trans-2-(4-methoxyphenyl)aziridine-3-carboxylic acid amide | 133474-08-5

• 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-(4-methoxyphenyl)aziridine-3-carboxylic acid amide
• 英文别名: (+/-)-trans-3-(p-anisyl)aziridine-2-carboxamide
• CAS: 133474-08-5
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: LJDLLRYQPMQHDT-BDAKNGLRSA-N

物化性质

• 沸点：
  425.2±45.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.19
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.26
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  trans-2-(4-methoxyphenyl)aziridine-3-carboxylic acid amide 在 Rhodococcus rhodochrous IFO 15564 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 对甲氧基苯乙醇
  参考文献：
  名称：

  Enantiopure trans-3-Arylaziridine-2-carboxamides: Preparation by Bacterial Hydrolysis and Ring-Openings toward Enantiopure, Unnatural d-α-Amino Acids

  摘要：

  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.

  DOI：

  10.1021/jo101377j
• 作为产物：
  描述：

  Methyl trans-3-(4-methoxyphenyl)aziridine-2-carboxylate 在 氨 作用下， 以 甲醇 为溶剂， 反应 36.0h， 以95%的产率得到trans-2-(4-methoxyphenyl)aziridine-3-carboxylic acid amide
  参考文献：
  名称：

  Enantiopure trans-3-Arylaziridine-2-carboxamides: Preparation by Bacterial Hydrolysis and Ring-Openings toward Enantiopure, Unnatural d-α-Amino Acids

  摘要：

  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.

  DOI：

  10.1021/jo101377j

文献信息

• Synthesis of .alpha.-halocinnamate esters via solvolytic rearrangement of trichloroallyl alcohols
  作者：William J. Kruper、Albert H. Emmons

  DOI：10.1021/jo00010a027

  日期：1991.5

  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.