3-(4-Fluorophenyl)-2-(2-methoxyphenyl)propanoic acid | 1017165-97-7

• 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: 3-(4-Fluorophenyl)-2-(2-methoxyphenyl)propanoic acid
• CAS: 1017165-97-7
• 化学式: C₁₆H₁₅FO₃
• 分子量: 274.292
• InChiKey: KTCCEYALKPVVCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 3-(4-Fluorophenyl)-2-(2-methoxyphenyl)propanoic acid 以 乙醚 为溶剂， 生成
  参考文献：
  名称：

  Reactions of chlorine substituted (E)-2,3-diphenylpropenoic acids over cinchonidine-modified Pd: Enantioselective hydrogenation versus hydrodechlorination

  摘要：

  The effect of the chlorine position on the C-Cl bond hydrogenolysis and the enantioselective hydrogenation of Cl substituted (E)-2,3-diphenylpropenoic acid derivatives has been studied over cinchonidine-modified Pd/Al2O3. In contrast to the fast hydrodechlorination of the beta-phenyl-para-Cl substituted acids the Cl on the alpha-phenyl ring was barely hydrogenolized. These observations were interpreted by the different arrangements of the two phenyl rings on the surface, with the alpha- and beta-phenyl rings adsorbed tilted and parallel, respectively. The results confirmed the beneficial effect of the alpha-phenyl-ortho-substituents on the chiral discrimination, thus the 2,3-diphenylpropionic acids substituted by Cl on the alpha-phenyl ring could be prepared in good yields and optical purities. The conclusions were used for the rational design of an acid, i.e. (E)-2-(2-methoxyphenyl)-3-(3,4-difluorophenyl)propenoic acid, which afforded the best optical purity (ee up to 95% at 295 K) described until now in this heterogeneous system. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2010.09.013
• 作为产物：
  描述：

  4-fluoro-2'-methoxyphenylcinnamic acid 在 palladium on activated charcoal 、 氢气 、 cinchonidine 、 苄胺 作用下， 以 1,4-二氧六环 为溶剂， 22.84 ℃ 、1.0 MPa 条件下， 以100%的产率得到3-(4-Fluorophenyl)-2-(2-methoxyphenyl)propanoic acid
  参考文献：
  名称：

  Anomalous Ligand Acceleration on Cinchona-modified Pd/C during Asymmetric Hydrogenation of Properly Substituted Phenylcinnamic Acid

  摘要：

  在 Pd/C 上氢化 4,4′-二甲氧基-α-苯基肉桂酸时，使用金鸡纳啶改性剂会产生很大的配体加速效应；与未改性 Pd/C 上的反应速率相比，氢化速率提高了 370%，对映体过量（ee）达到 91%。另一种优质底物 4-氟-2′-甲氧基苯基肉桂酸的ee值也高达 92%；但使用这种改性剂时，反应速率仅提高到 230%。根据反应速率加快程度的差异，对每种底物的 eemax 进行了分析。

  DOI：

  10.1246/cl.130245

文献信息

• Kinetic Analysis of Enantioselective Hydrogenation of 2,3-(<i>E</i>)-Diarylpropenoic Acids over a Chiral Cinchona Alkaloid-Modified Pd/C Catalyst
  作者：Bokeun Kim、Makoto Nakatsuji、Takuya Mameda、Takeshi Kubota、Morifumi Fujita、Takashi Sugimura、Yasuaki Okamoto

  DOI：10.1246/bcsj.20190290

  日期：2020.1.15

  Enantioselective hydrogenations of α,β-unsaturated carboxylic acids over cinchona alkaloid-modified Pd metal heterogeneous catalysts have received considerable attention because of scientific impor...

  金鸡纳生物碱修饰的钯金属多相催化剂对α,β-不饱和羧酸的对映选择性加氢由于科学上的重要...
• Reactions of chlorine substituted (E)-2,3-diphenylpropenoic acids over cinchonidine-modified Pd: Enantioselective hydrogenation versus hydrodechlorination
  作者：György Szőllősi、Beáta Hermán、Erika Szabados、Ferenc Fülöp、Mihály Bartók

  DOI：10.1016/j.molcata.2010.09.013

  日期：2010.12

  The effect of the chlorine position on the C-Cl bond hydrogenolysis and the enantioselective hydrogenation of Cl substituted (E)-2,3-diphenylpropenoic acid derivatives has been studied over cinchonidine-modified Pd/Al2O3. In contrast to the fast hydrodechlorination of the beta-phenyl-para-Cl substituted acids the Cl on the alpha-phenyl ring was barely hydrogenolized. These observations were interpreted by the different arrangements of the two phenyl rings on the surface, with the alpha- and beta-phenyl rings adsorbed tilted and parallel, respectively. The results confirmed the beneficial effect of the alpha-phenyl-ortho-substituents on the chiral discrimination, thus the 2,3-diphenylpropionic acids substituted by Cl on the alpha-phenyl ring could be prepared in good yields and optical purities. The conclusions were used for the rational design of an acid, i.e. (E)-2-(2-methoxyphenyl)-3-(3,4-difluorophenyl)propenoic acid, which afforded the best optical purity (ee up to 95% at 295 K) described until now in this heterogeneous system. (C) 2010 Elsevier B.V. All rights reserved.
• Anomalous Ligand Acceleration on Cinchona-modified Pd/C during Asymmetric Hydrogenation of Properly Substituted Phenylcinnamic Acid
  作者：Hiroyuki Ogawa、Takuya Mameda、Tomonori Misaki、Yasuaki Okamoto、Takashi Sugimura

  DOI：10.1246/cl.130245

  日期：2013.8.5

  The hydrogenation of 4,4′-dimethoxy-α-phenylcinnamic acid over Pd/C showed a large ligand acceleration effect when a cinchonidine modifier was used; the hydrogen rate increased to 370% relative to the reaction rate on unmodified Pd/C and resulted in a 91% enantiomeric excess (ee). Another good substrate, 4-fluoro-2′-methoxyphenylcinnamic acid, also resulted in a high ee value of 92%; however, the rate increased only to 230% when this modifier was used. On the basis of the difference in the degree to which the reaction rate was accelerated, the eemax for each substrate was analyzed.

  在 Pd/C 上氢化 4,4′-二甲氧基-α-苯基肉桂酸时，使用金鸡纳啶改性剂会产生很大的配体加速效应；与未改性 Pd/C 上的反应速率相比，氢化速率提高了 370%，对映体过量（ee）达到 91%。另一种优质底物 4-氟-2′-甲氧基苯基肉桂酸的ee值也高达 92%；但使用这种改性剂时，反应速率仅提高到 230%。根据反应速率加快程度的差异，对每种底物的 eemax 进行了分析。