(R)-3-(3,4-dichlorophenyl)-glutaric acid monomethyl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (R)-3-(3,4-dichlorophenyl)-glutaric acid monomethyl ester
• 英文别名: (3R)-3-(3,4-dichlorophenyl)-5-methoxy-5-oxopentanoic acid
• 化学式: C₁₂H₁₂Cl₂O₄
• 分子量: 291.131
• InChiKey: SNZJRKQCFHMMAC-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (R)-3-(3,4-dichlorophenyl)-glutaric acid monomethyl ester 在 disodium hydrogenphosphate 、 (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate 、 Selectfluor 作用下， 以 水 、 乙腈 为溶剂， 反应 12.0h， 以73.9 mg的产率得到methyl (R)-3-(3,4-dichlorophenyl)-4-fluorobutanoate
  参考文献：
  名称：

  Synthesis of Chiral Fluorides by Sequential Organocatalyzed Desymmetrization of Glutaric Anhydrides and Photoredox-Catalyzed Decarboxylic Fluorination

  摘要：

  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。

  DOI：

  10.1055/s-0040-1707295
• 作为产物：
  描述：

  3-(3,4-二氯苯基)戊二酸 在 Novozym 435 、 乙酰氯 作用下， 以 异丙醚 为溶剂， 反应 123.0h， 生成 (R)-3-(3,4-dichlorophenyl)-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

• CINCHONA-BASED BIFUNCTIONAL ORGANOCATALYSTS AND METHOD FOR PREPARING CHIRAL HEMIESTERS USING THE SAME
  申请人：SONG Choong Eui

  公开号：US20110213151A1

  公开（公告）日：2011-09-01

  The present invention relates to cinchona-based bifunctional organocatalysts and methods for preparing chiral hemiesters using the same. More specifically, the present invention relates to methods for preparing chiral hemiesters from prochiral or meso cyclic acid anhydrides via desymmetrization, using bifunctional cinchona alkaloid catalysts comprising sulfonamide functional groups.

  本发明涉及基于金鸡纳碱的双功能有机催化剂以及利用其制备手性半酯的方法。更具体地，本发明涉及利用含有磺酰胺功能团的双功能金鸡纳碱生催化剂，通过非对称化从原消旋或中性环酸酐制备手性半酯的方法。
• Enantioselective Alcoholysis of meso-Glutaric Anhydrides Catalyzed by Cinchona-Based Sulfonamide Catalysts
  作者：Sang Eun Park、Eun Hye Nam、Hyeong Bin Jang、Joong Suk Oh、Surajit Some、Yong Seop Lee、Choong Eui Song

  DOI：10.1002/adsc.201000289

  日期：2010.9.10

  The bifunctional Cinchona‐based sulfonamide catalysts showed the highest levels of enantioselectivity reported to date in the alcoholytic desymmetrization of meso‐glutaric anhydrides. Density functional theory (DFT) computational studies provide detailed insight into the observed sense of enantioselectivity. Moreover, detailed experimental studies and single crystal X‐ray analysis confirmed that these

  双功能金鸡纳为基础的磺胺催化剂表现出的对映选择性的最高水平的alcoholytic desymmetrization报告的日期观戊二酸酐。密度泛函理论（DFT）计算研究为观察到的对映选择性提供了详细的见识。此外，详细的实验研究和单晶X射线分析证实，这些双功能有机催化剂3在溶液和固态均不会形成H键结合的自聚集体。这种方法的合成效用还在合成重要的γ-氨基酸（例如（S）-普瑞巴林）中得到了证明。对映体纯（S的许多不对称合成）-迄今为止报道的普瑞巴林，我们的合成需要最少的步骤和最简单的步骤。
• US8580964B2
  申请人：——

  公开号：US8580964B2

  公开（公告）日：2013-11-12
• 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.
• 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。