(S)-1-(pyridin-4-yl)-2-nitroethanol | 1200403-99-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (S)-1-(pyridin-4-yl)-2-nitroethanol
• 英文别名: (1S)-2-nitro-1-pyridin-4-ylethanol
• CAS: 1200403-99-1
• 化学式: C₇H₈N₂O₃
• 分子量: 168.152
• InChiKey: SGMASOGGNOSBGC-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  78.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-吡啶甲醛 、 硝基甲烷 在 2-(1,1-dimethylethyl)-6-[[[(1R,2R)-2-[(4-pyridinylmethyl)amino]cyclohexyl]amino]methyl]phenol 、 copper diacetate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以96%的产率得到(S)-1-(pyridin-4-yl)-2-nitroethanol
  参考文献：
  名称：

  Enantioselective Nitroaldol (Henry) Reaction of p-Nitrobenzaldehyde and Nitromethane Using a Copper (II) Complex Derived from (R,R)-1,2-Diaminocyclohexane: (1S)-1-(4-Nitrophenyl)-2-nitroethane-1-ol

  摘要：

  DOI：

  10.15227/orgsyn.090.0052

文献信息

• Catalytic effect and recyclability of imidazolium-tagged bis(oxazoline) based catalysts in asymmetric Henry reactions
  作者：Zhi-Ming Zhou、Zhi-Huai Li、Xiao-Yan Hao、Jun Zhang、Xiao Dong、Ying-Qiang Liu、Wen-Wen Sun、Dan Cao、Jin-Liang Wang

  DOI：10.1039/c2ob06434k

  日期：——

  imidazolium ionic liquids have been developed as a new class of versatile catalysts. C(2)-symmetric imidazolium-tagged bis(oxazoline) ligands were prepared, and the anions of the ligands were altered. The catalysts based on the new ligands and Cu(OAc)(2).H(2)O were applied in asymmetric Henry reactions between various aldehydes 3 and CH(3)NO(2)4. The catalysts achieved a high level of enantioselectivity; product

  功能性咪唑鎓离子液体已被开发为一类新型的多功能催化剂。制备C（2）对称咪唑标记双（恶唑啉）配体，并改变了配体的阴离子。基于新的配体和Cu（OAc）（2）.H（2）O的催化剂被应用于各种醛3和CH（3）NO（2）4之间的不对称亨利反应。催化剂实现了高水平的对映选择性。在MeOH中以94％ee获得产物（R）-5n。而且，该催化剂可以循环使用6次而不会明显降低活性或对映选择性。另外，进行了理论机理研究以解释对映选择性的起源。
• Versatile Supramolecular Copper(II) Complexes for Henry and Aza-Henry Reactions
  作者：Guoqi Zhang、Eiji Yashima、Wolf-D. Woggon

  DOI：10.1002/adsc.200900069

  日期：2009.6

  Abstractmagnified imageChiral supramolecular metal‐organic frameworks assembled from copper complexes catalyse Henry and aza‐Henry reactions of aromatic and aliphatic aldehydes and N‐protected aromatic imines in high yield and good to excellent enantioselectivity. Reactions can be performed in the absence of base in ethanol or water.
• Recyclable copper catalysts based on ionic-tagged C2-symmetric Indabox ligands and their application in asymmetric Henry reactions
  作者：Zhi-Huai Li、Zhi-Ming Zhou、Xiao-Yan Hao、Jun Zhang、Xiao Dong、Ying-Qiang Liu、Wen-Wen Sun、Dan Cao

  DOI：10.1016/j.apcata.2012.02.044

  日期：2012.5

  New imidazolium/pyrrolidinium-tagged Indabox ligands were designed and prepared. Catalysts based on these ligands with Cu(OAc)(2)center dot H2O were applied to the asymmetric Henry reaction using various aldehydes and CH3NO2, the products were obtained in high enantioselectivity. Specifically, (R)-1-(2-methoxylphenyl)-2-nitroethanol was obtained in 94% ee in MeOH. Furthermore, the catalyst based on 7 could be recycled at least 12 times by simple wash without an obvious loss of activity or enantioselectivity. This catalytic procedure demonstrated the potential for catalyst recyclability in the asymmetric Henry reaction. Additionally, a theoretical mechanistic study was conducted to explain the origin of the enantioselectivity. (C) 2012 Elsevier B.V. All rights reserved.