2-allyl-1-tosylaziridine | 404362-16-9

• 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: 2-allyl-1-tosylaziridine
• 英文别名: 1-(4-Methylphenyl)sulfonyl-2-prop-2-enylaziridine
• CAS: 404362-16-9
• 化学式: C₁₂H₁₅NO₂S
• 分子量: 237.323
• InChiKey: CGUUTLHRGNTVRU-UHFFFAOYSA-N

物化性质

• 沸点：
  351.9±35.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-allyl-1-tosylaziridine 在 9-borabicyclo[3.3.1]nonane dimer 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 1,1-Dimethyl-2-(toluene-4-sulfonyl)-octahydro-cyclopenta[c]pyrrole
  参考文献：
  名称：

  Intramolecular cyclization reactions of aziridines with π-nucleophiles

  摘要：

  We have found that aziridines will react with a variety of pi-nucleophiles in intramolecular cyclization reactions to produce nitrogen containing core structures found in a variety of bioactive molecules. These cyclizations are more general and facile than corresponding intermolecular reactions. We have examined the effects of ring size, pi-nucleophile identity and substitution on this reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.009
• 作为产物：
  描述：

  DL-烯丙基甘氨酸甲酯 在 sodium tetrahydroborate 、 三乙胺 、 三苯基膦 、 lithium chloride 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 64.0h， 生成 2-allyl-1-tosylaziridine
  参考文献：
  名称：

  铃木交叉偶联至取代氮丙啶的路线

  摘要：

  我们已经表明，烯烃氮丙啶的铃木交叉偶联反应是合成取代氮丙啶的有效途径。这是应用于含氮丙啶分子的钯偶联反应的第一个例子。该方法是利用有机铜酸盐试剂合成氮丙啶的其他方法的补充。

  DOI：

  10.1016/s0040-4039(01)01903-7

文献信息

• Directed Nickel-Catalyzed Negishi Cross Coupling of Alkyl Aziridines
  作者：Daniel K. Nielsen、Chung-Yang (Dennis) Huang、Abigail G. Doyle

  DOI：10.1021/ja4076716

  日期：2013.9.11

  Herein we report a nickel-catalyzed C-C bond-forming reaction between simple alkyl aziridines and organozinc reagents. This method represents the first catalytic cross-coupling reaction employing a nonallylic and nonbenzylic Csp(3)-N bond as an electrophile. Key to its success is the use of a new N-protecting group (cinsyl or Cn) bearing an electron-deficient olefin that directs oxidative addition

  在这里，我们报告了简单的烷基氮丙啶和有机锌试剂之间的镍催化的 CC 键形成反应。这种方法代表了第一个采用非烯丙基和非苄基 Csp(3)-N 键作为亲电子试剂的催化交叉偶联反应。其成功的关键是使用带有缺电子烯烃的新 N 保护基团（cinsyl 或 Cn），该烯烃可指导氧化加成并促进还原消除。还介绍了与阐明交叉耦合机制有关的研究。
• A tandem process for the synthesis of β-aminoboronic acids from aziridines with haloamine intermediates
  作者：Subin Park、Jangwoo Koo、Weonjeong Kim、Hong Geun Lee

  DOI：10.1039/d2cc00808d

  日期：——

  An unprecedented synthetic strategy is devised to generate β-aminoboronic acids from aziridines via a sequential process involving 1,2-iodoamine formation and radical borylation under light irradiation. A variety of aziridines including multiply substituted aziridines have been successfully employed as synthetic precursors, expanding their synthetic utility compared to previous methods. Mechanistic

  设计了一种前所未有的合成策略，通过涉及在光照射下形成 1,2-碘胺和自由基硼化的顺序过程从氮丙啶生成 β-氨基硼酸。包括多重取代的氮丙啶在内的多种氮丙啶已成功用作合成前体，与以前的方法相比，它们的合成效用得到了扩展。机理研究表明，硼源在硼化步骤和卤胺中间体的形成中起着独特的作用。
• The synthesis of β-N-tosylamino hydroxylamines via the ring opening of N-tosylaziridines and their use in reverse Cope cyclisations
  作者：Ian A O'Neil、J.Chris Woolley、J.Mike Southern、Heather Hobbs

  DOI：10.1016/s0040-4039(01)01744-0

  日期：2001.11

  N-Tosylated aziridines have been found to undergo high yielding and regioselective ring opening with hydroxylamines in diethyl ether in the presence of boron trifluoride diethyl ether complex to give β-N-tosylamino hydroxylamines. Suitable substrates were shown to undergo reverse-Cope cyclisations to give amino functionalised pyrrolidine and piperidine N-oxides.

  已经发现在三氟化硼二乙醚络合物存在下，N-甲苯磺酸化的氮丙啶在二乙醚中与羟胺一起经历高产率和区域选择性的开环，从而得到β- N-甲苯磺酰基氨基羟胺。已显示合适的底物经历反向-Cope环化，得到氨基官能化的吡咯烷和哌啶N-氧化物。
• Aziridine–allylsilane-mediated synthesis of exocyclic γ-amino olefins and azabicyclo[x.y.1]-systems
  作者：David J Lapinsky、Stephen C Bergmeier

  DOI：10.1016/s0040-4020(02)00725-1

  日期：2002.8

  We have shown that connection of C-2 of an allylsilane to a tethered aziridine ring yields exocyclic γ-amino olefins and desilylated azabicyclo[x.2.1]-systems upon cyclization with BF3·OEt2. Furthermore, manipulation of a specific exocyclic γ-amino olefin provided access to an azabicyclo[3.3.1]nonane. This methodology should be useful for the preparation of natural products and pharmacologically active

  我们已经表明，在用BF 3 ·OEt 2环化后，烯丙基硅烷的C -2与束缚的氮丙啶环连接会生成环外γ-氨基烯烃和脱甲硅氮杂双环[ x .2.1]-系统。此外，对特定的环外γ-氨基烯烃的操作提供了访问氮杂双环[3.3.1]壬烷的途径。该方法学对于制备包含这些双环杂环系统的天然产物和药理活性剂应该是有用的。
• 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.