23040-89-3

Usage

Cyclic organic compound

The compound has a closed, circular structure formed by the atoms in its molecule.

Aziridine ring structure

The compound features a three-membered ring consisting of two carbon atoms and one nitrogen atom, which is characteristic of aziridine compounds.

Starting material in organic synthesis

2,2-dimethyl-3-phenylaziridine is used as a base compound to create more complex organic molecules through various chemical reactions.

Production of pharmaceuticals

The compound is specifically used in the synthesis of chiral compounds, which are important in the development of drugs due to their unique properties and biological activity.

Building block for heterocyclic compounds

2,2-dimethyl-3-phenylaziridine serves as a fundamental component in the creation of complex heterocyclic compounds, which have various applications in medicinal chemistry and materials science.

Ligand in metal-catalyzed reactions

The compound acts as a ligand, a molecule that binds to a metal ion to facilitate or enhance a chemical reaction, particularly in metal-catalyzed processes.

Potential reactivity and toxicity

Due to its chemical properties, 2,2-dimethyl-3-phenylaziridine may pose risks in terms of reactivity and toxicity, necessitating proper handling and storage with appropriate safety precautions.

Upstream product

• 768-49-0 (2-methyl-1-propenyl)-benzene 
• 7103-09-5 4-but-1-enylmagnesium bromide 
• 14491-02-2 2,2-dimethyl-3-phenyl-2H-azirine 

Downstream Products

• 69681-79-4 1-Fluoro-2-phenyl-1,1-dimethylethylamine 
• 69681-78-3 2-Fluoro-2-phenyl-1,1-dimethylethylamine 
• 95964-18-4 N-ethoxycarbonyl-2,2-dimethyl-3-phenylaziridine 
• 95964-20-8 2-methyl-1-phenylprop-2-en-1-ol 
• 1534355-14-0 1-azido-2-methyl-1-phenylpropan-2-amine 

Relevant academic research and scientific papers

Direct and Stereospecific Synthesis of N-H and N-Alkyl Aziridines from Unactivated Olefins Using Hydroxylamine-O-Sulfonic Acids

A RhII-catalyzed direct and stereospecific N-H- and N-alkyl aziridination of olefins is reported that uses hydroxylamine-O-sulfonic acids as inexpensive, readily available, and nitro group-free aminating reagents. Unactivated olefins, featuring a wide range of functional groups, are converted into the corresponding N-H or N-alkyl aziridines in good to excellent yields. This operationally simple, scalable transformation proceeds efficiently at ambient temperature and is tolerant towards oxygen and trace moisture.

Axial ligand modified CO-core bimetallic compound catalyst as well as preparation method and application thereof

The invention discloses an axial ligand modified homonuclear bimetallic compound catalyst and a preparation method and application thereof. The preparation method comprises the steps of making a mixedsystem comprising Rh2 (esp) 2, an axial ligand and organic solvent react at room temperature to obtain the axial ligand modified homonuclear bimetallic compound catalyst, wherein the axial ligand comprises an organic ligand containing an unsaturated nitrogen element. The axial ligand modified homonuclear bimetallic compound catalyst adjusts the reactivity and selectivity of a dinuclear rutheniummetal compound through axial coordination, compared with the method of changing a bridging ligand, the operation method is simpler, the synthesis step is simpler, the reactivity of Rh2(esp)2 is not affected after the coordination, the reaction selectivity of the catalytic synthesis of a N-H heterocyclopropane compound is increased, and the catalyst has universality.

Direct N-H/ N-Me Aziridination of Unactivated Olefins Using O-(Sulfonyl)hydroxylamines as Aminating Agents

Unactivated aziridines are the core substructures in a plethora of bioactive natural products and serve as building blocks in organic synthesis. Despite this, very limited methods are available to access them directly from olefins, as most of the known me

DIRECT STEREOSPECIFIC SYNTHESIS OF UNPROTECTED AZIRIDINES FROM OLEFINS

A method for the direct stereospecific conversion of structurally diverse mono-, di-, tri- and tetra-substituted olefins to N-H, N-alkyl, N-cycloalkyl, or N-aralkyl aziridines using a hydroxylamine amination agent with transition metal catalyst. The method is operationally simple (i.e., one-pot), scalable and fast at ambient temperature.

Direct stereospecific synthesis of unprotected N-H and N-Me aziridines from olefins

Despite the prevalence of the N-H aziridine motif in bioactive natural products and the clear advantages of this unprotected parent structure over N-protected derivatives as a synthetic building block, no practical methods have emerged for direct synthesis of this compound class from unfunctionalized olefins. Here, we present a mild, versatile method for the direct stereospecific conversion of structurally diverse mono-, di-, tri-, and tetrasubstituted olefins to N-H aziridines using O-(2,4-dinitrophenyl)hydroxylamine (DPH) via homogeneous rhodium catalysis with no external oxidants. This method is operationally simple (i.e., one-pot), scalable, and fast at ambient temperature, furnishing N-H aziridines in good-to-excellent yields. Likewise, N-alkyl aziridines are prepared from N-alkylated DPH derivatives. Quantum-mechanical calculations suggest a plausible Rh-nitrene pathway.

HYDROBORATION D'AZIRIDINES ETHYLENIQUES. SYNTHESE D'AZA-1 BICYCLO ALCANES

Hydroboration of aziridines having a β or γ-double bond 3b, 3c, 4b, 7c and 8 yields after oxydation, the expected hydroxy aziridines 11b, 11c, 12b, 13 and 14, which were cyclized by reaction with PPh3/Br2 to give 1-aza bicycloalkanes 23b, 24b, 25c, 26 and 27.The hydroboration of 2-vinyl aziridines 3a, 4a and 7a give Z-allylic amines 16aZ, 17aZ and 18Z.The use of 9-BBN or 2-vinyl substituated aziridines provides the β-hydroxy aziridines 19, 20 and 21.