(S)-3-(3,4-dichlorophenyl)-glutaric acid monoethyl ester | 289639-45-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (S)-3-(3,4-dichlorophenyl)-glutaric acid monoethyl ester
• 英文别名: (S)-ethyl 3-(3',4'-dichlorophenyl)glutarate；(s)-3-(3,4-Dichlorophenyl)-5-ethoxy-5-oxopentanoic acid；(3S)-3-(3,4-dichlorophenyl)-5-ethoxy-5-oxopentanoic acid
• CAS: 289639-45-8
• 化学式: C₁₃H₁₄Cl₂O₄
• 分子量: 305.158
• InChiKey: FFKOTDLHQANJGE-VIFPVBQESA-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：

  (S)-3-(3,4-dichlorophenyl)-glutaric acid monoethyl ester 在 锂硼氢 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成
  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：

  diethyl 3-(3',4'-dichlorophenyl)glutarate 在 sodium hydroxide 、 immobilized lipase B (Candida antarctica, Chirazyme L-2) 作用下， 以 phosphate buffer 为溶剂， 反应 43.0h， 以82.1%的产率得到(S)-3-(3,4-dichlorophenyl)-glutaric acid monoethyl ester
  参考文献：
  名称：

  Enzymatic Hydrolysis of a Prochiral 3-Substituted Glutarate Ester, an Intermediate in the Synthesis of an NK1/NK2 Dual Antagonist

  摘要：

  An enzymatic process for desymmetrization of the prochiral diethyl 3-[3',4'-dichlorophenyl]-glutarate, 1, an intermediate in the synthesis of a series of neurokinin (NK) receptor antagonists, has been developed and scaled up. The transformation catalyzed by Candida antarctica lipase B in either the free or the immobilized form was carried out at 100 g/L of substrate and proceeded with an average conversion of 97%. In the pilot plant, the process produced 200 kg of 2 in 3 batches with cc > 99% and an average isolated yield of 80%. The immobilized enzyme preparation was particularly effective, achieving over 70,000 enzyme turnovers per batch.

  DOI：

  10.1002/1615-4169(200108)343:6/7<744::aid-adsc744>3.3.co;2-5

文献信息

• Studies on enzymatic synthesis of chiral non-racemic 3-arylglutaric acid monoesters
  作者：Anna Fryszkowska、Marta Komar、Dominik Koszelewski、Ryszard Ostaszewski

  DOI：10.1016/j.tetasy.2006.03.002

  日期：2006.3

  The enantioselective enzymatic desymmetrization (EED) of various 3-arylglutaric anhydrides I with alcohols in organic media has been studied. The effect of the solvent on the stereochemical outcome of the reaction was investigated in detail. The amount of biocatalyst was optimized, and the possibility of its re-use was tested. The first example of the EED of 3-substituted glutaric anhydrides with esters as nucleophiles is reported. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.
• Enzymatic Hydrolysis of a Prochiral 3-Substituted Glutarate Ester, an Intermediate in the Synthesis of an NK1/NK2 Dual Antagonist
  作者：Michael J. Homann、Robert Vail、Brian Morgan、Vijay Sabesan、Cliff Levy、David R. Dodds、Aleksey Zaks

  DOI：10.1002/1615-4169(200108)343:6/7<744::aid-adsc744>3.3.co;2-5

  日期：2001.8

  An enzymatic process for desymmetrization of the prochiral diethyl 3-[3',4'-dichlorophenyl]-glutarate, 1, an intermediate in the synthesis of a series of neurokinin (NK) receptor antagonists, has been developed and scaled up. The transformation catalyzed by Candida antarctica lipase B in either the free or the immobilized form was carried out at 100 g/L of substrate and proceeded with an average conversion of 97%. In the pilot plant, the process produced 200 kg of 2 in 3 batches with cc > 99% and an average isolated yield of 80%. The immobilized enzyme preparation was particularly effective, achieving over 70,000 enzyme turnovers per batch.