methyl 2,4-dinitro-3-phenylbutanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2,4-dinitro-3-phenylbutanoate
• 英文别名: Methyl 2,4-dinitro-3-phenylbutanoate
• 化学式: C₁₁H₁₂N₂O₆
• 分子量: 268.226
• InChiKey: OWRIQCTWBBZUEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  反式硝基苯乙烯 、 硝基乙酸甲酯 在 三乙胺 作用下， 以 正己烷 为溶剂， 反应 2.0h， 以66%的产率得到methyl 2,4-dinitro-3-phenylbutanoate
  参考文献：
  名称：

  Synthesis of Aliphatic 1,3-Dinitro Compounds

  摘要：

  在催化量的三乙胺或碳酸钾存在下，原生脂肪族硝基化合物与原生或仲生 δ-硝基烯烃发生反应，可生成收率很高的 1,3-二硝基化合物。

  DOI：

  10.1055/s-1996-4150

文献信息

• Investigation of lipase-catalyzed Michael-type carbon–carbon bond formations
  作者：Gernot A. Strohmeier、Tanja Sović、Georg Steinkellner、Franz S. Hartner、Aleksandra Andryushkova、Thomas Purkarthofer、Anton Glieder、Karl Gruber、Herfried Griengl

  DOI：10.1016/j.tet.2009.05.042

  日期：2009.7

  Conjugate additions of carbon nucleophiles to appropriate acceptor molecules were investigated with respect to the synthetic potential and stereochemistry of the products. Reactions of short-chain alpha,beta-unsaturated ketones and mono-substituted nitroalkenes with CH-acidic carboxylic ester derivatives were catalyzed by various immobilized lipases. Using methyl nitroacelate complete conversion with methyl vinyl ketone and trans-beta-nitrostyrene was obtained. The reactions proceeded without enantioselectivity. Evidence for enzyme catalysis is provided by the observation that after denaturation of Candida antarctica lipase B or inhibition no reaction took place. Docking studies with the chiral addition product rnethyl 2-methyl-2-nitro-5-oxoliexatioate did not reveal any specific binding mode for this reaction product, which would have been the requirement for stereoselective additions. These results support the experimental findings that the conjugate addition takes place without enantiopreference. (C) 2009 Elsevier Ltd. All rights reserved.