(R)-1-(2,4-dimethoxyphenyl)-2-nitroethanol | 1502715-37-8

• 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: (R)-1-(2,4-dimethoxyphenyl)-2-nitroethanol
• 英文别名: 2-nitro-1-(2,4-dimethoxyphenyl)ethanol；1-(2,4-dimethoxyphenyl)-2-nitroethanol；(1R)-1-(2,4-dimethoxyphenyl)-2-nitroethanol
• CAS: 1502715-37-8
• 化学式: C₁₀H₁₃NO₅
• 分子量: 227.217
• InChiKey: XVIGKRSVEFCTSG-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  硝基甲烷 、 2,4-二甲氧基苯甲醛 在 Arabidopsis thaliana hydroxynitrile lyase Y₁₄M variant 作用下， 以 aq. phosphate buffer 、 乙酸丁酯 为溶剂， 以98%的产率得到
  参考文献：
  名称：

  用于混杂不对称亨利反应的羟基腈裂合酶工程，具有增强的转化率、对映选择性和催化效率

  摘要：

  拟南芥羟基腈裂解酶 ( At HNL) 工程已发现变体，其对不对称 Henry 反应的催化效率比野生型提高了 12 倍。At HNL 变体在从相应的醛合成 13 种不同的 ( R )-β-硝基醇时表现出优异的对映选择性（高达 >99%）和更高的转化率。使用 Y14M/F179W 的细胞裂解物，我们证明了 ( R )-1-(4-甲氧基苯基)-2-硝基乙醇（一种 Tembamide 手性中间体）的制备规模合成，其 ee 大于 99%，产率 52%。

  DOI：

  10.1039/d3cc02837b

文献信息

• <i>C</i> ₁ -Symmetric 1,2-Diaminobicyclo[2.2.2]octane Ligands in Copper-Catalyzed Asymmetric Henry Reaction: Catalyst Development and DFT Studies
  作者：Pierre Milbeo、Laure Moulat、Claude Didierjean、Emmanuel Aubert、Jean Martinez、Monique Calmès

  DOI：10.1002/ejoc.201701452

  日期：2018.1.17

  2-diaminobicyclo[2.2.2]octane ligand L10 with Cu(OAc)2 proved to be the most effective for the asymmetric Henry reaction of nitromethane with various aldehydes, providing b-nitroalcohols in moderate to good yields, and enantioselectivity (up to 86%). In an attempt to rationalize the factors that control enantiodifferentiation, the most stable geometries of this C1-symmetric bicyclic copper ligand complex, as well

  已经合成了衍生自 (R)-1,2-二氨基双环 [2.2.2] 辛烷支架的新型手性四齿和双齿配体，并研究了配体 N,N'-取代基对其相应铜 (II) 催化活性的影响) 配合物对硝基醛醇反应进行了研究。其中，(R)-N,N'-双(1-萘基甲基)-1,2-二氨基双环[2.2.2]辛烷配体L10与Cu(OAc)2相互作用原位生成的配合物证明对硝基甲烷与各种醛的不对称亨利反应最有效，以中等至良好的产率和对映选择性（高达 86%）提供 b-硝基醇。为了使控制对映分化的因素合理化，这种 C1 对称双环铜配体复合物的最稳定几何结构，
• Synthesis and computation of diastereomeric phenanthroline–quinine ligands and their application in asymmetric Henry reaction
  作者：Lili Zhang、Hao Wu、Zhongyue Yang、Xiufang Xu、Haitao Zhao、Yaodong Huang、Yongmei Wang

  DOI：10.1016/j.tet.2013.10.010

  日期：2013.12

  A class of chiral ligands has been developed by combining phenanthroline with quinine in a one-step method that does not require resolution. The synthesized three ligands were then coordinated with Cu-(II) and the performance of the resultant chiral catalysts in the asymmetric Henry reaction was evaluated. Moderate to good yields (up to 86%) with high enantioselectivities (up to 99% ee) were observed in the reactions catalyzed by one of the three catalysts. Theoretical calculations were performed to analyze the catalytic activities of the different Cu-(II)-ligand catalysts. Three different ligands were investigated and one ligand was found to adopt an unexpected five-coordinated mode; the second coordinated with two nitrogen atoms of phenanthroline to give a complex, which activated both substrates of Henry reaction; the third was unable to form a complex with Cu-(II). (C) 2013 Elsevier Ltd. All rights reserved.