(+/-)-3-m-nitrophenyl-2-ethylpropionic acid | 138809-58-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (+/-)-3-m-nitrophenyl-2-ethylpropionic acid
• 英文别名: 2-(3-Nitrobenzyl)butanoic acid；2-[(3-nitrophenyl)methyl]butanoic acid
• CAS: 138809-58-2
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: WZRVLOGQNMKHFK-UHFFFAOYSA-N

物化性质

• 沸点：
  388.7±17.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+/-)-3-m-nitrophenyl-2-ethylpropionic acid 在 palladium on activated charcoal 盐酸 、 硫酸 、 氢气 、 亚膦酸 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 (R)-(-)-methyl 3-phenyl-2-ethylpropionate
  参考文献：
  名称：

  Chemoenzymatic synthesis of the enantiomers of iopanoic acid

  摘要：

  The two enantiomers of Iopanoic acid 1 were prepared in enantiomeric excess higher than 90% by enzyme-catalyzed hydrolysis of precursors (+/-)-2a and (+/-)-3a, followed by standard chemical transformations. Among the tested enzymes, chymotrypsin and Lipase PS proved to be the most selective catalysts. The stereochemical outcome of the lipase-catalyzed hydrolyses of esters (+/-)-2a-d is strictly dependent upon both the size of the alkyl group attached to the chiral center and the substituent in the aromatic ring. The enantioselectivity of the reactions was evaluated by chiral HPLC and the configurations of the new products were assigned by chemical correlations.

  DOI：

  10.1016/s0957-4166(00)86152-2
• 作为产物：
  描述：

  2-ethyl-2-m-nitrobenzylmalonic acid 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (+/-)-3-m-nitrophenyl-2-ethylpropionic acid
  参考文献：
  名称：

  Chemoenzymatic synthesis of the enantiomers of iopanoic acid

  摘要：

  The two enantiomers of Iopanoic acid 1 were prepared in enantiomeric excess higher than 90% by enzyme-catalyzed hydrolysis of precursors (+/-)-2a and (+/-)-3a, followed by standard chemical transformations. Among the tested enzymes, chymotrypsin and Lipase PS proved to be the most selective catalysts. The stereochemical outcome of the lipase-catalyzed hydrolyses of esters (+/-)-2a-d is strictly dependent upon both the size of the alkyl group attached to the chiral center and the substituent in the aromatic ring. The enantioselectivity of the reactions was evaluated by chiral HPLC and the configurations of the new products were assigned by chemical correlations.

  DOI：

  10.1016/s0957-4166(00)86152-2

文献信息

• Substrate scope and synthetic applications of the enantioselective reduction of α-alkyl-β-arylenones mediated by Old Yellow Enzymes
  作者：Elisabetta Brenna、Sara Lucia Cosi、Erica Elisa Ferrandi、Francesco G. Gatti、Daniela Monti、Fabio Parmeggiani、Alessandro Sacchetti

  DOI：10.1039/c3ob40076j

  日期：——

  The ene-reductases mediated bioreduction of a selection of open-chain α-alkyl-β-aryl enones afforded the corresponding saturated α-chiral ketones in high yield and optical purity in several cases. The stereo-electronic requirements of the reaction have been investigated, considering the nature and location of substituents on the aromatic ring as well as the steric hindrance at the α-position and adjacent

  在一些情况下，烯还原酶介导的对选择的开链α-烷基-β-芳基烯酮的生物还原以高产率和光学纯度提供了相应的饱和α-手性酮。考虑到芳环上取代基的性质和位置以及在α位和羰基官能团附近的位阻，已研究了反应的立体电子要求。所考虑的一般考虑因素使我们能够指导设计用于将来的制备应用中的烯键还原酶的底物的α，β-不饱和酮的设计。来自酵母菌的高度同源的烯还原酶中基于酶和基于底物的立体控制之间的正交性的有趣情况物种（OYE1-3）已经通过计算机对接研究得到了报道和合理化。此外，为了证实该反应的合成通用性，如（2'生物活性化合物的关键手性前- [R）-stenusines和（小号获得）-iopanoic酸。非常强大的实验方案使我们能够以简单的后处理和无需色谱纯化的步骤，以定量收率在制备规模上进行反应。