(2-methylaziridin-1-yl)(4-nitrophenyl)methanone | 21384-47-4

• 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-methylaziridin-1-yl)(4-nitrophenyl)methanone
• 英文别名: p-nitrobenzoyl-1 methyl-2 aziridine；2-methyl-1-(4-nitro-benzoyl)-aziridine；2-Methyl-1-(4-nitro-benzoyl)-aziridin；1-p-Nitrobenzoyl-2-methylaziridin；(2-Methylaziridin-1-yl)-(4-nitrophenyl)methanone
• CAS: 21384-47-4
• 化学式: C₁₀H₁₀N₂O₃
• 分子量: 206.201
• InChiKey: BCAJWOXROGBHTM-UHFFFAOYSA-N

物化性质

• 熔点：
  81-82 °C(Solv: ligroine (8032-32-4))
• 沸点：
  384.8±25.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  65.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-methylaziridin-1-yl)(4-nitrophenyl)methanone 在 sodium iodide 作用下， 以 丙酮 为溶剂， 生成 4-Methyl-2-<4-nitrophenyl>-2-oxazolidin
  参考文献：
  名称：

  The Isomerization and Dimerization of Aziridine Derivatives. IV

  摘要：

  DOI：

  10.1021/ja01472a033
• 作为产物：
  描述：

  4-硝基苯甲酰氯 、 2-甲基氮丙啶 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以88%的产率得到(2-methylaziridin-1-yl)(4-nitrophenyl)methanone
  参考文献：
  名称：

  Phosphine-Catalyzed Heine Reaction

  摘要：

  Aziridines are important synthetic Intermediates which readily undergo ring-opening reactions. It is demonstrated that electron-rich phosphines are efficient catalysts for the regioselective rearrangement of N-acylaziridines to oxazolines. The reactions occur in excellent yield under neutral conditions. Evidence is provided for an addition/elimination mechanism by generation of a phosphonium intermediate. Similar intermediates may be useful for the development of alternate aziridine ring-opening processes and stereoselective synthesis with enantiopure phosphines.

  DOI：

  10.1021/ol202410v

文献信息

• Action de CF3OF sur des aziridines N-substituees
  作者：M. Seguin、J.C. Adenis、C. Michaud、J.J. Basselier

  DOI：10.1016/s0022-1139(00)82576-2

  日期：1980.3

  Trifluoromethyl hypofluorite reacts with N-substituted aziridines with ring opening and 1, 3-addition of F on nitrogen and OCF3 on carbon. Three R substituents are discussed. With R benzenesulfonyl or chlorine one mole of CF3OF is added and N-fluorobenzenesulfonamides and N-chloro, N-fluoroamine are obtained. With R 4-nitrobenzoyl two moles of CF3OF are added and a N, N-difluoroamine is isolated.

  三氟甲基次萤石与N-取代的氮丙啶反应，其开环且在氮上1，的F加成3，在碳上的OCF 3的加成3。讨论了三个R取代基。与R苯磺酰基或氯一起加入一摩尔的CF 3 OF，得到N-氟苯磺酰胺和N-氯，N-氟胺。与R 4-硝基苯甲酰基一起加入两摩尔的CF 3 OF，并分离出N，N-二氟胺。
• Aziridines. 59. Regioselectivity in nucleophilic Ring Opening of 2-Methylaziridines. Lag of bond making as model for the abnormal opening
  作者：Pen-Yuan Lin、Gunther Bentz、H. Stamm

  DOI：10.1002/prac.19933350105

  日期：——

  The regioselectivity ratio RS = normal : abnormal opening of activated 2-methylaziridines 2 by nucleophiles is found to range from 0.10 to unmeasurable large (only normal opening = substitution at CH2 by strongly basic carbanions). RS is assumed to result from S(N)2 variants differing in the degree to which bond breaking is ahead of bond making including perhaps synchronous S(N)2. Bond breaking will be more ahead for the N-CMe bond. High nucleophilic power pushes bond making toward a synchronous process resulting in great RS. The decrease in RS with acyl activation relative to sulfonyl activation is in accord with a flattening of the nitrogen pyramid (planarization effect). The planarization effect is retained in acidic medium by O-protonation: Rs 0.10 - 0.14 for methanolysis as compared to RS 0.43 for N-protonated sulfonylaziridine 2h. AM1 calculations support the planarization hypothesis. - No indication for SET with trityl anion was found.
• SEGUIN M.; ADENIS J. C.; MICHAUD C.; BASSELIER J. J., J. FLUOR. CHEM., 1980, 15, NO 3, 201-211
  作者：SEGUIN M.、 ADENIS J. C.、 MICHAUD C.、 BASSELIER J. J.

  DOI：——

  日期：——
• BAMBAL, RAMESH B.;KEMMITT, RAYMOND D. W., J. ORGANOMET. CHEM., 362,(1989) N-2, C. 18-20
  作者：BAMBAL, RAMESH B.、KEMMITT, RAYMOND D. W.

  DOI：——

  日期：——