3-methyl-1-tosylazetidine | 35197-04-7

• 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: 3-methyl-1-tosylazetidine
• 英文别名: 3-Methyl-1-(4-methylphenyl)sulfonylazetidine
• CAS: 35197-04-7
• 化学式: C₁₁H₁₅NO₂S
• 分子量: 225.312
• InChiKey: VPKICTKHRFCHPA-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

反应信息

• 作为反应物：
  描述：

  3-methyl-1-tosylazetidine 在 盐酸 、 水 、 sodium 作用下， 以 戊醇 、 水 为溶剂， 以90%的产率得到3-甲基氮杂环丁烷盐酸盐
  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：

  2-methyl-3-(4-methylphenylsulfonamido)propyl 4-methylbenzenesulfonate 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 以88%的产率得到3-methyl-1-tosylazetidine
  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

• Cobalt-Catalyzed Decarboxylative Methylation and Ethylation of Aliphatic N-(Acyloxy)phthalimides with Organoaluminum Reagents
  作者：Rui Shang、Yao Fu、Ze-Zhong Wang、Guang-Zu Wang、Bin Zhao

  DOI：10.1055/s-0040-1707946

  日期：2020.7

  A cobalt-catalyzed decarboxylative methylation of aliphatic redox-active esters [N-(acyloxy)phthalimides; RAEs] with trimethylaluminum under mild conditions was developed, providing a method for transforming a carboxylate group into a methyl group without redox fluctuation. Primary and secondary RAEs were both amenable substrates, whereas a tertiary RAE delivered an elimination product. Triethylaluminum

  脂肪族氧化还原活性酯 [N-（酰氧基）邻苯二甲酰亚胺；RAEs] 与三甲基铝在温和条件下的开发，提供了一种将羧酸盐基团转化为甲基基团而没有氧化还原波动的方法。一级和二级 RAE 都是适合的底物，而三级 RAE 提供消除产物。三乙基铝也用于提供脱羧乙基化产物。
• Direct Alkylation of 1-Azabicyclo[1.1.0]butanes
  作者：Ryan Gianatassio、Dora Kadish

  DOI：10.1021/acs.orglett.9b00321

  日期：2019.4.5

  functionalized azetidines has been an ongoing challenge. Here, we report a general method to directly alkylate 1-azabicyclo[1.1.0]butane (ABB) with organometal reagents in the presence of Cu(OTf)2 to rapidly prepare bis-functionalized azetidines. This method allows for the preparation of azetidines bearing alkyl, allyl, vinyl, and benzyl groups. This catalyst system was extended to aziridines and spirocycles

  容易的功能化氮杂环丁烷的合成一直是一个持续的挑战。在这里，我们报告了一种在Cu（OTf）2存在下用有机金属试剂直接烷基化1-氮杂双环[1.1.0]丁烷（ABB）的一般方法，以快速制备双官能化氮杂环丁烷。该方法允许制备带有烷基，烯丙基，乙烯基和苄基的氮杂环丁烷。该催化剂体系扩展到氮丙啶和螺环。快速且高收率地制备了几种结构单元和类药物化合物。
• [EN] BET BROMODOMAIN INHIBITORS AND THERAPEUTIC METHODS USING THE SAME<br/>[FR] INHIBITEURS DE BROMODOMAINES BET ET MÉTHODES THÉRAPEUTIQUES LES UTILISANT
  申请人：UNIV MICHIGAN

  公开号：WO2014164596A1

  公开（公告）日：2014-10-09

  Inhibitors of BET bromodomains and compositions containing the same are disclosed. Methods of using the BET bromodomain inhibitors in the treatment of diseases and conditions wherein inhibition of BET bromodomain provides a benefit, like cancers, also are disclosed.

  本文披露了BET bromodomain抑制剂及含有它们的组合物。还披露了使用BET bromodomain抑制剂治疗疾病和状况的方法，其中BET bromodomain的抑制提供益处，如癌症等疾病。
• BET BROMODOMAIN INHIBITORS AND THERAPEUTIC METHODS USING THE SAME
  申请人：The Regents of The University of Michigan

  公开号：EP2970312B1

  公开（公告）日：2017-11-15
• US20140256706A1
  申请人：——

  公开号：US20140256706A1

  公开（公告）日：2014-09-11