzaldehyde and cyclohexanone. When 2,4-dinitrophenol (DNP) was used as an acidic additive, the catalyzed reactions of various aldehydes and ketones gave the corresponding aldol products with moderate to high enantioselectivities (up to 95%) and diastereoselectivities

  一系列含有伯胺基团和两个酰胺单元的缬氨酸二肽有机催化剂已被开发并在 4-硝基苯甲醛和环己酮的直接不对称分子间醛醇反应中进行评估。当使用 2,4-二硝基苯酚 (DNP) 作为酸性添加剂时，各种醛和酮的催化反应得到相应的醛醇产物，具有中到高的对映选择性（高达 95%）和非对映选择性（高达 >99/1， anti/syn) 在 3c 存在于盐水中。图形摘要。
• Novel Primary Amine Organocatalysts Derived from Cinchona Alkaloids for Asymmetric Direct Aldol Reactions in Brine
  作者：Wen-Bo Huang、Qing-Wen Liu、Liang-Yu Zheng、Suo-Qin Zhang

  DOI：10.1007/s10562-010-0478-x

  日期：2011.1

  A series of Cinchona alkaloids derived organocatalysts have been developed and evaluated in the direct asymmetric intermolecular aldol reaction of 4-nitrobenzaldehyde and cyclohexanone. The catalyzed reactions of various aldehydes and ketones gave the corresponding aldol products with moderate to high enantioselectivities (up to 92%) and diastereoselectivities (up to >99/1, anti/syn) in the presence

  在 4-硝基苯甲醛和环己酮的直接不对称分子间羟醛反应中开发并评估了一系列金鸡纳生物碱衍生的有机催化剂。在盐水中存在 3e 的情况下，各种醛和酮的催化反应得到了相应的醛醇产物，具有中到高的对映选择性（高达 92%）和非对映选择性（高达 >99/1，anti/syn）。图形摘要
• Sulfonation of pyrene-based metal–organic framework for the encapsulation of chiral organocatalyst and application in asymmetric aldol addition
  作者：Congwei Gao、Xingtao Deng、Jianing Zhang、Xuebing Ma

  DOI：10.1016/j.apcata.2022.119003

  日期：2023.1

  Encapsulation of bulky chiral chiral organocatalysts into metal-organic frameworks (MOFs) is a challenge because of difficult control on the crystallinity of MOFs. Herein, Zr6(μ3-OH)8(OH)8TBAPy)2 (NU-1000) with is sulfonated at − 30 °C by ClSO3H at low concentration, and then bulky cinchona alkaloid-derived chiral primary amines, 9-amino (9-deoxy)epi-quinine (QNNH2) and 9-amino(9-deoxy) epi-cinchonidine

  将大体积手性手性有机催化剂封装到金属有机骨架 (MOF) 中是一项挑战，因为很难控制 MOF 的结晶度。在此，Zr 6 ( μ 3 -OH) 8 (OH) 8 TBAPy) 2 (NU-1000) with 在− 30 °C 下被低浓度的 ClSO 3 H 磺化，然后生成庞大的金鸡纳生物碱衍生的手性伯胺， 9-氨基（9-脱氧）表-奎宁 (QNNH 2 ) 和 9-氨基(9-脱氧)表-辛可尼定(CDNH 2 ) 通过酸碱反应固定在 NU-1000 上。摩尔比为 QNNH 2 /-SO 3H = 0.96，NU-1000 支持的 QNNH 2具有高表面积 (677 m 2 g −1 )、大孔体积 (0.48 cc g −1 ) 和最可能的 3.0 nm 孔径显示高产率 (86–95 %)在环己酮与带有吸电子基团的苯甲醛（-NO 2和 -CN ）的不对称羟醛反应中具有良好至优异的非对映选择性（反/顺=
• Aqueous asymmetric aldol reaction catalyzed by nanomagnetic solid acid SO42−/Zr(OH)4–Fe3O4
  作者：Tao Wu、Jingwei Wan、Xuebing Ma

  DOI：10.1016/s1872-2067(14)60222-9

  日期：2015.3

  Magnetic solid acid catalysts SO42-/Zr(OH)(4)-Fe3O4 were prepared using magnetic Fe3O4 nanoparticles, ZrOCl2 center dot 8H(2)O, and sulfuric acid as starting materials in the calcination temperature range 110-650 degrees C. The properties of the magnetic solid acid, such as loaded SO42- content, acid distribution, surface morphology, and porous structure, were characterized. In the aqueous asymmetric aldol reaction of various benzaldehydes with strong electron-withdrawing groups (R = NO2 and CN), good to excellent catalytic performance (83%-100% yield, 86.0%-95.6% ee anti, and anti/syn = 88-96/12-4) was achieved. These nanomagnetic solid acids can be quantitatively recycled from the reaction mixture using an external magnet and reused five times without significant loss of catalytic activity. (C) 2015, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.