1-cyclohexyl-2-benzoylaziridine | 6372-54-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-cyclohexyl-2-benzoylaziridine
• 英文别名: 1-Cyclohexyl-3-benzoylethylenimin；2-Benzoyl-1-cyclohexyl-ethylenimin；(1-cyclohexyl-aziridin-2-yl)-phenyl ketone；(1-Cyclohexyl-aziridin-2-yl)-phenyl-keton；(1-Cyclohexylaziridin-2-yl)-phenylmethanone
• CAS: 6372-54-9
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: ANQDGDBNBRCBCY-UHFFFAOYSA-N

物化性质

• 熔点：
  61-62 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  343.1±35.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  20.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-cyclohexyl-2-benzoylaziridine 、 甲基三苯基碘化膦 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 以76%的产率得到1-cyclohexyl-2-(1-phenylvinyl)aziridine
  参考文献：
  名称：

  乙烯基氮丙啶的无金属氮杂-克莱森型环扩展：七元N-杂环的快速合成

  摘要：

  通过非活化的乙烯基氮丙啶和炔烃的分子间[5 + 2]环加成反应，已经开发出了一种无金属合成7元氮杂杂环的方法。该方法在温和的反应条件下具有较宽的底物范围，可以以高达92％的高收率提供结构多样的7元N-杂环。

  DOI：

  10.1039/c8ob03029d
• 作为产物：
  描述：

  1-cyclohexyl-3,3-dichloro-4-phenyl-2-azetidinone 在 lithium aluminium tetrahydride 、 三氯化铝 、 sodium hydride 、 二甲基亚砜 作用下， 以 乙醚 为溶剂， 反应 6.0h， 生成 1-cyclohexyl-2-benzoylaziridine
  参考文献：
  名称：

  Rearrangement of 2-Aryl-3,3-dichloroazetidines:  Intermediacy of 2-Azetines

  摘要：

  An easy synthesis of 2-aryl-3,3-dichloroazetidines, a rather unexplored class of azaheterocycles, is described. The title compounds were easily obtained by reduction of the corresponding 4-aryl-3,3dichloro-2-azetidinones with monochloroalane, which in turn were synthesized by a ketene-imine [2 + 2] cycloaddition. The reactivity of 3,3-dichloroazetidines with bases was investigated, yielding 2-[dimethoxy(aryl)methyl]aziridines by ring contraction when treated with sodium methoxide. Furthermore, reacting the 3,3-dichloroazetidines with sodium hydride in DMSO, followed by aqueous workup, afforded 1-alkyl-2-aroylaziridines, by hydrolysis of the intermediate 2-azetines and ring closure of the transient 3-amino-2-chloro-1-phenyl-1-propanone derivatives. Monitoring this reaction in an NMR tube, using sodium hydride in DMSO-d(6),, allowed the characterization of the intermediate strained heterocyclic enamines, i.e., 2-azetines, by H-1 and C-13 NMR.

  DOI：

  10.1021/jo010914j

文献信息

• Ethylene Imine Ketones. VII.¹ Stereochemical Configurations, Absorption Spectra and Reactions with Phenylhydrazine²
  作者：Norman H. Cromwell、Norval G. Barker、Ronald A. Wankel、Phillip J. Vanderhorst、Frank W. Olson、J. Hill Anglin

  DOI：10.1021/ja01147a048

  日期：1951.3
• Metal-free aza-Claisen type ring expansion of vinyl aziridines: an expeditious synthesis of seven membered N-heterocycles
  作者：Deepak Singh、Hyun-Joon Ha

  DOI：10.1039/c8ob03029d

  日期：——

  A metal-free approach for the synthesis of 7-membered aza-heterocycles has been developed by the intermolecular [5 + 2] cycloaddition of non-activated vinylaziridines and alkynes. This method has a broad substrate scope under mild reaction conditions to afford structurally diverse 7-membered N-heterocycles in high yield up to 92%.

  通过非活化的乙烯基氮丙啶和炔烃的分子间[5 + 2]环加成反应，已经开发出了一种无金属合成7元氮杂杂环的方法。该方法在温和的反应条件下具有较宽的底物范围，可以以高达92％的高收率提供结构多样的7元N-杂环。
• Rearrangement of 2-Aryl-3,3-dichloroazetidines:  Intermediacy of 2-Azetines
  作者：Yves Dejaegher、Sven Mangelinckx、Norbert De Kimpe

  DOI：10.1021/jo010914j

  日期：2002.4.1

  An easy synthesis of 2-aryl-3,3-dichloroazetidines, a rather unexplored class of azaheterocycles, is described. The title compounds were easily obtained by reduction of the corresponding 4-aryl-3,3dichloro-2-azetidinones with monochloroalane, which in turn were synthesized by a ketene-imine [2 + 2] cycloaddition. The reactivity of 3,3-dichloroazetidines with bases was investigated, yielding 2-[dimethoxy(aryl)methyl]aziridines by ring contraction when treated with sodium methoxide. Furthermore, reacting the 3,3-dichloroazetidines with sodium hydride in DMSO, followed by aqueous workup, afforded 1-alkyl-2-aroylaziridines, by hydrolysis of the intermediate 2-azetines and ring closure of the transient 3-amino-2-chloro-1-phenyl-1-propanone derivatives. Monitoring this reaction in an NMR tube, using sodium hydride in DMSO-d(6),, allowed the characterization of the intermediate strained heterocyclic enamines, i.e., 2-azetines, by H-1 and C-13 NMR.