benzyl 3-(4-chlorophenyl)-2,5-dihydro-1H-pyrrole-1-carboxylate | 877614-85-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 3-(4-chlorophenyl)-2,5-dihydro-1H-pyrrole-1-carboxylate
• 英文别名: Benzyl 3-(4-chlorophenyl)-2,5-dihydropyrrole-1-carboxylate
• CAS: 877614-85-2
• 化学式: C₁₈H₁₆ClNO₂
• 分子量: 313.784
• InChiKey: BXWIVAKFYCSJGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzyl 3-(4-chlorophenyl)-2,5-dihydro-1H-pyrrole-1-carboxylate 在 palladium on activated charcoal ruthenium trichloride 、 sodium periodate 、 氢气 作用下， 以 甲醇 、 四氯化碳 、 乙腈 为溶剂， 反应 16.0h， 生成 (±)-tert-butyl (R)-4-(4-chlorophenyl)-2-oxopyrrolidine-1-carboxylate
  参考文献：
  名称：

  New synthesis of 3-arylpyrrolines

  摘要：

  We present an easy and straightforward synthesis of 3-arylpyrrolines 4a-g by repeated treatment of 4-aryl-1,2,5,6-tetrahydropyridines 2a-g with in-chloroperoxybenzoic acid (MCPBA) and boron trifluoride etherate (BF3-OEt2). The transformation proceeds via epoxidation, ring contraction, Baeyer-Villiger oxidation and elimination reaction and affords 3-arylpyrrolines 4a-g with 61-70% yield. This facile strategy was also used to synthesize racemic baclofen (6). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.12.008
• 作为产物：
  描述：

  benzyl 4-(4-chlorophenyl)-3,6-dihydropyridine-1(2H)-carboxylate 在 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 生成 benzyl 3-(4-chlorophenyl)-2,5-dihydro-1H-pyrrole-1-carboxylate
  参考文献：
  名称：

  New synthesis of 3-arylpyrrolines

  摘要：

  We present an easy and straightforward synthesis of 3-arylpyrrolines 4a-g by repeated treatment of 4-aryl-1,2,5,6-tetrahydropyridines 2a-g with in-chloroperoxybenzoic acid (MCPBA) and boron trifluoride etherate (BF3-OEt2). The transformation proceeds via epoxidation, ring contraction, Baeyer-Villiger oxidation and elimination reaction and affords 3-arylpyrrolines 4a-g with 61-70% yield. This facile strategy was also used to synthesize racemic baclofen (6). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.12.008

文献信息

• Catalytic Friedel‐Crafts Reactions on Saturated Heterocycles and Small Rings for sp ³ ‐sp ² Coupling of Medicinally Relevant Fragments
  作者：Rosemary A. Croft、Maryne A. J. Dubois、Alexander J. Boddy、Camille Denis、Anna Lazaridou、Anne Sophie Voisin‐Chiret、Ronan Bureau、Chulho Choi、James J. Mousseau、James A. Bull

  DOI：10.1002/ejoc.201900498

  日期：2019.9

  A systematic comparison of Lewis acid catalysts [Ca(II), Li(I) and Fe(III)] is presented for catalytic Friedel–Crafts reactions using alcohols on 4‐, 5‐, and 6‐membered oxygen and nitrogen heterocycles and cyclobutanes, forming gem‐diaryl quaternary centers.

  路易斯酸催化剂[Ca（II），Li（I）和Fe（III）]的系统比较被提出用于使用醇在4、5和6元氧和氮杂环和环丁烷上进行的催化Friedel-Crafts反应，形成宝石-二芳基四元中心。
• [EN] SUBSTITUTED CYCLIC MODULATORS OF PROTEIN PHOSPHATASE 2A (PP2A) AND METHODS USING SAME<br/>[FR] MODULATEURS CYCLIQUES SUBSTITUÉS DE PROTÉINE PHOSPHATASE 2A (PP2A) ET LEURS PROCÉDÉS D'UTILISATION
  申请人：RAPPTA THERAPEUTICS OY

  公开号：WO2022167867A1

  公开（公告）日：2022-08-11

  The present disclosure relates in part to chemical modulators of protein phosphatase 2A (PP2A). The compounds of the present disclosure are useful in treating, preventing, and/or ameliorating cancer, diabetes, autoimmune disease, solid organ transplant rejection, graft vs host disease, chronic obstructive pulmonary disease (COPD), non-alcoholic fatty liver disease, abdominal aortic aneurysm, chronic liver disease, heart failure, neurodegenerative disease, and cardiac hypertrophy.

  本公开涉及部分蛋白磷酸酶2A（PP2A）的化学调节剂。本公开的化合物可用于治疗、预防和/或改善癌症、糖尿病、自身免疫性疾病、固体器官移植排斥、移植物抗宿主病、慢性阻塞性肺疾病（COPD）、非酒精性脂肪性肝病、腹主动脉瘤、慢性肝病、心力衰竭、神经退行性疾病和心肌肥厚。
• New synthesis of 3-arylpyrrolines
  作者：Meng-Yang Chang、Chun-Li Pai、Yung-Hua Kung

  DOI：10.1016/j.tetlet.2005.12.008

  日期：2006.2

  We present an easy and straightforward synthesis of 3-arylpyrrolines 4a-g by repeated treatment of 4-aryl-1,2,5,6-tetrahydropyridines 2a-g with in-chloroperoxybenzoic acid (MCPBA) and boron trifluoride etherate (BF3-OEt2). The transformation proceeds via epoxidation, ring contraction, Baeyer-Villiger oxidation and elimination reaction and affords 3-arylpyrrolines 4a-g with 61-70% yield. This facile strategy was also used to synthesize racemic baclofen (6). (c) 2005 Elsevier Ltd. All rights reserved.