diethyl 2-ethyl-2-m-nitrobenzylmalonate | 118688-45-2

• 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: diethyl 2-ethyl-2-m-nitrobenzylmalonate
• 英文别名: Diethyl ethyl[(3-nitrophenyl)methyl]propanedioate；diethyl 2-ethyl-2-[(3-nitrophenyl)methyl]propanedioate
• CAS: 118688-45-2
• 化学式: C₁₆H₂₁NO₆
• 分子量: 323.346
• InChiKey: DGQFVVYOSMGPIT-UHFFFAOYSA-N

物化性质

• 沸点：
  423.9±30.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 2-ethyl-2-m-nitrobenzylmalonate 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 硫酸 、 氢气 、 亚膦酸 、 sodium nitrite 作用下， 以 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 100.0h， 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：

  乙基丙二酸二乙酯 、 间硝基氯化苄 在 sodium hydride 作用下， 生成 diethyl 2-ethyl-2-m-nitrobenzylmalonate
  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

• PALECEK, JAROSLAV;PIS, JAROSLAV;LONDYN, MIROSLAV;BOROVICKA, MILOS;LUKAC, +
  作者：PALECEK, JAROSLAV、PIS, JAROSLAV、LONDYN, MIROSLAV、BOROVICKA, MILOS、LUKAC, +

  DOI：——

  日期：——