trans-[3-(2-chloro-phenyl)-aziridin-2-yl]-phenyl-methanone | 76336-96-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-[3-(2-chloro-phenyl)-aziridin-2-yl]-phenyl-methanone
• 英文别名: (3-(2-chlorophenyl)aziridin-2-yl)(phenyl)methanone；[(2S,3R)-3-(2-chlorophenyl)aziridin-2-yl]-phenylmethanone
• CAS: 76336-96-4
• 化学式: C₁₅H₁₂ClNO
• 分子量: 257.719
• InChiKey: WFZRIQFYNJVGLG-KGLIPLIRSA-N

物化性质

• 熔点：
  92.5-94.5 °C
• 沸点：
  388.9±42.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  39
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-[3-(2-chloro-phenyl)-aziridin-2-yl]-phenyl-methanone 在 dinitrogen tetraoxide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以95%的产率得到2-氯查耳酮
  参考文献：
  名称：

  A Facile Deamination of Aziridines Using N₂O₄Under Very Mild Conditions

  摘要：

  Various aziridines reacted with N2O4 (2 eq) in the presence of Et3N ( 1 or 2 eq) in dry THF to give the corresponding ethylenes in good to excellent yields at (-23 degrees C or -43 degrees C) in 10 min under Ar.

  DOI：

  10.1080/00397919908086096
• 作为产物：
  描述：

  3-(2-chlorophenyl)-1-phenylpropenone 在 偏二甲肼 、 methyloxirane 作用下， 生成 trans-[3-(2-chloro-phenyl)-aziridin-2-yl]-phenyl-methanone
  参考文献：
  名称：

  Direct Imination of Chalcones with Aminimide; Formation of Aziridines

  摘要：

  DOI：

  10.1055/s-1980-29156

文献信息

• Direct NH-aziridination of α,β-unsaturated ketones
  作者：Jiaxi Xu、Peng Jiao

  DOI：10.1039/b200046f

  日期：2002.6.7

  1-Aryl-α,β-unsaturated ketones were directly aziridinated, N-unsubstituted, in a one-pot reaction with satisfactory yields by N,N′-diamino-1,4-diazoniabicyclo[2.2.2]octane dinitrate, a nitrogen–nitrogen ylide precursor, in the presence of sodium hydride.

  1-芳基-α,β-不饱和酮在氢化钠存在下，由氮-氮亚胺前驱体N,N'-二氨基-1,4-二氮双环[2.2.2]八烷二硝酸盐通过一锅反应直接进行未取代的氮杂环化，获得了令人满意的产率。
• <i>N</i>-Amino-<i>N</i>-methylmorpholinium Salts: Highly Active Aziridination Reagents for Chalcones
  作者：Alan Armstrong、David Carbery、Scott Lamont、Andrew Pape、Richard Wincewicz

  DOI：10.1055/s-2006-950425

  日期：2006.9

  A highly effective aziridination reagent, based on N-methylmorpholine, is reported which effects rapid conversion of chalcones to N-unfunctionalised aziridines at room temperature.

  据报道，一种基于 N-甲基吗啉的高效氮丙啶化试剂可在室温下实现查耳酮快速转化为 N-未官能化氮丙啶。
• Facile preparation of allyl amines and pyrazoles by hydrazinolysis of 2-ketoaziridines
  作者：Gang Chen、Mikio Sasaki、Andrei K. Yudin

  DOI：10.1016/j.tetlet.2005.11.039

  日期：2006.1

  Allyl amines and pyrazoles can be obtained by hydrazinolysis of 2-ketoaziridines. A variety of aziridines, including N-unprotected, N-substituted, as well as bicyclic enamine and aminal type, can be transformed into diversely substituted linear or cyclic products. The hydrazinolysis of homochiral aziridines proceeds without racemization. (c) 2005 Published by Elsevier Ltd.
• Efficient Aziridination of α,β-Unsaturated Ketones with<i>O</i>-(2,4-Dinitrophenyl)-hydroxylamine
  作者：Jin-jia Wang、Jin-hua Lao、Xue-ming Li、Rui-jiong Lu、Hui Miao、Ming Yan

  DOI：10.1080/00397911.2010.541968

  日期：2012.6

  The aziridination of alpha,beta-unsaturated ketones with O-(2,4-dinitrophenyl)-hydroxylamine and tertiary amine was developed. trans-Aziridines were obtained exclusively in good yields. The reaction is proposed to occur via an aminimide intermediate.
• An Amine-Promoted Aziridination of Chalcones
  作者：Yu-Mei Shen、Mei-Xin Zhao、Jiaxi Xu、Yian Shi

  DOI：10.1002/anie.200602586

  日期：2006.12.4