Acide 3-F-heptylaziridine 2-carboxylique | 150759-05-0

• 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: Acide 3-F-heptylaziridine 2-carboxylique
• 英文别名: 3-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,7-pentadecafluoroheptyl)aziridine-2-carboxylic acid
• CAS: 150759-05-0
• 化学式: C₁₀H₄F₁₅NO₂
• 分子量: 455.123
• InChiKey: KIBSKRGRUFWNPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  59.24
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Acide 3-F-heptylaziridine 2-carboxylique 在 盐酸 作用下， 以76%的产率得到Acide 3-F-heptyl 3-amino 2-chloropropanoique
  参考文献：
  名称：

  Synthese et reactivite de nouveaux synthons perfluoroalkyles. comportement atypique des azirines et aziridines F-alkylees.

  摘要：

  F-alkyl chains perturb the reactivity of substrates in an often unpredictable way. F-alkyl azirine and aziridine carboxylates were prepared from F-alkynylesters, in 80 and 60% yield, respectively, and were found to display reactivities different from those of their hydrocarbon analogs. Thus, F-alkylazirines (5) give addition products easily but resist ring opening, while the F-alkylaziridines (8) are extremely stable, both towards nucleophilic and electrophilic reagents and irrespective of the medium used, neutral, acid or basic.

  DOI：

  10.1016/s0040-4020(01)81291-6
• 作为产物：
  描述：

  3-Pentadecafluoroheptyl-aziridine-1,2-dicarboxylic acid diethyl ester 在 三氟化硼乙醚 、 sodium ethanolate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 6.0h， 生成 Acide 3-F-heptylaziridine 2-carboxylique
  参考文献：
  名称：

  Synthese et reactivite de nouveaux synthons perfluoroalkyles. comportement atypique des azirines et aziridines F-alkylees.

  摘要：

  F-alkyl chains perturb the reactivity of substrates in an often unpredictable way. F-alkyl azirine and aziridine carboxylates were prepared from F-alkynylesters, in 80 and 60% yield, respectively, and were found to display reactivities different from those of their hydrocarbon analogs. Thus, F-alkylazirines (5) give addition products easily but resist ring opening, while the F-alkylaziridines (8) are extremely stable, both towards nucleophilic and electrophilic reagents and irrespective of the medium used, neutral, acid or basic.

  DOI：

  10.1016/s0040-4020(01)81291-6

文献信息

• Stabilite et reactivite anormales des perfluoroalkyl azirines et aziridines
  作者：Mustapha Haddach、Raphaël Pastor、Jean G Riess

  DOI：10.1016/s0040-4039(00)88896-6

  日期：1990.1

  The presence of an F-alkyl chain induces particular reactivity and stability in azirinic and aziridinic rings. The newly synthesized F-alkyl azirine carboxylates undergo addition reactions. The F-alkyl aziridine carboxylates are extremely stable towards both nucleophilic and electrophilic reactants, whether the medium be neutral, acidic or basic.

  F-烷基链的存在在叠氮和叠氮环中引起特别的反应性和稳定性。新合成的F-烷基叠氮基羧酸盐发生加成反应。无论介质是中性，酸性还是碱性，F-烷基氮丙啶羧酸盐对亲核和亲电反应物都极为稳定。