2-β-Naphthyl-aziridin | 21441-74-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-β-Naphthyl-aziridin
• 英文别名: 2-Naphthalen-2-ylaziridine
• CAS: 21441-74-7
• 化学式: C₁₂H₁₁N
• 分子量: 169.226
• InChiKey: BHBPOZKLVWZIMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  21.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-β-Naphthyl-aziridin 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 2-Ethyl-1-methanesulfonyl-2-naphthalen-2-yl-aziridine
  参考文献：
  名称：

  Enantioselective addition of organolithium reagents to a 2H-azirine

  摘要：

  3-(2-Naphthyl)-2H-azirine was used as a model substrate in the first enantioselective addition of organolithium reagents to an azirine. Various organolithium reagents have been used together with different chiral ligands. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00533-5
• 作为产物：
  描述：

  2-(naphthalen-2-yl)-2-[(trimethylsilyl)oxy]acetonitrile 在 氯磺酸 、 lithium aluminium tetrahydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 、 甲苯 、 乙腈 为溶剂， 反应 18.0h， 生成 2-β-Naphthyl-aziridin
  参考文献：
  名称：

  N-未受保护的氮丙啶与 α-氧代烯酮的无催化剂亲电环扩展以有效访问 2-亚烷基-1,3-恶唑烷

  摘要：

  2-(2-氧代亚烷基)-1,3-恶唑烷衍生物通过无催化剂的N-未保护氮丙啶和α-氧代烯酮的烯酮C=O双键的无催化剂亲电子环膨胀，以良好到优异的产率区域特异性地合成，原位由 2-重氮-1,3-二酮的微波辅助沃尔夫重排产生。环膨胀主要经历了 S N 1 过程，氢键决定了产物的 ( E )-构型。

  DOI：

  10.1002/adsc.202100320

文献信息

• Efficient synthesis of ethyl 2-(oxazolin-2-yl)alkanoates via ethoxycarbonylketene-induced electrophilic ring expansion of aziridines
  作者：Yelong Lei、Jiaxi Xu

  DOI：10.3762/bjoc.18.6

  日期：——

  2-(oxazolin-2-yl)alkanoates in good to excellent yields under microwave heating. The method is a convenient and clean reaction without any activators and catalysts and can be also applied in the synthesis of 2-(oxazolin-2-yl)alkanamides and 1-(oxazolin-2-yl)alkylphosphonates.

  2-重氮-3-氧代烷酸烷基酯生成烷氧基羰基烯酮，其与氮丙啶发生亲电扩环，在微波加热下以良好至优异的产率得到 2-(恶唑啉-2-基)烷酸烷基酯。该方法无需任何活化剂和催化剂，简便、清洁反应，还可用于合成2-(恶唑啉-2-基)链烷酰胺和1-(恶唑啉-2-基)烷基膦酸酯。
• Regio- and stereoselective synthesis of thiazoline derivatives <i>via</i> the thioketene-induced ring expansion of aziridines
  作者：Qiuyue Wu、Jiaxi Xu

  DOI：10.1039/d1cc06535a

  日期：——

  Metal-free thioketene-induced ring expansion of aziridines gave 4-alkylthiazolines stereospecifically from 2-alkylaziridines through an intramolecular substitution at the less substituted ring carbon and 5-arylthiazolines stereoselectively from 2-arylaziridines via tandem ring cleavage and formation through intimate ion-pair intermediates after nucleophilic addition of aziridines to thioketenes generated

  无金属硫烯酮诱导的氮丙啶环扩展通过在较少取代的环碳上的分子内取代从 2-烷基氮丙啶立体选择性地得到 4-烷基噻唑啉，通过串联环裂解和通过紧密离子对中间体形成从 2-芳基氮丙啶立体选择性地得到 5-芳基噻唑啉在碱存在下，将氮丙啶亲核加成到由 4-取代的 1,2,3-噻二唑生成的硫代烯酮上。
• Tandem electrocatalytic aziridination – ring expansion of simple aromatic olefins using ammonia and carbon dioxide
  作者：Jef R. Vanhoof、Robin Dirix、Dirk E. De Vos

  DOI：10.1039/d2gc03879j

  日期：——

  olefins with NH3 and CO2 or CS2 in a telescoped sequence is reported, forming 2-oxazolidinones or 2-thiazolidinethiones. The reaction proceeds via a N–H aziridine, which subsequently undergoes ring expansion with CO2 or CS2. Both steps are mediated by the same simple iodide catalyst and total yields of up to 91% referring to the alkene are achieved with excellent regioselectivities. This sustainable

  N-杂环是在有机合成和应用中经常出现的重要结构基序。因此，非常需要使用烯烃等常见起始原料的直接和绿色合成方法。在此，报道了芳香族烯烃与 NH 3和 CO 2或 CS 2以伸缩序列进行无金属电化学偶联，形成 2-恶唑烷酮或 ​​2-噻唑烷硫酮。该反应通过N-H 氮丙啶进行，随后与 CO 2或 CS 2发生扩环. 这两个步骤均由相同的简单碘化物催化剂介导，并且以出色的区域选择性实现了高达 91% 的烯烃总收率。这种使用现成材料的可持续反应具有出色的原子效率，只有 H 2作为潜在有用的副产物。
• 2,4- vs 3,4-Disubsituted Pyrrole Synthesis Switched by Copper and Nickel Catalysts
  作者：Feng Chen、Tao Shen、Yuxin Cui、Ning Jiao

  DOI：10.1021/ol302270z

  日期：2012.9.21

  A novel and efficient copper or nickel catalyzed highly selective denitrogenative annulation of vinyl azides with aryl acetaldehydes has been developed. 2,4- and 3,4-diaryl substituted pyrroles, which are difficult to synthesize by the reported methods, can be highly regioselectively prepared by this protocol simply switched by the selection of the transition metal catalysts. Compared with the reported acidic or basic conditions for polysubstituted pyrrole synthesis, the present reaction conditions are mild, neutral, and very simple without any additives.
• A Formal [3+2] Cycloaddition Process with Nonactivated Aziridines to Polysubstituted Indolizidines
  作者：Wei Zhu、Guorong Cai、Dawei Ma

  DOI：10.1021/ol0513692

  日期：2005.12.1

  [chemical reaction: see text]. Heating a mixture of ethyl 7-iodo-2-heptynoate (or its analogues), 2-aryl aziridines, and K2CO3 in dry CH(3)CN delivers polysubstituted indolizidines. This reaction goes through an S(N)2/formal [3+2] cycloaddition process and represents the first synthetically useful example of the formal [3+2] cycloaddition process through a C-N bond cleavage of nonactivated aziridines.