trans-2-phenylaziridine-3-carboxylic acid amide | 79559-52-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trans-2-phenylaziridine-3-carboxylic acid amide
• 英文别名: trans-(+/-)-3-phenylaziridine-2-carboxamide；(2S,3R)-3-phenylaziridine-2-carboxamide
• CAS: 79559-52-7；88286-06-0；133474-06-3；133474-07-4
• 化学式: C₉H₁₀N₂O
• 分子量: 162.191
• InChiKey: GPBCRRMRLBDOKI-SFYZADRCSA-N

物化性质

• 沸点：
  391.4±41.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  65
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-2-phenylaziridine-3-carboxylic acid amide 在 Rhodococcus erythropolis AJ₂₇₀ 作用下， 以 phosphate buffer 为溶剂， 反应 3.0h， 以47%的产率得到(2R,3S)-(-)-3-phenylaziridine-2-carboxamide
  参考文献：
  名称：

  Nitrile and Amide Biotransformations for the Synthesis of Enantiomerically Pure 3-Arylaziridine-2-carboxamide Derivatives and Their Stereospecific Ring-Opening Reactions

  摘要：

  [Graphics]Catalyzed by Rhodococcus erythropolis AJ270 (whole cell catalyst) under very mild conditions, a number of racemic trans-3-arylaziridine-2-carbonitriles and amides were efficiently transformed into enantiopure 2R,3S-3-arylaziridine2-carboxamides. While the nitrile hydratase exhibits low selectivity against nitrile substrates, the amidase is highly enantioselective toward 2S,3R-3-arylaziridine-2-carboxamides. Upon the treatment with catalytic hydrogenation, amine, or water in the presence of one equivalent of TFA, the resulting aziridine-2-carboxamides underwent highly efficient and stereospecific ring-opening reactions to produce enantiopure (alpha-amino-, alpha,beta-diamino-, and (alpha-amino-beta-hydroxypropanamide derivatives in high yields.

  DOI：

  10.1021/jo701732h
• 作为产物：
  描述：

  3-bromo-1,1,2-trichloro-3-phenylpropene 在 硫酸 、 氨 、 水 作用下， 反应 18.83h， 生成 trans-2-phenylaziridine-3-carboxylic acid amide
  参考文献：
  名称：

  Synthesis of .alpha.-halocinnamate esters via solvolytic rearrangement of trichloroallyl alcohols

  摘要：

  Aryl trichlorovinyl ketones undergo regioselective reduction to the corresponding carbinols with sodium borohydride in alcoholic solvents and are transformed to the (Z)-alpha-chlorocinnamate ester derivatives via an acid-catalyzed allylic rearrangement. Michael addition of ammonia to these ester derivatives affords cis- and/or trans-aziridine amides. The facile rearrangement allows the synthesis of d,l-phenylalanine derived from perchloroethylene and toluene.

  DOI：

  10.1021/jo00010a027

文献信息

• Enantiopure <i>trans</i>-3-Arylaziridine-2-carboxamides: Preparation by Bacterial Hydrolysis and Ring-Openings toward Enantiopure, Unnatural <scp>d</scp>-α-Amino Acids
  作者：Roberto Morán-Ramallal、Ramón Liz、Vicente Gotor

  DOI：10.1021/jo101377j

  日期：2010.10.1

  Several racemic trans-3-arylaziridine-2-carboxamides were prepared and then resolved by Rhodococcus rhodochrous IFO 15564-catalyzed hydrolysis. The resulting enantiopure (2R,3S)-3-arylaziridine-2-carboxamides are adequate substrates to undergo fully stereoselective nucleophilic ring-openings at the C-3 ring position to finally yield enantiopure, unnatural D-alpha-aminocarboxylic acids. Experimental evidence is provided that suggests the fate of the (2S,3R)-3-arylaziridine-2-carboxylic acids concomitantly formed during the resolution processes. In this context, the similar bacterial resolution of racemic 1-arylaziridine-2-carboxamides and -carbonitriles, previously investigated by our research group, has been partially re-examined.
• Synthesis and Reactivity of N-Vinyl-1,2,3-dithiazolimines
  作者：Vladimir N. Yarovenko、Andrey A. Esﾕkov、Pavel A. Kondrashev、Anatolii V. Ignatenko、Igor V. Zavarzin、Lidia G. Vorontsova、Igor P. Sedishev、Mikhail M. Krayushkin、Zoya A. Starikova

  DOI：10.3987/com-05-10390

  日期：——