2-甲基-1-[(4-甲基苯基)磺酰基]吖丁啶 | 13595-47-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-甲基-1-[(4-甲基苯基)磺酰基]吖丁啶
• 英文名称: 2-Methyl-N-p-tosyl-azetidid
• 英文别名: N-Tosyl-2-methylazetidin；2-methyl-1-(toluene-4-sulfonyl)-azetidine；Azetidine, 2-methyl-1-(p-tolylsulfonyl)-；2-methyl-1-(4-methylphenyl)sulfonylazetidine
• CAS: 13595-47-6
• 化学式: C₁₁H₁₅NO₂S
• 分子量: 225.312
• InChiKey: LAQQJOLVFQMWPB-UHFFFAOYSA-N

物化性质

• 沸点：
  342.2±35.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-甲基-1-[(4-甲基苯基)磺酰基]吖丁啶 在 sodium 作用下， 以 戊醇 为溶剂， 生成 (+/-)-2-甲基氮杂丁烷
  参考文献：
  名称：

  Novel Acetylcholine and Carbamoylcholine Analogues: Development of a Functionally Selective α₄β₂ Nicotinic Acetylcholine Receptor Agonist

  摘要：

  A series of carbamoylcholine and acetylcholine analogues were synthesized and characterized pharmacologically at neuronal nicotinic acetylcholine receptors (nAChRs). Several of the compounds displayed low nanomolar binding affinities to the alpha(4)beta(2) nAChR and pronounced selectivity for this subtype over alpha(3)beta(4), alpha(4)beta(4), and alpha(7) nAChRs. The high nAChR activity of carbamoylcholine analogue 5d was found to reside in its R-enantiomer, a characteristic most likely true for all other compounds in the series. Interestingly, the pronounced alpha(4)beta(2) selectivities exhibited by some of the compounds in the binding assays translated into functional selectivity. Compound 5a was a fairly potent partial alpha(4)beta(2) nAChR agonist with negligible activities at the alpha(3)beta(4) and alpha(7) subtypes, thus being one of the few truly functionally selective alpha(4)beta(2) nAChR agonists published to date. Ligand-protein docking experiments using homology models of the amino-terminal domains of alpha(4)beta(2) and alpha(3)beta(4) nAChRs identified residues Val 111(beta(2))/Ile 113(beta(4)), Phe 119(beta(2))/Gln 121(beta(4)), and Thr155(alpha(4))/Ser 150(alpha(3)) as possible key determinants of the alpha(4)beta(2)/alpha(3)beta(4)-selectivity displayed by the analogues. 4

  DOI：

  10.1021/jm701625v
• 作为产物：
  描述：

  4-(p-Toluolsulfonamido)-2-butyl-p-toluolsulfonat 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 生成 2-甲基-1-[(4-甲基苯基)磺酰基]吖丁啶
  参考文献：
  名称：

  Novel Acetylcholine and Carbamoylcholine Analogues: Development of a Functionally Selective α₄β₂ Nicotinic Acetylcholine Receptor Agonist

  摘要：

  A series of carbamoylcholine and acetylcholine analogues were synthesized and characterized pharmacologically at neuronal nicotinic acetylcholine receptors (nAChRs). Several of the compounds displayed low nanomolar binding affinities to the alpha(4)beta(2) nAChR and pronounced selectivity for this subtype over alpha(3)beta(4), alpha(4)beta(4), and alpha(7) nAChRs. The high nAChR activity of carbamoylcholine analogue 5d was found to reside in its R-enantiomer, a characteristic most likely true for all other compounds in the series. Interestingly, the pronounced alpha(4)beta(2) selectivities exhibited by some of the compounds in the binding assays translated into functional selectivity. Compound 5a was a fairly potent partial alpha(4)beta(2) nAChR agonist with negligible activities at the alpha(3)beta(4) and alpha(7) subtypes, thus being one of the few truly functionally selective alpha(4)beta(2) nAChR agonists published to date. Ligand-protein docking experiments using homology models of the amino-terminal domains of alpha(4)beta(2) and alpha(3)beta(4) nAChRs identified residues Val 111(beta(2))/Ile 113(beta(4)), Phe 119(beta(2))/Gln 121(beta(4)), and Thr155(alpha(4))/Ser 150(alpha(3)) as possible key determinants of the alpha(4)beta(2)/alpha(3)beta(4)-selectivity displayed by the analogues. 4

  DOI：

  10.1021/jm701625v

文献信息

• A Facile Synthesis of 1-Arenesulfonylazetidines through Reaction of 1-Arenesulfonylaziridines with Dimethylsulfoxonium Methylide Generated under Microwave Irradiation
  作者：Sarika Malik、Upender Nadir

  DOI：10.1055/s-2007-1000838

  日期：2008.1

  A simple, efficient and general method has been developed for the synthesis of 1 -arenesulfonylazetidines through a one-pot reaction of 1-arenesulfonylaziridines with dimethylsulfoxonium methylide, generated under microwave irradiation, using alumi- R 2 na as solid support.

  已经开发了一种简单、有效和通用的方法来合成 1-芳烃磺酰基氮杂环丁烷，通过 1-芳烃磺酰基氮杂环丁烷与二甲基亚砜的一锅反应，在微波辐射下产生，使用铝-R 2 na 作为固体载体。
• Electrocatalytic Access to Azetidines via Intramolecular Allylic Hydroamination: Scrutinizing Key Oxidation Steps through Electrochemical Kinetic Analysis
  作者：Steve H. Park、Geunsu Bae、Ahhyeon Choi、Suyeon Shin、Kwangmin Shin、Chang Hyuck Choi、Hyunwoo Kim

  DOI：10.1021/jacs.3c03172

  日期：2023.7.19

  regioselective generation of key carbocationic intermediates, which could directly undergo intramolecular C–N bond formation. The mechanistic investigations including electrochemical kinetic analysis suggest that either the catalyst regeneration by nucleophilic cyclization or the second electrochemical oxidation to access the carbocationic intermediate is involved in the rate-determining step (RDS) of our electrochemical

  氮杂环丁烷是生物活性分子、药物化学和过渡金属配体设计中的重要结构支架。然而，最先进的方法不能应用于烯丙胺衍生物的分子内加氢胺化，尽管它们具有作为氮杂环丁烷最普遍的合成前体之一的潜在潜力。在此，我们首次报道了一种烯丙基磺酰胺分子内氢胺化的电催化方法，以获取氮杂环丁烷。钴催化和电的结合使得关键碳阳离子中间体的区域选择性生成成为可能，该中间体可以直接形成分子内C-N键。包括电化学动力学分析在内的机理研究表明，通过亲核环化进行的催化剂再生或获得碳阳离子中间体的第二次电化学氧化都参与了我们电化学方案的速率决定步骤（RDS），并强调了电化学提供理想反应的能力。是指介导催化剂氧化。
• Nadir, Upender K.; Sharma, Ms. Raman L.; Koul, Veerinder K., Journal of the Chemical Society. Perkin transactions I, 1991, # 8, p. 2015 - 2020
  作者：Nadir, Upender K.、Sharma, Ms. Raman L.、Koul, Veerinder K.

  DOI：——

  日期：——
• Novel Acetylcholine and Carbamoylcholine Analogues: Development of a Functionally Selective α₄β₂ Nicotinic Acetylcholine Receptor Agonist
  作者：Camilla P. Hansen、Anders A. Jensen、Jeppe K. Christensen、Thomas Balle、Tommy Liljefors、Bente Frølund

  DOI：10.1021/jm701625v

  日期：2008.12.11

  A series of carbamoylcholine and acetylcholine analogues were synthesized and characterized pharmacologically at neuronal nicotinic acetylcholine receptors (nAChRs). Several of the compounds displayed low nanomolar binding affinities to the alpha(4)beta(2) nAChR and pronounced selectivity for this subtype over alpha(3)beta(4), alpha(4)beta(4), and alpha(7) nAChRs. The high nAChR activity of carbamoylcholine analogue 5d was found to reside in its R-enantiomer, a characteristic most likely true for all other compounds in the series. Interestingly, the pronounced alpha(4)beta(2) selectivities exhibited by some of the compounds in the binding assays translated into functional selectivity. Compound 5a was a fairly potent partial alpha(4)beta(2) nAChR agonist with negligible activities at the alpha(3)beta(4) and alpha(7) subtypes, thus being one of the few truly functionally selective alpha(4)beta(2) nAChR agonists published to date. Ligand-protein docking experiments using homology models of the amino-terminal domains of alpha(4)beta(2) and alpha(3)beta(4) nAChRs identified residues Val 111(beta(2))/Ile 113(beta(4)), Phe 119(beta(2))/Gln 121(beta(4)), and Thr155(alpha(4))/Ser 150(alpha(3)) as possible key determinants of the alpha(4)beta(2)/alpha(3)beta(4)-selectivity displayed by the analogues. 4