3-(3,4-dichlorophenyl)-glutaric acid monoethyl ester | 181880-25-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-(3,4-dichlorophenyl)-glutaric acid monoethyl ester
• 英文别名: ethyl 4-carboxy-3-(3,4-dichlorophenyl)butanoate；3-(3,4-dichlorophenyl)-5-ethoxy-5-oxopentanoic acid
• CAS: 181880-25-1
• 化学式: C₁₃H₁₄Cl₂O₄
• 分子量: 305.158
• InChiKey: FFKOTDLHQANJGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3,4-dichlorophenyl)-glutaric acid monoethyl ester 在 锂硼氢 、 potassium tert-butylate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 生成 4-(3,4-dichlorophenyl)tetrahydro-2H-pyran-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-(3,4-二氯苯基)戊二酸 在 吡啶 、 乙酰氯 作用下， 反应 5.0h， 生成 3-(3,4-dichlorophenyl)-glutaric acid monoethyl ester
  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

• 5-(4-SUBST.-PIPERIDINYL-1)-3-ARYL-PENTANOIC ACID DERIVATIVES AS TACHYKININ RECEPTOR ANTAGONIST
  申请人：AstraZeneca AB

  公开号：EP0808303B1

  公开（公告）日：2001-06-20
• US6410306B1
  申请人：——

  公开号：US6410306B1

  公开（公告）日：2002-06-25
• [EN] 5-(4-SUBST.-PIPERIDINYL-1)-3-ARYL-PENTANOIC ACID DERIVATIVES AS TACHYKININ RECEPTOR ANTAGONIST<br/>[FR] DERIVES D'ACIDE 5-(4-SUBSTITUE-PIPERIDINYL-1)-3-ARYL-PENTANOIQUE UTILISES COMME ANTAGONISTES DES RECEPTEURS DE LA TACHYKININE
  申请人：ZENECA LIMITED

  公开号：WO1996024582A1

  公开（公告）日：1996-08-15

  (EN) Compounds of formula (I), wherein Q1, Q2, Q3 and Q4 have any of the meanings given in the specification, their N-oxided, and their pharmaceutically acceptable salts are nonpeptide antagonists of SP and NKA, useful for the treatment of asthma, etc. Also disclosed are pharmaceutical compositions, processes for preparing the compounds of formula (I) and intermediates.(FR) La présente invention concerne des composés représentés par la formule (I) dans laquelle Q1, Q2, Q3 et Q4 ont les significations données dans la description de l'invention, des N-oxydes ainsi que des sels pharmaceutiquement acceptables de ces composés, qui sont des antagonistes non peptidiques de SP et de la neurokinine A (NKA) et sont utiles pour le traitement de l'asthme, etc. L'invention se rapporte également à des compositions pharmaceutiques contenant les composés de la formule (I) ainsi qu'à des procédés de préparation de ces composés et de leurs intermédiaires.
• [EN] ENANTIOSELECTIVE ENZYMATIC HYDROLYSIS OF 3-SUBSTITUTED ESTERS OF GLUTARIC ACID<br/>[FR] HYDROLYSE ENZYMATIQUE ENANTIOSELECTIVE D'ESTERS 3-SUBSTITUE D'ACIDE GLUTARIQUE
  申请人：SCHERING CORP

  公开号：WO2000050628A1

  公开（公告）日：2000-08-31

  A process is provided for preparing an S-enantiomer compound having formula (IA) in enantiomeric excess, or an R-enantiomer compound having formula (IB) in enantiomeric excess, said process comprising hydrolyzing a compound having formula (II) with: (a) an enzyme capable of producing an enantiomeric excess of the S-enantiomer compound of formula (IA) of at least 70 %, or (b) an enzyme capable of producing an enantiomeric excess of the R-enantiomer compound of formula (IB) of at least 70 %, wherein R1 is selected from the group consisting of alkyl, aryl, aralkyl, cycloalkyl, or cycloalkylalkyl.