phenyl(3-p-tolylaziridin-2-yl)methanone | 101854-88-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl(3-p-tolylaziridin-2-yl)methanone
• 英文别名: [(2S,3R)-3-(4-methylphenyl)aziridin-2-yl]-phenylmethanone
• CAS: 101854-88-0
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: JGTSFRSZLJAAST-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  phenyl(3-p-tolylaziridin-2-yl)methanone 以 乙醚 为溶剂， 反应 72.33h， 生成 [1-(4-methylphenyl)-3-oxo-3-phenyl-2-(phenylcarbamoylamino)propyl] thiocyanate
  参考文献：
  名称：

  Weber, Fritz Gerd; Liepert, Harald; Koeppel, Hubert, Journal fur praktische Chemie (Leipzig 1954), 1986, vol. 328, # 4, p. 612 - 620

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(4-甲基苯基)-1-苯基-丙-2-烯-1-酮 在 N-甲基吗啉 、 2,4-二硝基苯基羟胺 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以85%的产率得到phenyl(3-p-tolylaziridin-2-yl)methanone
  参考文献：
  名称：

  Efficient Aziridination of α,β-Unsaturated Ketones withO-(2,4-Dinitrophenyl)-hydroxylamine

  摘要：

  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.

  DOI：

  10.1080/00397911.2010.541968

文献信息

• Tertiary amine-promoted enone aziridination: investigations into factors influencing enantioselective induction
  作者：Alan Armstrong、Robert D.C. Pullin、Chloe R. Jenner、Klement Foo、Andrew J.P. White、James N. Scutt

  DOI：10.1016/j.tetasy.2013.11.008

  日期：2014.1

  synthesised (up to 77% ee) via a chiral tertiary amine-promoted nucleophilic aziridination of α,β-unsaturated ketones utilising in situ generated N–N ylides (aminimines). A wide range of chiral tertiary amines were synthesised and evaluated, allowing structure–activity relationships to be drawn. The most efficient promoter for asymmetric aziridination, quinine, was assessed with several enones to ascertain

  通过手性叔胺促进的α，β-不饱和酮的手性叔胺促进的亲核叠氮反应，利用原位生成的N - N酰基化物（氨基胺）合成了反式N-未取代的氮丙啶（至多77％ee ）。合成并评估了多种手性叔胺，从而可以得出结构-活性关系。用几种烯酮评估了不对称叠氮化的最有效启动子奎宁，以确定底物结构对产物ee的影响，而中间肼盐则通过X射线晶体学表征。
• 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。
• Amine-Promoted, Organocatalytic Aziridination of Enones
  作者：Alan Armstrong、Carl A. Baxter、Scott G. Lamont、Andrew R. Pape、Richard Wincewicz

  DOI：10.1021/ol062852v

  日期：2007.1.1

  A novel method is presented using N-N ylides (prepared by in situ amination of a tertiary amine) for the aziridination of a range of enone systems. The amine may be used sub-stoichiometrically, and promising levels of enantioselectivity are observed with quinine as promoter. [reaction: see text].

  提出了一种新的方法，该方法使用NN烷基化物（通过叔胺的原位胺化反应制备）进行一系列烯酮体系的叠氮化。可以亚化学计量地使用胺，并且以奎宁作为促进剂观察到有希望的对映选择性水平。[反应：请参见文字]。
• <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。
• Chiral rare earth metal complex-catalyzed conjugate addition of O-alkylhydroxylamines. An efficient synthetic entry into optically active 2-acyl aziridines
  作者：Xiu Lan Jin、Hiroyasu Sugihara、Kazuhiro Daikai、Hiroki Tateishi、Yong Zhi Jin、Hiroshi Furuno、Junji Inanaga

  DOI：10.1016/s0040-4020(02)00983-3

  日期：2002.10