(S)-3-(4-methoxyphenyl)-glutaric acid monomethyl ester | 865367-03-9

• 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 monomethyl ester
• 英文别名: (S)-5-methoxy-3-(4-methoxyphenyl)-5-oxopentanoic acid；(3S)-5-methoxy-3-(4-methoxyphenyl)-5-oxopentanoic acid
• CAS: 865367-03-9
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: DICNRKZNJNQFRP-JTQLQIEISA-N

物化性质

• 熔点：
  85 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  406.0±40.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 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：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-3-(4-methoxyphenyl)-glutaric acid monomethyl 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 195.0h， 生成 (S)-3-(4-methoxyphenyl)-glutaric acid monomethyl 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。
• Development of Bifunctional Thiourea Organocatalysts Derived from a Chloramphenicol Base Scaffold and their Use in the Enantioselective Alcoholysis of<i>meso</i>Cyclic Anhydrides
  作者：Lin-Jie Yan、Hai-Feng Wang、Wen-Xue Chen、Yuan Tao、Kai-Jun Jin、Fen-Er Chen

  DOI：10.1002/cctc.201600228

  日期：2016.7.6

  chloramphenicol‐base‐derived thiourea organocatalysts, (1S,2R)‐12 a–f and (1R,2R)‐15 a–c, and their use in the enantioselective alcoholysis of meso‐anhydrides are described. In particular, hemiesters afforded excellent enantioselectivities if low loadings of (1S,2R)‐12 a–f were used. Almost no enantioselectivities were achieved with the use of (1R,2R)‐15 a–c. This technique was used to synthesize (R)‐(−)‐baclofen

  新的氯霉素基硫脲有机催化剂（1 S，2 R）-12 a - f和（1 R，2 R）15 a - c的合成及其在介孔酸酐的对映选择性醇解中的应用描述。特别是，如果使用低负荷的（1 S，2 R）-12 a – f负载，半酯具有出色的对映选择性。使用（1 R，2 R）‐ 15 a – c几乎没有达到对映选择性。该技术用于合成（R）-（-）-baclofen。
• Novel amide-functionalized chloramphenicol base bifunctional organocatalysts for enantioselective alcoholysis of<i>meso</i>-cyclic anhydrides
  作者：Lingjun Xu、Shuwen Han、Linjie Yan、Haifeng Wang、Haihui Peng、Fener Chen

  DOI：10.3762/bjoc.14.19

  日期：——

  possessing a NH functionality at C-1 position as monodentate hydrogen bond donor were developed and evaluated for enantioselective organocatalytic alcoholysis of meso-cyclic anhydrides. These structural diversified organocatalysts were found to induce high enantioselectivity in alcoholysis of anhydrides and was successfully applied to the asymmetric synthesis of (S)-GABOB.

  研发了一系列新型的氯霉素基础酰胺有机催化剂，它们在C-1位置具有NH官能团作为单齿氢键供体，并评估了其对中环酸酐的对映选择性有机催化醇解作用。发现这些结构多样的有机催化剂在酸酐的醇解中诱导高对映选择性，并成功地用于（S）-GABOB的不对称合成。
• 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.