(2R)-1-苄基-2-甲基氮杂环丁烷-2-羧酸甲酯 | 1179839-12-3

• 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
• 中文名称: (2R)-1-苄基-2-甲基氮杂环丁烷-2-羧酸甲酯
• 英文名称: (R)-1-benzyl-2-methyl-azetidine-2-carboxylic acid methyl ester
• 英文别名: (R)-(+)-methyl 1-benzyl-2-methylazetidine-2-carboxylate；methyl (2R)-1-benzyl-2-methylazetidine-2-carboxylate
• CAS: 1179839-12-3
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: QGWMCHHETIEPNT-CYBMUJFWSA-N

物化性质

• 沸点：
  278.3±33.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-1-苄基-2-甲基氮杂环丁烷-2-羧酸甲酯 在 盐酸 、 20 % Pd(OH)2/C 、 氢气 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 反应 16.0h， 生成 (2R)-1-((S)-2-tert-butoxycarbonylamino-propionyl)-2-methylazetidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Practical preparation of enantiopure 2-methyl-azetidine-2-carboxylic acid; a γ-turn promoter

  摘要：

  A robust and practical synthesis of each enantiomer of 2-methyl-azetidine-2-carboxylic acid, based on the use of (S)-phenylglycinol as resolving agent, is described. This synthesis affords practical quantities of this quaternary amino acid suitably N- and C-protected for use in further peptide coupling. Synthetic highlights include the formation of the azetidine ring by intramolecular alkylation and the facile separation of the diastereoisomeric amides derived from phenylglycinol. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.006
• 作为产物：
  描述：

  Tert-butyl 1-benzyl-2-methylazetidine-2-carboxylate 在 硫酸 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (2R)-1-苄基-2-甲基氮杂环丁烷-2-羧酸甲酯
  参考文献：
  名称：

  Practical preparation of enantiopure 2-methyl-azetidine-2-carboxylic acid; a γ-turn promoter

  摘要：

  A robust and practical synthesis of each enantiomer of 2-methyl-azetidine-2-carboxylic acid, based on the use of (S)-phenylglycinol as resolving agent, is described. This synthesis affords practical quantities of this quaternary amino acid suitably N- and C-protected for use in further peptide coupling. Synthetic highlights include the formation of the azetidine ring by intramolecular alkylation and the facile separation of the diastereoisomeric amides derived from phenylglycinol. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.05.006

文献信息

• [EN] AZETIDINE DERIVATIVES USEFUL FOR THE TREATMENT OF METABOLIC AND INFLAMMATORY DISEASES<br/>[FR] DÉRIVÉS D'AZÉTIDINE UTILES POUR LE TRAITEMENT DE MALADIES MÉTABOLIQUES ET INFLAMMATOIRES
  申请人：GALAPAGOS NV

  公开号：WO2012098033A1

  公开（公告）日：2012-07-26

  Compounds are disclosed that have a formula represented by the following: These compounds may be prepared as a pharmaceutical composition, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example inflammatory conditions, infectious diseases, autoimmune diseases, diseases involving impairment of immune cell functions, cardiometabolic diseases, and/or proliferative diseases.

  披露了具有以下表示的公式的化合物：这些化合物可以制备为药物组合物，并可用于预防和治疗包括人类在内的哺乳动物的各种疾病，例如炎症性疾病、传染病、自身免疫疾病、涉及免疫细胞功能受损的疾病、心脏代谢疾病和/或增殖性疾病，举例不限。
• NOVEL COMPOUNDS USEFUL FOR THE TREATMENT OF METABOLIC AND INFLAMMATORY DISEASES
  申请人：Sanière Laurent Raymond Maurice

  公开号：US20130303515A1

  公开（公告）日：2013-11-14

  Compounds are disclosed that have a formula represented by the following: These compounds may be prepared as a pharmaceutical composition, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example inflammatory conditions, infectious diseases, autoimmune diseases, diseases involving impairment of immune cell functions, cardiometabolic diseases, and/or proliferative diseases.

  公开了具有以下式子表示的化合物：这些化合物可以制备成药物组合物，并可用于哺乳动物，包括人类的预防和治疗，例如炎症性疾病、传染病、自身免疫疾病、涉及免疫细胞功能受损的疾病、心脏代谢疾病和/或增殖性疾病等。
• Compounds useful for the treatment of metabolic and inflammatory diseases
  申请人：Sanière Laurent Raymond Maurice

  公开号：US08759334B2

  公开（公告）日：2014-06-24

  Compounds are disclosed that have a formula represented by the following: These compounds may be prepared as a pharmaceutical composition, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example inflammatory conditions, infectious diseases, autoimmune diseases, diseases involving impairment of immune cell functions, cardiometabolic diseases, and/or proliferative diseases.

  揭示了具有以下公式表示的化合物：这些化合物可以制备为药物组合物，并可用于哺乳动物，包括人类的预防和治疗各种疾病，例如炎症性疾病、传染病、自身免疫疾病、涉及免疫细胞功能受损的疾病、心血管代谢疾病和/或增殖性疾病，举例而言。
• Highly Efficient and Enantioselective Biotransformations of Racemic Azetidine-2-carbonitriles and Their Synthetic Applications
  作者：Dong-Hui Leng、De-Xiang Wang、Jie Pan、Zhi-Tang Huang、Mei-Xiang Wang

  DOI：10.1021/jo9011656

  日期：2009.8.21

  Catalyzed by the Rhodococcus erythropolis AJ270 whole cell catalyst in neutral aqueous buffer at 30 degrees C, a number of racemic 1-benzylazetidine-2-carbonitriles, trans-1-benzyl-4-methylazetidine-2-carbonitrile. and 1-benzyl-2-methylazetidine-2-carbonitrile and their amide substrates underwent efficient and enantioselective biotransformations to afford the corresponding azetidine-2-carboxylic acids and their amide derivatives in excellent yields with cc up to >99.5%. The overall excellent, act enantioselectivity of the biocatalytic reactions stemmed from a combined effect of a very active but virtually nonenantioselective nitrite hydratase and a high R-enantioselective amidase involved in microbial whole cells. The synthetic applications have been demonstrated by the nucleophilic ring-opening reactions of azetidiniums of the resulting chiral azetidine-2-carbox amide derivatives for the preparation of alpha,gamma-diamino, alpha-phenoxy-gamma-amino, and alpha-cyano-gamma-amino carboxamides. The intramolecular Cul-catalyzed cross-coupling reaction for the synthesis of azetidine-fused 1,4-benzodiazepin-2-one derivative was also presented.
• AZETIDINE DERIVATIVES USEFUL FOR THE TREATMENT OF METABOLIC AND INFLAMMATORY DISEASES
  申请人：Galapagos NV

  公开号：EP2665704A1

  公开（公告）日：2013-11-27