(3S)-5-丁氧基-5-氧代-3-苯基戊酸 | 865366-96-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 中文名称: (3S)-5-丁氧基-5-氧代-3-苯基戊酸
• 英文名称: (S)-3-phenylglutaric acid monobutyl ester
• 英文别名: (3S)-5-Butoxy-5-oxo-3-phenylpentanoic acid
• CAS: 865366-96-7
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: OJKPOCZYELBGMU-ZDUSSCGKSA-N

物化性质

• 熔点：
  41-43 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  400.4±33.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  (3S)-5-丁氧基-5-氧代-3-苯基戊酸 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 Novozym 435 、 乙酰氯 作用下， 以 异丙醚 为溶剂， 反应 411.0h， 生成 (3S)-5-丁氧基-5-氧代-3-苯基戊酸
  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。
• 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.