(S)-(3,5-dinitrophenyl)(2-isopropylaziridin-1-yl)methanone | 1335200-11-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-(3,5-dinitrophenyl)(2-isopropylaziridin-1-yl)methanone
• 英文别名: (S)-N-(3,5-dinitrobenzoyl)-2-isopropylaziridine；(3,5-dinitrophenyl)-[(2S)-2-propan-2-ylaziridin-1-yl]methanone
• CAS: 1335200-11-7
• 化学式: C₁₂H₁₃N₃O₅
• 分子量: 279.252
• InChiKey: TVGFPJSIZQPXTD-JTDNENJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-(3,5-dinitrophenyl)(2-isopropylaziridin-1-yl)methanone 在 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以94%的产率得到(4S)-2-(3,5-dinitrophenyl)-4-propan-2-yl-4,5-dihydro-1,3-oxazole
  参考文献：
  名称：

  Phosphine-Catalyzed Heine Reaction

  摘要：

  Aziridines are important synthetic Intermediates which readily undergo ring-opening reactions. It is demonstrated that electron-rich phosphines are efficient catalysts for the regioselective rearrangement of N-acylaziridines to oxazolines. The reactions occur in excellent yield under neutral conditions. Evidence is provided for an addition/elimination mechanism by generation of a phosphonium intermediate. Similar intermediates may be useful for the development of alternate aziridine ring-opening processes and stereoselective synthesis with enantiopure phosphines.

  DOI：

  10.1021/ol202410v
• 作为产物：
  描述：

  (2S)-2-isopropyl-1-[(4-methylphenyl)sulfonyl]aziridine 在 sodium naphthalenide 作用下， 以 乙二醇二甲醚 为溶剂， 反应 12.25h， 生成 (S)-(3,5-dinitrophenyl)(2-isopropylaziridin-1-yl)methanone
  参考文献：
  名称：

  Scalable Synthesis of N-Acylaziridines from N-Tosylaziridines

  摘要：

  N-Acylaziridines are important starting materials for the synthesis of chiral amine derivatives. The traditional methods for producing these activated aziridines have significant drawbacks. The gram scale synthesis of N-acylaziridines by deprotection of N-tosylaztridines and reprotection with N-hydroxysuccinimide derivatives is described. Mono- and disubstituted aziridines perform well, with complete retention of stereochemical purity. The consistently moderate yields are linked to the N-tosylaziridine deprotection step, while acylation with N-hydroxysuccinimide derivatives is highly efficient.

  DOI：

  10.1021/jo401267j

文献信息

• Enantioselective Synthesis and Stereoselective Ring Opening of<i>N</i>-Acylaziridines
  作者：Jennifer Cockrell、Christopher Wilhelmsen、Heather Rubin、Allen Martin、Jeremy B. Morgan

  DOI：10.1002/anie.201204224

  日期：2012.9.24

  Kinetic resolution of N‐acylaziridines by nucleophilic ring opening was achieved with (R)‐BINOL as the chiral modifier under boron‐catalyzed conditions (see scheme; Ar=3,5‐dinitrophenyl). The consumed enantiomer of aziridine can be further converted to an enantioenriched 1,2‐chloroamide with recovery of (R)‐BINOL.

  动力学拆分的Ñ通过亲核开环，用（实现-acylaziridines - [R）-BINOL硼催化的条件下，所述手性改性剂（; Ar为3,5-二硝基苯基参见方案）。消耗的氮丙啶对映体可以进一步转化为对映体富集的1,2-氯酰胺，同时回收（R）-BINOL。