(2S)-2-[(4-methoxyphenyl)methyl]-3-methylbutanoic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2S)-2-[(4-methoxyphenyl)methyl]-3-methylbutanoic acid
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: RSOCRCPICFCVKS-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-2-(4-methoxybenzylidene)-3-methylbutanoic acid 在 5%-palladium/activated carbon 、 氢气 、 辛可尼丁 、 苄胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 23.0 ℃ 、101.33 kPa 条件下， 生成 (2S)-2-[(4-methoxyphenyl)methyl]-3-methylbutanoic acid 、 (2R)-2-[(4-methoxyphenyl)methyl]-3-methylbutanoic acid
  参考文献：
  名称：

  Structural requirements for substrate in highly enantioselective hydrogenation over the cinchonidine-modified Pd/C

  摘要：

  Relationship between substrate Structure and enantioselectivity is studied for the asymmetric hydrogenation of 42 different (E)-alpha, beta-disubstituted acrylic acids (propenoic acids) over cinchonidine-modified Pd/C. The beta-phenyl group is indispensable for high enantioselectivity of alpha-phenylcinnamic acid (2,3-diphenylpropenoic acid, 81% ee), and substitution on this group affects markedly the selectivity. The high ee up to 92% was achieved by the beta-p-alkoxyphenyl substitution, and the selectivity is ascribed mainly to stronger interaction of the substrate with the chiral modifier on the catalyst surface. In contrast, substitution on the alpha-phenyl group does not affect notably the enantioselectivity (80-82% ee) or even the alpha-phenyl group itself is not indispensable but replaceable with a properly bulky group for the high enantioselectivity, (C) 2008 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jcat.2008.11.022