methyl N-benzoyl-5-(2,4,6-trimethylphenyl)-L-prolinate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl N-benzoyl-5-(2,4,6-trimethylphenyl)-L-prolinate
• 英文别名: methyl (2S)-1-benzoyl-5-(2,4,6-trimethylphenyl)pyrrolidine-2-carboxylate
• 化学式: C₂₂H₂₅NO₃
• 分子量: 351.445
• InChiKey: ULSBBTLXWYPQIA-GGYWPGCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl N-benzoyl-5-(2,4,6-trimethylphenyl)-L-prolinate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以58%的产率得到trans-N-benzoyl-5-(2,4,6-trimethylphenyl)-L-proline
  参考文献：
  名称：

  Diastereoselective arylation of l-proline derivatives at the 5-position

  摘要：

  Diastereoselective introduction of nucleophiles into L-proline derivatives at the 5-position was achieved with suitable selection of N-protecting group. N-Methoxycarbonylated or benzyloxycarbonylated L-proline derivatives reacted with arene to give cis-arylated products. On the other hand, N-benzoylated L-proline derivative preferentially gave trans-arylated product, which could be easily transformed into optically active C-2-symmetrical pyrrolidine derivative. Such derivative 5 worked well as an organic activator in the asymmetric reduction of aromatic imines by Cl3SiH. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.004
• 作为产物：
  描述：

  1-Benzoyl-2-methoxy-5-(methoxycarbonyl)pyrrolidine 、 均三甲苯 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到methyl N-benzoyl-5-(2,4,6-trimethylphenyl)-L-prolinate
  参考文献：
  名称：

  Diastereoselective arylation of l-proline derivatives at the 5-position

  摘要：

  Diastereoselective introduction of nucleophiles into L-proline derivatives at the 5-position was achieved with suitable selection of N-protecting group. N-Methoxycarbonylated or benzyloxycarbonylated L-proline derivatives reacted with arene to give cis-arylated products. On the other hand, N-benzoylated L-proline derivative preferentially gave trans-arylated product, which could be easily transformed into optically active C-2-symmetrical pyrrolidine derivative. Such derivative 5 worked well as an organic activator in the asymmetric reduction of aromatic imines by Cl3SiH. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.004

文献信息

• [EN] COMPOUNDS, PHARMACEUTICAL COMPOSITION AND METHODS FOR USE IN TREATING INFLAMMATORY DISEASES<br/>[FR] COMPOSÉS, COMPOSITION PHARMACEUTIQUE ET MÉTHODES À UTILISER DANS LE TRAITEMENT DE MALADIES INFLAMMATOIRES
  申请人：EUROSCREEN SA

  公开号：WO2015078949A1

  公开（公告）日：2015-06-04

  The present invention is directed to compounds of formula (I), useful in treating and/or preventing inflammatory diseases.

  本发明涉及一种化合物，其化学式为(I)，用于治疗和/或预防炎症性疾病。
• [EN] PYRROLIDINE OR THIAZOLIDINE CARBOXYLIC ACID DERIVATIVES, PHARMACEUTICAL COMPOSITION AND METHODS FOR USE IN TREATING METABOLIC DISORDERSAS AS AGONISTS OF G- PROTEIN COUPLED RECEPTOR 43 (GPR43)<br/>[FR] COMPOSÉS, COMPOSITION PHARMACEUTIQUE ET MÉTHODES POUR APPLICATION AU TRAITEMENT DE TROUBLES MÉTABOLIQUES
  申请人：EUROSCREEN SA

  公开号：WO2011073376A1

  公开（公告）日：2011-06-23

  The present invention is directed to novel compounds of formula (I) and their use in treating and/or preventing metabolic diseases.

  本发明涉及具有式（I）的新化合物，以及它们在治疗和/或预防代谢性疾病中的用途。
• PYRROLIDINE OR THIAZOLIDINE CARBOXYLIC ACID DERIVATIVES, PHARMACEUTICAL COMPOSITION AND METHODS FOR USE IN TREATING METABOLIC DISORDERS AS AGONISTS OF G-PROTEIN COUPLED RECEPTOR 43 (GPR43)
  申请人：Hoveyda Hamid R.

  公开号：US20130023539A1

  公开（公告）日：2013-01-24

  The present invention is directed to novel compounds of formula (I) and their use in treating and/or preventing metabolic diseases.

  本发明涉及式（I）的新化合物及其在治疗和/或预防代谢性疾病方面的应用。
• Substituted pyrrolidines as G-protein coupled receptor 43 agonists
  申请人：Ogeda SA

  公开号：US10017468B2

  公开（公告）日：2018-07-10

  The present invention is directed to a process for the preparation of aryl-pyrrolidine carboxylic acid derivative compounds which are useful in treating metabolic diseases, said process consisting of coupling an aryl-pyrrolidine compound with an aryl carboxylic acid compound followed by alkaline or acidic treatment, hydrogenolysis or treatment with a fluoride of the ester intermediate to afford novel aryl-pyrrolidine carboxylic acid derivative compounds.

  本发明涉及一种用于制备治疗代谢性疾病的芳基吡咯烷羧酸衍生物化合物的工艺，所述工艺包括将芳基吡咯烷化合物与芳基羧酸化合物偶联，然后对酯类中间体进行碱性或酸性处理、氢解或用氟化物处理，以得到新型芳基吡咯烷羧酸衍生物化合物。
• PYRROLIDINE OR THIAZOLIDINE CARBOXYLIC ACID DERIVATIVES, PHARMACEUTICAL COMPOSITION AND METHODS FOR USE IN TREATING METABOLIC DISORDERSAS AS AGONISTS OF G- PROTEIN COUPLED RECEPTOR 43 (GPR43)
  申请人：Euroscreen S.A.

  公开号：EP2513053A1

  公开（公告）日：2012-10-24