5-hydroxy-3-phenyl-valeric acid | 761366-49-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 5-hydroxy-3-phenyl-valeric acid
• 英文别名: 5-Hydroxy-3-phenyl-valeriansaeure；5-Hydroxy-3-phenylpentanoic acid
• CAS: 761366-49-8
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: WRTIFQXTQMEHDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-hydroxy-3-phenyl-valeric acid 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 生成 4-phenyltetrahydropyran-2-one
  参考文献：
  名称：

  Enzymatic desymmetrization of 3-arylglutaric acid anhydrides

  摘要：

  Optically active (R)- and (S)-3-arylglutaric acid monoesters 3 were synthesized in quantitative yields and good stereoselectivities by lipase-catalyzed desymmetrization of the corresponding 3-arylglutaric anhydrides 2 with alcohols. It was observed that the stereochemical outcome of the reaction was influenced by the substituents present on the aromatic ring. The influence of the enzyme, alcohol, and solvent was systematically examined. Absolute configurations of the monoesters 3 were assigned by chemical correlation to corresponding lactones 4. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.025
• 作为产物：
  描述：

  3-苯基戊二酸单乙酯 在 锂硼氢 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 5-hydroxy-3-phenyl-valeric acid
  参考文献：
  名称：

  Enzymatic desymmetrization of 3-arylglutaric acid anhydrides

  摘要：

  Optically active (R)- and (S)-3-arylglutaric acid monoesters 3 were synthesized in quantitative yields and good stereoselectivities by lipase-catalyzed desymmetrization of the corresponding 3-arylglutaric anhydrides 2 with alcohols. It was observed that the stereochemical outcome of the reaction was influenced by the substituents present on the aromatic ring. The influence of the enzyme, alcohol, and solvent was systematically examined. Absolute configurations of the monoesters 3 were assigned by chemical correlation to corresponding lactones 4. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.025

文献信息

• 2-Phenylcyclobutanecarboxylic Acid¹
  作者：ALFRED BURGER、ALFRED HOFSTETTER

  DOI：10.1021/jo01091a034

  日期：1959.9
• MACROCYCLIC AMINOPYRIDYL BETA-SECRETASE INHIBITORS FOR THE TREATMENT OF ALZHEIMER'S DISEASE
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP1817312B1

  公开（公告）日：2011-06-08
• US5830936A
  申请人：——

  公开号：US5830936A

  公开（公告）日：1998-11-03
• [EN] CATALYST BASED ON A BETA-SUBSTITUTED ESTER AND USE THEREOF IN A HYDROTREATMENT AND/OR HYDROCRACKING PROCESS<br/>[FR] CATALYSEUR A BASE D'UN ESTER BETA-SUBSTITUE ET SON UTILISATION DANS UN PROCEDE D'HYDROTRAITEMENT ET/OU D'HYDROCRAQUAGE
  申请人：IFP ENERGIES NOW

  公开号：WO2020002136A1

  公开（公告）日：2020-01-02

  L'invention a pour objet un catalyseur comprenant un support à base d'alumine ou de silice ou de silice-alumine, au moins un élément du groupe VIII, au moins un élément du groupe VIB, et au moins un composé organique de formule (I) dans laquelle R1 est un radical hydrocarboné comprenant de 1 à 12 atomes de carbone, R2, R3 et R4 sont choisis parmi un atome d'hydrogène et un radical hydrocarboné comprenant de 1 à 12 atomes de carbone, X est choisi parmi un atome d'oxygène ou un atome de soufre sauf lorsque Y représente un atome d'hydrogène X est alors un atome d'oxygène, et Y est choisi parmi un atome d'hydrogène, un radical hydrocarboné comprenant de 1 à 12 atomes de carbone, ou un motif –C(O)R5, R5 étant choisi parmi un atome d'hydrogène et un radical hydrocarboné comprenant de 1 à 12 atomes de carbone.
• Enzymatic desymmetrization of 3-arylglutaric acid anhydrides
  作者：Anna Fryszkowska、Marta Komar、Dominik Koszelewski、Ryszard Ostaszewski

  DOI：10.1016/j.tetasy.2005.06.025

  日期：2005.7

  Optically active (R)- and (S)-3-arylglutaric acid monoesters 3 were synthesized in quantitative yields and good stereoselectivities by lipase-catalyzed desymmetrization of the corresponding 3-arylglutaric anhydrides 2 with alcohols. It was observed that the stereochemical outcome of the reaction was influenced by the substituents present on the aromatic ring. The influence of the enzyme, alcohol, and solvent was systematically examined. Absolute configurations of the monoesters 3 were assigned by chemical correlation to corresponding lactones 4. (C) 2005 Elsevier Ltd. All rights reserved.