(+/-)-1-phenylaziridine-2-carbonitrile | 4916-27-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (+/-)-1-phenylaziridine-2-carbonitrile
• 英文别名: 2-cyano-1-phenylaziridine；1-phenyl-aziridine-2-carbonitrile；1-phenylaziridine-2-carbonitrile；1-Phenyl-aziridin-2-carbonitril；1-Phenyl-2-cyan-aziridin
• CAS: 4916-27-2；928154-94-3
• 化学式: C₉H₈N₂
• 分子量: 144.176
• InChiKey: IYMCVLZZMRFIDE-UHFFFAOYSA-N

物化性质

• 沸点：
  80-90 °C(Press: 0.08 Torr)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  26.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-1-phenylaziridine-2-carbonitrile 在 palladium on activated charcoal potassium phosphate buffer 、 Rhodococcus erythropolis AJ₂₇₀ cells 、 氢气 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 69.92h， 生成 色氨酸杂质
  参考文献：
  名称：

  Nitrile Biotransformations for the Efficient Synthesis of Highly Enantiopure 1-Arylaziridine-2-carboxylic Acid Derivatives and Their Stereoselective Ring-Opening Reactions

  摘要：

  Catalyzed by the Rhodococcus erythropolis AJ270 whole cell catalyst under very mild conditions, biotransformations of racemic 1-arylaziridine-2-carbonitriles proceeded efficiently and enantioselectively to produce highly enantiopure S-1-arylaziridine-2-carboxamides and R-1-arylaziridine-2-carboxylic acids in excellent yields. Although the nitrile hydratase exhibits no selectivity against all nitrile substrates, the amidase is highly R-enantioselective towards 1-arylaziridine-2-carboxamides. When treated with benzyl bromide, 1-phenylaziridine-2S-carboxamide underwent a highly regioselective and enantiospecific ring-opening reaction to afford an almost quantitative yield of R-beta-[(benzyl)phenylamino]-alpha-bromopropanamide (C-2 attack) and R-alpha-[(benzyl)phenylamino]-beta-bromopropanamide (C-3 attack) in a 10.5:1 ratio. Further treatment of the resulting ring-opening products with an N-nucleophilic reagent such as amine and azide led to, through most probably the aziridinium intermediate, the formation of S-alpha-substituted-beta-[(benzyl)phenylamino]propanamides in good chemical yields with high enantiomeric purity.

  DOI：

  10.1021/jo062339v
• 作为产物：
  描述：

  2-chloro-3-(phenylamino)propanenitrile 在 苄基三乙基氯化铵 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以83%的产率得到(+/-)-1-phenylaziridine-2-carbonitrile
  参考文献：
  名称：

  Rao, S.Appa; Kumar, A.; Ila, H., Synthesis, 1981, # 8, p. 623 - 625

  摘要：

  DOI：

文献信息

• [EN] AZIRIDINE SYNTHESIS<br/>[FR] SYNTHÈSE D'AZIRIDINE
  申请人：AGENCY SCIENCE TECH & RES

  公开号：WO2009096907A1

  公开（公告）日：2009-08-06

  The invention relates to a process for making an aziridine, wherein an aldehyde, a nitroso compound and a Michael acceptor are reacted in the presence of an N-heterocyclic carbene (NHC) catalyst.

  该发明涉及一种制备环氮丙烷的方法，其中在N-杂环卡宾（NHC）催化剂的存在下，醛、亚硝基化合物和迈克尔受体发生反应。
• N-Heterocyclic Carbene (NHC)-Catalyzed Direct Amidation of Aldehydes with Nitroso Compounds
  作者：Fong Tian Wong、Pranab K. Patra、Jayasree Seayad、Yugen Zhang、Jackie Y. Ying

  DOI：10.1021/ol8004276

  日期：2008.6.1

  NHC-catalyzed direct amidation of aldehydes with nitroso compounds is a powerful method for the synthesis of N-arylhydroxamic acids. A variety of aryl, alkyl, alkenyl, and heterocyclic aldehydes were found to give excellent yields of the corresponding N-arylhydroxamic acids. This chemistry was also extended to the synthesis of chiral N-arylhydroxamic acids by kinetic resolution of a-branched aldehydes, a domino amidation-redox amination reaction of acrolein, and a three-component reaction for the synthesis of N-arylaziridines.
• Apparao, S.; Singh, G.; Ila, H., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 1, p. 15 - 17
  作者：Apparao, S.、Singh, G.、Ila, H.、Junjappa, H.

  DOI：——

  日期：——
• RAO, S. A.;KUMAR, A.;ILA, H.;JUNJAPPA, H., SYNTHESIS, BRD, 1981, N 8, 623-625
  作者：RAO, S. A.、KUMAR, A.、ILA, H.、JUNJAPPA, H.

  DOI：——

  日期：——
• AZIRIDINE SYNTHESIS
  申请人：Patra Pranab K.

  公开号：US20110112310A1

  公开（公告）日：2011-05-12

  The invention relates to a process for making an aziridine. wherein an aldehyde, a nitroso compound and a Michael acceptor are reacted in the presence of an N-heterocyclic carbene (NHC) catalyst.