1-(naphthalen-1-ylsulfonyl)-2-phenylaziridine | 1017610-01-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(naphthalen-1-ylsulfonyl)-2-phenylaziridine
• 英文别名: 1-Naphthalen-1-ylsulfonyl-2-phenylaziridine
• CAS: 1017610-01-3
• 化学式: C₁₈H₁₅NO₂S
• 分子量: 309.389
• InChiKey: ZPWNIWMRRLRKHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯乙烯 、 naphthalene-1-sulfonyl azide 在 copper acetylacetonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 1-(naphthalen-1-ylsulfonyl)-2-phenylaziridine
  参考文献：
  名称：

  利用螯合的2-吡啶基磺酰基部分在催化烯烃叠氮化中铜-类异戊二烯的形成和转移

  摘要：

  我们已经开发出一种有效的方案，用于使用5-甲基-2-吡啶磺酰胺或2-吡啶磺酰基叠氮化物作为类固醇源的铜催化烯烃叠氮化。2-吡啶基的存在显着促进了叠氮基化，表明该反应是由吡啶基配位的亚硝基化合物中间体的有利形成驱动的。使用这种螯合辅助策略，即使在没有外部配体的情况下，使用一系列芳基烯烃也可以获得合成可接受的氮丙啶收率。重要的是，不需要大量过量的烯烃。X射线晶体学，ESI-MS，哈米特图分析，动力学研究和计算工作都强烈支持观察到的叠氮化是由内部配位驱动的。

  DOI：

  10.1021/jo800134j

文献信息

• Copper−Nitrenoid Formation and Transfer in Catalytic Olefin Aziridination Utilizing Chelating 2-Pyridylsulfonyl Moieties
  作者：Hoon Han、Seong Byeong Park、Sang Kyu Kim、Sukbok Chang

  DOI：10.1021/jo800134j

  日期：2008.4.1

  developed an efficient protocol for copper-catalyzed olefin aziridination using 5-methyl-2-pyridinesulfonamide or 2-pyridinesulfonyl azide as the nitrenoid source. The presence of a 2-pyridyl group significantly facilitates aziridination, suggesting that the reaction is driven by the favorable formation of a pyridyl-coordinated nitrenoid intermediate. Using this chelation-assisted strategy, synthetically

  我们已经开发出一种有效的方案，用于使用5-甲基-2-吡啶磺酰胺或2-吡啶磺酰基叠氮化物作为类固醇源的铜催化烯烃叠氮化。2-吡啶基的存在显着促进了叠氮基化，表明该反应是由吡啶基配位的亚硝基化合物中间体的有利形成驱动的。使用这种螯合辅助策略，即使在没有外部配体的情况下，使用一系列芳基烯烃也可以获得合成可接受的氮丙啶收率。重要的是，不需要大量过量的烯烃。X射线晶体学，ESI-MS，哈米特图分析，动力学研究和计算工作都强烈支持观察到的叠氮化是由内部配位驱动的。
• Metal Porphyrin Catalyzed Olefin Aziridination with Sulfonyl Azides
  申请人：Zhang X. Peter

  公开号：US20110112288A1

  公开（公告）日：2011-05-12

  Cobalt(II) complex of P1 [Co(P1)], a new porphyrin that was designed on the basis of potential hydrogen bonding interactions in the metal-nitrene intermediate, is a highly active catalyst for olefin aziridination with azides. The [Co(P1)]-based system can be effectively employed for different combinations of aromatic olefins and arysulfonyl azides, synthesizing various sulfonylated aziridines in excellent yields. Besides its mild catalytic conditions, the Co-catalyzed aziridination process enjoys several attributes associated with the relatively low cost of cobalt and widely accessible arylsulfonyl azides. Furthermore, it generates stable dinitrogen as the only by-product.
• [EN] METAL PORPHYRIN CATALYZED OLEFIN AZIRIDINATION WITH SULFONYL AZIDES<br/>[FR] AZIRIDINATION D'OLÉFINES CATALYSÉE PAR UNE PORPHYRINE MÉTALLIQUE AVEC DES SULFONYLAZIDES
  申请人：UNIV SOUTH FLORIDA

  公开号：WO2009146032A2

  公开（公告）日：2009-12-03

  Cobalt(II) complex of P1 [Co(P1)], a new porphyrin that was designed on the basis of potential hydrogen bonding interactions in the metal-nitrene intermediate, is a highly active catalyst for olefin aziridination with azides. The [Co(P1)]- based system can be effectively employed for different combinations of aromatic olefins and arysulfonyl azides, synthesizing various sulfonylated aziridines in excellent yields. Besides its mild catalytic conditions, the Co-catalyzed aziridination process enjoys several attributes associated with the relatively low cost of cobalt and widely accessible arylsulfonyl azides. Furthermore, it generates stable dinitrogen as the only by-product.
• A Highly Effective Cobalt Catalyst for Olefin Aziridination with Azides: Hydrogen Bonding Guided Catalyst Design
  作者：Joshua V. Ruppel、Jess E. Jones、Chelsea A. Huff、Rajesh M. Kamble、Ying Chen、X. Peter Zhang

  DOI：10.1021/ol800588p

  日期：2008.5.1

  [Co(P1)], which was designed on the basis of potential hydrogen-bonding interactions in the metal-nitrene intermediate, is a highly active aziridination catalyst with azides. [Co(P1)] can effectively aziridinate various aromatic olefins with arylsulfonyl azides under mild conditions, forming sulfonylated aziridines in excellent yields. The Co-based system enjoys several attributes associated with the relatively low cost of cobalt and the wide accessibility of arylsulfonyl azides. Furthermore, it generates stable dinitrogen as the only byproduct.