(S)-(+)-2-ethyl-3-(3-nitrophenyl)propionic acid | 138711-94-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (S)-(+)-2-ethyl-3-(3-nitrophenyl)propionic acid
• 英文别名: (2S)-2-[(3-nitrophenyl)methyl]butanoic acid
• CAS: 138711-94-1
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: WZRVLOGQNMKHFK-VIFPVBQESA-N

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

• 作为产物：
  描述：

  (+/-)-3-m-nitrophenyl-2-ethylpropionic acid 在 盐酸 、 potassium phosphate 作用下， 反应 120.0h， 生成 (S)-(+)-2-ethyl-3-(3-nitrophenyl)propionic 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

• Stereochemical Control in Microbial Reduction. XXVIII. Asymmetric Reduction of<i>α</i>,<i>β</i>-Unsaturated Ketones with Bakers’ Yeast
  作者：Yasushi Kawai、Kentarou Saitou、Kouichi Hida、Duc Hai Dao、Atsuyoshi Ohno

  DOI：10.1246/bcsj.69.2633

  日期：1996.9

  Bakers’ yeast reduction of α,β-unsaturated ketones affords optically active saturated ketones contaminated by allylic and saturated alcohols as minor components. Stereoselectivity of the reduction of carbon–carbon double bond strongly depends on the structure of β-aryl substituent. The bakers’ yeast reduction of β-phenyl enones gives saturated ketones in moderate stereoselectivity. Stereoselectivity

  面包师酵母对 α,β-不饱和酮的还原提供了被烯丙醇和饱和醇作为次要成分污染的旋光饱和酮。碳-碳双键还原的立体选择性很大程度上取决于β-芳基取代基的结构。面包师酵母对 β-苯烯酮的还原产生了中等立体选择性的饱和酮。立体选择性不会因对位取代而改变，而在邻位或间位引入取代基可显着提高立体选择性。氘标记实验表明，无论立体选择性的效率如何，碳-碳双键的酶促还原都伴随着氢的形式反式加成。得到的旋光酮转化为 (S)-碘潘酸的前体，