(S)-2-nitro-1-(3,4,5-trimethoxyphenyl)ethanol | 1186497-23-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-2-nitro-1-(3,4,5-trimethoxyphenyl)ethanol
• 英文别名: 1-(3,4,5-trimethoxyphenyl)-2-nitroethanol；(1S)-2-nitro-1-(3,4,5-trimethoxyphenyl)ethanol
• CAS: 1186497-23-3
• 化学式: C₁₁H₁₅NO₆
• 分子量: 257.243
• InChiKey: STKSTSQRUAJJQR-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.02
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  91.06
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 在 hydroxynitrile lyase from Arabidopsis thaliana 、 barium(II) hydroxide 作用下， 以 aq. phosphate buffer 、 氘代甲苯 、 水 为溶剂， 反应 3.0h， 生成 (S)-2-nitro-1-(3,4,5-trimethoxyphenyl)ethanol 、 2-nitro-1-(3,4,5-trimethoxyphenyl)ethanol
  参考文献：
  名称：

  通过R选择性羟基腈裂解酶的对映选择性C-C键裂解生产（S）-β-硝基醇

  摘要：

  裂解要比合成快：在HNL催化的立体选择性逆亨利裂解中，外消旋β-硝基醇 通过动力学拆分产生相应的S对映体，在3–7 h内具有高达99％ee和47％的转化率。这种方法拓宽了At HNL在适当的底物上合成（R）-和（S）-β-硝基醇的应用范围。

  DOI：

  10.1002/cbic.201800416

文献信息

• Enantioselective Henry reaction catalyzed by C2-symmetric chiral diamine–copper(II) complex
  作者：Sermadurai Selvakumar、Dhanasekaran Sivasankaran、Vinod K. Singh

  DOI：10.1039/b904254g

  日期：——

  A copper(II) complex of C2-symmetric diamine has been proved to be an efficient catalyst for the enantioselective Henry reaction between nitroalkanes and various aldehydes to provide β-hydroxy nitroalkanes in high yields (up to 97%), moderate diastereoselectivities (up to 71:29) and excellent enantiomeric excesses (up to 96%). The chiral nitroaldol adduct obtained has been further converted into chiral

  事实证明，C 2对称二胺的铜（II）络合物是硝基链烷烃与各种醛之间对映选择性亨利反应的有效催化剂，以高产率（高达97％），中等非对映选择性（高达90％以上）提供β-羟基硝基链烷烃。至71:29）和出色的对映体过量（高达96％）。所获得的手性硝基醛醇加合物在几个步骤中已进一步转化为手性氮丙啶。
• The first 4,4′-imidazolium-tagged C₂-symmetric bis(oxazolines): application in the asymmetric Henry reaction
  作者：Li-Wei Tang、Xiao Dong、Zhi-Ming Zhou、Ying-Qiang Liu、Li Dai、Man Zhang

  DOI：10.1039/c4ra14028a

  日期：——

  Highly efficient and recyclable imidazolium-tagged bis(oxazolines), with an imidazolium tagged onto the 4,4′-position of the box, have been designed and prepared for the first time. They have been synthesized from dimethylmalonic acid and used as chiral ligands in the copper(II)-catalyzed classic asymmetric Henry reaction between aldehydes and nitromethane. A systematic analysis of the anions showed

  首次设计并制备了带有咪唑鎓标签的高效，可回收的咪唑鎓标签双（恶唑啉）。它们是由二甲基丙二酸合成的，并用作铜（II）催化的醛与硝基甲烷之间经典的不对称亨利反应中的手性配体。对阴离子的系统分析表明，最好的配体是中等大小的一种。该催化剂具有很高的活性和对映选择性，并具有良好的可回收性，即产物（R）-11k在MeOH中以94％ee达到目标值。而且，该催化剂成功地循环了六次，而活性或对映选择性没有明显损失。最后，进行了理论机理研究，以解释对映选择性的起源以及阴离子的大小如何影响反应。
• Noncovalent Immobilization of Ionic-tagged Box-Cu(OAc)₂ Complex and Its Application in Asymmetric Henry Reaction
  作者：Zhi-Huai Li、Zhi-Ming Zhou、Xiao-Yan Hao、Jun Zhang、Xiao Dong、Ying-Qiang Liu

  DOI：10.1002/chir.22104

  日期：2012.12

  Immobilized Cu(OAc)2‐bis(oxazolines) via hydrogen bonding by SBA‐15 was applied to asymmetric Henry reaction, and good enantioselectivities were obtained (up to 83% ee) between 2‐methoxybenzaldehyde and CH3NO2 in isopropyl alcohol (iPrOH). The catalyst could be reused seven times without any obvious loss in enantioselectivity. For the first time, this facile and clean immobilization method is applied

  将SBA-15通过氢键固定的Cu（OAc）2-双（恶唑啉）用于不对称亨利反应，并在异丙醇（2-甲氧基苯甲醛）和CH 3 NO 2之间获得了良好的对映选择性（最高83％ee）。我PrOH）。该催化剂可以重复使用七次而对映选择性没有任何明显的损失。首次将这种简便，清洁的固定化方法应用于双（恶唑啉）配合物的使用。手性24：1092-1095，2012。分级为4 +©2012 Wiley Periodicals，Inc.
• 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。
• 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.