(2S)-2-(4-methoxyphenyl)-3-[4-(3-phenylpropoxy)phenyl]propanoic acid | 1142935-19-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2S)-2-(4-methoxyphenyl)-3-[4-(3-phenylpropoxy)phenyl]propanoic acid
• CAS: 1142935-19-0
• 化学式: C₂₅H₂₆O₄
• 分子量: 390.479
• InChiKey: WELJGSCNRMRLNM-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  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)-3-[4-(3-phenylpropoxy)phenyl]propanoic 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

文献信息

• Is amine addition vital for highly enantioselective hydrogenation of α,β-unsaturated carboxylic acid over cinchonidine-modified palladium?
  作者：Tae Yeon Kim、Takashi Sugimura

  DOI：10.1016/j.molcata.2010.05.013

  日期：2010.7

  Benzylamine (BA) is a commonly employed additive for the hydrogenation of α,β-unsaturated acids over the cinchonidine-modified palladium catalyst, but the BA addition effects largely depend on the reaction solvent. In toluene, BA is not required to obtain the high enantioselectivity. Quicker desorption of the product due to weaker acidity in toluene than in a commonly used wet dioxane reasonably explains

  苄胺（BA）是在辛可尼定改性的钯催化剂上氢化α，β-不饱和酸的常用添加剂，但BA的添加效果很大程度上取决于反应溶剂。在甲苯中，不需要BA来获得高对映选择性。由于甲苯中的酸度比通常使用的湿式二恶烷弱，因此产物的解吸速度更快，这可以合理地解释其动力学性质和产物的选择性。