1-Phenyl-aziridine-2-carboxylic acid tert-butyl ester

• 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: 1-Phenyl-aziridine-2-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 1-phenylaziridine-2-carboxylate
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: GTIBTMMSHONCRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丙烯酸叔丁酯 、 亚硝基苯 在 2-pentafluorophenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 sodium hydride 、 苯甲醛 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到1-Phenyl-aziridine-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  N-Heterocyclic Carbene (NHC)-Catalyzed Direct Amidation of Aldehydes with Nitroso Compounds

  摘要：

  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.

  DOI：

  10.1021/ol8004276

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。
• Synthesis of aziridines by visible-light induced decarboxylative cyclization of N-aryl glycines and diazo compounds
  作者：Yong Liu、Xichang Dong、Guojun Deng、Lei Zhou

  DOI：10.1007/s11426-015-5513-8

  日期：2016.2

  A visible-light induced decarboxylative aza-Darzens reaction between N-aryl glycines and diazo compounds was developed, which affords various mono-substituted aziridines in good yields.

  研究人员开发了一种可见光诱导的 N-芳基甘氨酸与重氮化合物之间的脱羧偶氮-达尔曾反应，该反应能以良好的收率生成各种单取代的氮丙啶类化合物。
• A new enantioselective synthesis of N-arylaziridines by phase-transfer catalysis
  作者：João Aires-de-Sousa、Ana M Lobo、Sundaresan Prabhakar

  DOI：10.1016/0040-4039(96)00490-x

  日期：1996.4

  Chiral N-arylaziridines are obtained from N-acyl-N-arylhydroxylamines using quaternary salts of Cinchona alkaloids as phase-transfer catalysts.

  使用金鸡纳生物碱的季盐作为相转移催化剂，从N-酰基-N-芳基羟胺获得手性N-芳基氮丙啶。
• 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.
• 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.