(S)-3-(4-methoxyphenyl)-glutaric acid monobenzyl ester | 865367-05-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (S)-3-(4-methoxyphenyl)-glutaric acid monobenzyl ester
• 英文别名: 5-(benzyloxy)-3-(4-methyoxyphenyl)-5-oxopentanoic acid
• CAS: 865367-05-1
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: DTSCWNQLFJRNQI-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-3-(4-methoxyphenyl)-glutaric acid monobenzyl 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：

  3-(4-甲氧基苯基)戊二酸 在 Novozym 435 、 乙酰氯 作用下， 以 异丙醚 为溶剂， 反应 795.0h， 生成 (S)-3-(4-methoxyphenyl)-glutaric acid monobenzyl 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

• Organocatalyzed Step-Growth Polymerization through Desymmetrization of Cyclic Anhydrides: Synthesis of Chiral Polyesters
  作者：Anthony Martin、Frédéric Robert、Daniel Taton、Henri Cramail、Jean-Marc Vincent、Yannick Landais

  DOI：10.1002/chem.201402373

  日期：2014.9.8

  moderate degrees of polymerization were attained through this step‐growth polymerization. The enantioselectivity of the process was evaluated by using chiral HPLC analysis of the bis‐lactones resulting from a controlled chemoselective degradation of the polyesters. The best stereocontrol was reached for oligomers formed from bis‐anhydride and diol monomers bearing rigid aromatic spacers between the reactive

  金鸡纳生物碱催化前手性双酸酐与二醇的聚合反应可提供高收率和高水平立体控制性的手性聚酯。聚酯的结构由1 H和13确定进行13 C NMR分析，而尺寸排阻色谱法（SEC）和MALDI-TOF质谱法均可估算其大小，这表明通过这种逐步增长的聚合反应可达到中等程度的聚合度。该方法的对映选择性是通过对聚酯化学控制选择性降解产生的双内酯进行手性HPLC分析来评估的。对于由双酸酐和二醇单体形成的低聚物，在反应性官能团之间带有刚性芳族间隔基，可获得最佳的立体控制。在这种情况下，平均对映选择性与在类似酸酐的简单酸酐开环过程中观察到的相当。相反，在反应性实体之间使用更灵活的间隔物通常导致较低的立体控制水平。