1-benzyl-2,2-diphenyl-3-fluoroaziridine | 871506-88-6

• 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: 1-benzyl-2,2-diphenyl-3-fluoroaziridine
• 英文别名: 1-benzyl-3-fluoro-2,2-diphenylaziridine；1-Benzyl-2,2-diphenyl-3-fluoroaziridine
• CAS: 871506-88-6
• 化学式: C₂₁H₁₈FN
• 分子量: 303.379
• InChiKey: JIPKWSKSTGSPAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-2,2-diphenyl-3-fluoroaziridine 在 三氟化锑 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 1-benzyl-3-phenyl-1H-indole
  参考文献：
  名称：

  Monofluoro-substituted azomethine ylides in fluorocarbene reactions with imines. Synthesis and transformations of monofluoroaziridines

  摘要：

  N-Arylmethylene and N-benzhydrylideneamines react with fluorocarbene yielding fluoro-substituted azomethine ylides that undergo 1,3-pi-cyclization into aziridines. Generation of fluoroylides in the presence of dipolarophiles (dimethyl maleate or dirnethyl acetylenedicarboxylate) led to the reaction of 1,3-dipolar cycloaddition resulting in substituted 2-pyrrolines or pyrroles. 2-Fluoroaziridines, products of N-alkyl-N-benzhydrylideneamines 1,3-pi-cyclization, in the presence of acid catalysts suffer isomerization into alpha-fluoroimines and 1,3-disubstituted indoles.

  DOI：

  10.1134/s1070428007020224
• 作为产物：
  描述：

  二溴氟甲烷 、 N-(二苯基亚甲基)-1-苯甲胺 在 lead 、 四丁基溴化铵 作用下， 以 二氯甲烷 为溶剂， 以34%的产率得到1-benzyl-2,2-diphenyl-3-fluoroaziridine
  参考文献：
  名称：

  由碳氟化合物产生甲亚胺基团的第一个例子：1,3-环化和1,3-偶极环加成

  摘要：

  席夫碱与氟碳烯的反应是在超声波辐射下，在Bu 4 NBr存在下，用活性铅将二溴氟甲烷与活性铅还原而生成的，涉及形成氟取代的甲亚胺基化物，将其环化成氮丙啶。由苯甲醛的N-芳基丙氨酸生成的酰基的1，3-环化选择性地进行。当在马来酸二甲酯或乙酰二羧酸二甲酯的存在下使席夫碱与氟碳烯反应时，获得了氟取代的偶氮甲亚胺基的1，3-偶极环加成反应成双极性亲和剂的多个键的伯加氢脱氟化氢的产物。在N反应的情况下-苯甲醛的β-烷基亚胺，酰基化物与马来酸二甲酯的环加成反应完全抑制了环化成氮丙啶的过程。

  DOI：

  10.1016/j.tetlet.2005.09.165

文献信息

• Fluoroaziridines as novel substrates in the modified Petasis reaction: synthesis of monofluorinated propargyl amines
  作者：Alexander S. Konev、Sara Stas、Mikhail S. Novikov、Alexander F. Khlebnikov、Kourosch Abbaspour Tehrani

  DOI：10.1016/j.tet.2007.10.067

  日期：2008.1

  Reaction of 2-fluoroaziridines with potassium alkynyltrifluoroborates in the presence of BF3·OEt2 leads to fluorinated propargyl amines in moderate to good yields. The reaction proceeds as an in situ isomerization of 2-fluoroaziridines to α-fluorinated imines, followed by the reaction of the imine with alkynyldifluoroborane, which is generated in situ from the potassium alkynyltrifluoroborates and

  在BF 3 ·OEt 2的存在下，2-氟氮丙啶与炔基三氟硼酸钾的反应以中等至良好的产率生成氟化的炔丙基胺。该反应以2-氟氮丙啶的原位异构化为α-氟化亚胺的方式进行，然后亚胺与炔基二氟硼烷的反应，该炔基二氟硼烷是由炔基三氟硼酸钾和BF 3 ·OEt 2原位生成的。
• The first example of the generation of azomethine ylides from a fluorocarbene: 1,3-cyclization and 1,3-dipolar cycloaddition
  作者：Alexander S. Konev、Mikhail S. Novikov、Alexander F. Khlebnikov

  DOI：10.1016/j.tetlet.2005.09.165

  日期：2005.11

  or dimethyl acetylenedicarboxylate, the products of dehydrofluorination of the primary adducts of the 1,3-dipolar cycloaddition of fluoro-substituted azomethine ylides to multiple bonds of dipolarophiles were obtained. In the case of the reaction of N-alkylimines of benzaldehyde the cycloaddition of ylides to dimethyl maleate completely suppressed the cyclization to aziridines.

  席夫碱与氟碳烯的反应是在超声波辐射下，在Bu 4 NBr存在下，用活性铅将二溴氟甲烷与活性铅还原而生成的，涉及形成氟取代的甲亚胺基化物，将其环化成氮丙啶。由苯甲醛的N-芳基丙氨酸生成的酰基的1，3-环化选择性地进行。当在马来酸二甲酯或乙酰二羧酸二甲酯的存在下使席夫碱与氟碳烯反应时，获得了氟取代的偶氮甲亚胺基的1，3-偶极环加成反应成双极性亲和剂的多个键的伯加氢脱氟化氢的产物。在N反应的情况下-苯甲醛的β-烷基亚胺，酰基化物与马来酸二甲酯的环加成反应完全抑制了环化成氮丙啶的过程。
• A simple route to side-chain fluorinated β-lactams from ring-fluorinated aziridines
  作者：Alexander S. Konev、Mikhail S. Novikov、Alexander F. Khlebnikov、Kourosch Abbaspour Tehrani

  DOI：10.1016/j.jfluchem.2006.10.013

  日期：2007.2

  beta-Lactams bearing a Ph2CF substituent at the C(4)-atorn were synthesized from N-alkyl-2-fluoro-3,3-diphenylaziridines. The transformation was realized using SbF3-mediated isomerization of the monofluoroaziridines to fluorinated aldimines, followed by Staudinger reaction with ketenes. It was shown that this reaction sequence can be performed as a one-pot procedure. (c) 2006 Elsevier B.V. All rights reserved.
• Monofluoro-substituted azomethine ylides in fluorocarbene reactions with imines. Synthesis and transformations of monofluoroaziridines
  作者：A. S. Konev、M. S. Novikov、A. F. Khlebnikov

  DOI：10.1134/s1070428007020224

  日期：2007.2

  N-Arylmethylene and N-benzhydrylideneamines react with fluorocarbene yielding fluoro-substituted azomethine ylides that undergo 1,3-pi-cyclization into aziridines. Generation of fluoroylides in the presence of dipolarophiles (dimethyl maleate or dirnethyl acetylenedicarboxylate) led to the reaction of 1,3-dipolar cycloaddition resulting in substituted 2-pyrrolines or pyrroles. 2-Fluoroaziridines, products of N-alkyl-N-benzhydrylideneamines 1,3-pi-cyclization, in the presence of acid catalysts suffer isomerization into alpha-fluoroimines and 1,3-disubstituted indoles.