1-(toluene-4-sulfonyl)-1-aza-spiro[2.4]heptane | 548461-35-4

• 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: 1-(toluene-4-sulfonyl)-1-aza-spiro[2.4]heptane
• 英文别名: 2-cyclopentyl-1-tosylaziridine；1-(4-Methylphenyl)sulfonyl-1-azaspiro[2.4]heptane
• CAS: 548461-35-4
• 化学式: C₁₃H₁₇NO₂S
• 分子量: 251.349
• InChiKey: KIBPXMMQGWATRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(toluene-4-sulfonyl)-1-aza-spiro[2.4]heptane 在 β-环糊精 叠氮基三甲基硅烷 作用下， 以 水 、 丙酮 为溶剂， 反应 24.0h， 以72%的产率得到1N-(1-azidomethylpentyl)-4-methyl-1-benzenesulfonamide
  参考文献：
  名称：

  β-环糊精在水中用亲核试剂高效仿生裂解氮丙啶

  摘要：

  β-环糊精首次在室温下在水中催化氮丙啶与芳香胺和叠氮化物等亲核试剂的轻松开环，分别以良好的产率得到二胺和叠氮胺。

  DOI：

  10.1246/cl.2001.246
• 作为产物：
  描述：

  (1-氨基环戊基)甲基氢硫酸盐 、 对甲苯磺酰氯 在 sodium hydroxide 、 三乙胺 作用下， 以 水 、 甲苯 为溶剂， 反应 30.0h， 以65%的产率得到1-(toluene-4-sulfonyl)-1-aza-spiro[2.4]heptane
  参考文献：
  名称：

  Observations on the Modified Wenker Synthesis of Aziridines and the Development of a Biphasic System

  摘要：

  A cheap and reliable process for the modified Wenker cyclization to afford aziridines has been achieved using biphasic conditions for a range of amino alcohol starting materials. A 100 mmol "one-pot" process has also been devised, and the enantiopurity of the starting amino alcohol is retained in the aziridine product.

  DOI：

  10.1021/jo302615g

文献信息

• Copper Catalyzed Synthesis of Thiomorpholine Derivatives: A New Entry of Multicomponent Reaction Between Terminal Alkynes, Isothiocyanates, and Aziridines
  作者：Alireza Samzadeh-Kermani

  DOI：10.1002/jhet.3418

  日期：2019.2

  Copper acetylide was reacted with isothiocyanate and aziridines to form 1,4‐thiomorpholine derivatives. Reaction outcome depends highly on the reaction conditions and the particular solvent employed. Optimum conditions are developed using copper iodide in hexafluoro‐2‐isopropanol at 60°C. Both the alkyl‐substituted and aryl‐substituted aziridines and terminal alkynes were studied.

  乙炔铜与异硫氰酸酯和氮丙啶反应形成1,4-硫吗啉衍生物。反应结果在很大程度上取决于反应条件和所用的特定溶剂。在60°C的六氟-2-异丙醇中使用碘化亚铜开发了最佳条件。研究了烷基取代的和芳基取代的氮丙啶和末端炔烃。
• ANTIFUNGAL AGENTS
  申请人：Greenlee Mark L

  公开号：US20110224228A1

  公开（公告）日：2011-09-15

  Novel derivatives of enfumafungin are disclosed herein, along with' their pharmaceutically acceptable salts, hydrates and prodrugs. Also disclosed are compositions comprising such compounds, methods of preparing such compounds and method of using such compounds as antifungal agents and/or inhibitors of (1,3)-β-D-glucan synthase. The disclosed compounds, their pharmaceutically acceptable salts, hydrates and prodrugs, as well as compositions comprising such compounds, salts, hydrates and prodrugs, are useful for treating and/or preventing fungal infections and associated diseases and conditions.

  本文披露了恩福马富金的新衍生物，以及它们的药物可接受的盐、水合物和前药。还披露了包含这些化合物的组合物，制备这些化合物的方法以及将这些化合物用作抗真菌剂和/或(1,3)-β-D-葡聚糖合酶的抑制剂的方法。所披露的化合物、它们的药物可接受的盐、水合物和前药，以及包含这些化合物、盐、水合物和前药的组合物，对于治疗和/或预防真菌感染和相关疾病和病况是有用的。
• Development of a [3+3] Cycloaddition Strategy toward Functionalized Piperidines
  作者：Simon J. Hedley、Wesley J. Moran、David A. Price、Joseph P. A. Harrity

  DOI：10.1021/jo030002c

  日期：2003.5.1

  This paper describes a novel route to functionalized piperidines via a formal [3+3] cycloaddition reaction of activated aziridines and palladium-trimethylenemethane (Pd-TMM) complexes. The cycloaddition reaction generally proceeds enantiospecifically with ring opening at the least hindered site of the aziridine. Therefore, readily available enantiomerically pure 2-substituted aziridines can be utilized to prepare enantiomerically pure 2-substituted piperidines in good to excellent yield. The N-substituent on the aziridine proved to be crucial to the success of this reaction with only 4-toluenesulfonyl (Ts) and 4-methoxybenzenesulfonyl (PMBS) aziridines permitting smooth cycloaddition to take place. Additionally, spirocyclic aziridines have been found to participate in the [3+3] cycloaddition reaction, whereas 2,3-disubstituted aziridines can be applied to provide fused bicyclic piperidines, albeit in low yield.
• US8722727B2
  申请人：——

  公开号：US8722727B2

  公开（公告）日：2014-05-13
• An Efficient Biomimetic Cleavage of Aziridines with Nucleophiles Catalyzed by β-Cyclodextrin in Water
  作者：M. Arjun Reddy、L. Rajender Reddy、N. Bhanumathi、K. Rama Rao

  DOI：10.1246/cl.2001.246

  日期：2001.3

  β-Cyclodextrin catalyzed for the first time a facile ring opening of aziridines with nucleophiles such as aromatic amines and azides in water at room temperature to afford diamines and azidoamines respectively in good yields.

  β-环糊精首次在室温下在水中催化氮丙啶与芳香胺和叠氮化物等亲核试剂的轻松开环，分别以良好的产率得到二胺和叠氮胺。