(S)-3-苯基戊二酸单乙酯 | 137654-26-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: (S)-3-苯基戊二酸单乙酯
• 中文别名: 戊二酸,3-苯基-,单乙基酯,(S)-
• 英文名称: (S)-3-phenylglutaric acid monoethyl ester
• 英文别名: (3S)-5-ethoxy-5-oxo-3-phenylpentanoic acid
• CAS: 137654-26-3
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: YRTMKJSCLUJGPA-NSHDSACASA-N

物化性质

• 熔点：
  58-59 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  374.7±30.0 °C(Predicted)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 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-苯基戊二酸单乙酯 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 (4R)-4-phenyltetrahydro-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-苯基戊二酸 在 Amano PS-C immobilized 、 乙酰氯 作用下， 以 异丙醚 为溶剂， 反应 22.0h， 生成 (S)-3-苯基戊二酸单乙酯
  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

• Synthesis of Chiral Fluorides by Sequential Organocatalyzed Desymmetrization of Glutaric Anhydrides and Photoredox-Catalyzed Decarboxylic Fluorination
  作者：Shouyun Yu、Jia-Jia Zhao

  DOI：10.1055/s-0040-1707295

  日期：2021.3

  We have developed an efficient method for the preparation of chiral fluorinated compounds by sequential organocatalyzed desymmetrization of 3-substituted glutaric anhydrides and photoredox-catalyzed decarboxylic fluorination. Chiral fluorides can be prepared in yields of up to 58% and with excellent enantioselectivities of up to 98% ee.

  摘要：我们已经开发了一种高效的方法，通过顺序有机催化去对称化3-取代戊二酸酐和光还原催化脱羧氟化反应制备手性氟化合物。手性氟化物可以以高达58%的产率制备，并且具有高达98% ee的优异对映选择性。
• Chiral 2-Methyl-2-phenyl-1,3-oxazine-4,6-diones. Novel Building Blocks for the Synthesis of Enantiomerically Pure Compounds
  作者：Masayuki Sato、Noritaka Kitazawa、Shinya Nagashima、Kazuya Kano、Chikara Kaneko

  DOI：10.1246/cl.1992.485

  日期：1992.3

  Synthesis and optical resolution of (Z)-5-benzylidene as well as 5-alkyl derivatives of the title compounds have been accomplished. The Diels-Alder reaction of the former with ketene diethylacetal and base-mediated methylation of the latters were found to proceed preferencially from the same side of 2-methyl group of the oxazinedione rings. The reason for this selectivity is proposed.

  (Z)-5-亚苄基以及标题化合物的5-烷基衍生物的合成和光学拆分已经完成。发现前者与乙烯酮二乙缩醛的狄尔斯-阿尔德反应和后者的碱介导的甲基化优选从恶嗪二酮环的2-甲基的同一侧进行。提出了这种选择性的原因。
• 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.
• One-pot enzymatic desymmetrization and Ugi MCR
  作者：Anna Fryszkowska、Jadwiga Frelek、Ryszard Ostaszewski

  DOI：10.1016/j.tet.2005.04.032

  日期：2005.6

  A new approach to the synthesis of chiral peptidomimetics is reported. It combines an enzymatic desymmetrization of 3-phenylglutaric anhydrides with a subsequent Ugi multi-component reaction in a one-pot, two-step procedure. NMR and CD spectroscopy was used to assign the configurations of obtained products. Our synthetic method is very efficient and it can easily be extended to other types of multi-component reactions and can be used for the preparation of chiral peptidomimetic libraries. (c) 2005 Elsevier Ltd. All rights reserved.
• Chiral spirocyclic (Z)-5-arylmethylene-1,3-oxazine-4,6-diones, new chiral heterodienes
  作者：Masayuki Sato、Noritaka Kitazawa、Shinya Nagashima、Chikara Kaneko、Naoko Inoue、Toshio Furuya

  DOI：10.1016/s0040-4020(01)89729-5

  日期：1991.8

  A series of (Z)-5-arylmethlene-1,3-oxazine-4,6-diones was synthesized in enantiomerically pure form and found to serve as the attractive alternatives of 6-arylmethylene-1,4-oxazepane-5,7-diones.