R*R* 2-methoxycarbonyl-3-phenylaziridine | 179092-78-5

• 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: R*R* 2-methoxycarbonyl-3-phenylaziridine
• 英文别名: R*S* 2-methoxycarbonyl-3-phenylaziridine；methyl 2-phenylaziridine-3-carboxylate；Methyl 3-phenylaziridine-2-carboxylate
• CAS: 179092-78-5
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: FCVUIWBWIUKGDX-UHFFFAOYSA-N

物化性质

• 沸点：
  268.6±40.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  48.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  R*R* 2-methoxycarbonyl-3-phenylaziridine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 1.0h， 以82%的产率得到甲基 3-苯基-DL-丙氨酸酯
  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
• 作为产物：
  描述：

  rac-(R,S)-methyl 2,3-dibromo-3-phenylpropanoate 在 氨 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以70%的产率得到R*R* 2-methoxycarbonyl-3-phenylaziridine
  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

• Aziridination of α,β-unsaturated esters by (ethoxycarbonyl)nitrene
  作者：Monica Carducci、Stefania Fioravanti、M.Antonietta Loreto、Lucio Pellacani、Paolo A. Tardella

  DOI：10.1016/0040-4039(96)00681-8

  日期：1996.5

  The reaction of α,β-unsaturated esters with (ethoxycarbonyl)nitrene, generated by α-elimination of NsONHCO2Et using CaO as a base in heterogeneous phase, allowed the preparation of aziridine-1,2-dicarboxylates (2a-e) in good isolated yields (57–72%). The same reaction does not take place using triethylamine instead of CaO, in homogeneous conditions.

  α，β-不饱和酯与（乙氧基羰基）硝烯的反应，是通过在异相中以CaO为碱，通过NsONHCO 2 Et的α消除反应而生成的，可在其中制备氮丙啶1,2,2-二羧酸酯（2a-e）良好的孤立产量（57–72％）。在均匀条件下，使用三乙胺代替CaO不会发生相同的反应。
• Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylates
  作者：Teresa M.V.D Pinho e Melo、Ana L Cardoso、António M.d'A Rocha Gonsalves

  DOI：10.1016/s0040-4020(03)00248-5

  日期：2003.3

  The dehalogenation of 2-halo-3-phenyl-2H-azirine-2-carboxylates is described. Using sodium borohydride and tributyltin hydride 3-phenyl-2H-azirine-2-carboxylates were obtained in moderate yields. The synthesis of a new 2-bromo-2H-azirines with a chiral auxiliary, 10-phenylsulfonylisobornyl 2-bromo-3-phenyl-2H-azirine-2-carboxylate, is reported. Its dehalogenation led to 10-phenylsulfonylisobomyl 2H-azirine-2-carboxylate as single stereoisomer together with the formation of 10-phenylsulfonylisobomyl acetate. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Bouayad, Zoheir; Chanet-Ray, Josette; Ducher, S., Journal of Heterocyclic Chemistry, 1991, vol. 28, # 7, p. 1757 - 1768
  作者：Bouayad, Zoheir、Chanet-Ray, Josette、Ducher, S.、Vessiere, Roger

  DOI：——

  日期：——
• 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.