446242-92-8

Basic information

• Product Name: (R)-METHYL 1-PHENYLAZIRIDINE-2-CARBOXYLATE
• Synonyms: (R)-METHYL 1-PHENYLAZIRIDINE-2-CARBOXYLATE
• CAS NO: 446242-92-8
• Molecular Formula: C10H11NO2
• Molecular Weight: 0
• Mol File: 446242-92-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-METHYL 1-PHENYLAZIRIDINE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-METHYL 1-PHENYLAZIRIDINE-2-CARBOXYLATE(446242-92-8)
• EPA Substance Registry System: (R)-METHYL 1-PHENYLAZIRIDINE-2-CARBOXYLATE(446242-92-8)

Safety Data

• Hazardous Substances Data: 446242-92-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-METHYL 1-PHENYLAZIRIDINE-2-CARBOXYLATE is used as a chiral building block for the synthesis of various pharmaceuticals. Its unique stereochemical properties make it a valuable component in the development of new drugs and materials.
Used in Agrochemical Industry:
(R)-METHYL 1-PHENYLAZIRIDINE-2-CARBOXYLATE is used as a precursor in the production of various agrochemicals. Its role in creating chiral compounds contributes to the development of effective and targeted agrochemical products.
Used in Organic Synthesis:
(R)-METHYL 1-PHENYLAZIRIDINE-2-CARBOXYLATE is used as a chiral building block for the creation of chiral amino acids, peptides, and other important organic compounds. Its presence in these compounds can influence their reactivity, stability, and overall properties, making it a crucial component in organic synthesis.
Used in Development of New Drugs and Materials:
(R)-METHYL 1-PHENYLAZIRIDINE-2-CARBOXYLATE has potential applications in the development of new drugs and materials. Its unique properties and versatility in organic synthesis make it a promising candidate for further research and development in various fields.

Upstream product

• 111750-22-2 N-phenyl-N-hydroxy-2,2-dimethylpropanamide 
• 292638-85-8 acrylic acid methyl ester 
• 6832-16-2 methyl diazoacetate 
• 91-78-1 1,3,5-triphenylhexahydro-1,3,5-triazine 
• 265093-28-5 2-Methoxycarbonyl-2-dimethylphenylsilyl-1-phenylaziridine 
• 622-37-7 Phenyl azide 
• 586-96-9 Nitrosobenzene 
• 62-53-3 aniline 
• 1428346-14-8 methyl 2-bromo-3-(phenylamino)propanoate 
• 1428345-82-7 (Z)-methyl 2-bromo-3-(phenylamino)acrylate 
• 67-56-1 methanol 
• 109-88-6 magnesium methanolate 
• 446242-99-5 ((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-((S)-1-phenyl-aziridin-2-yl)-methanone 
• 186581-53-3 diazomethane 

Downstream Products

• 1010707-14-8 C₁₉H₁₈BrF₃N₂O₃ 
• 1010707-15-9 C₁₉H₁₈BrF₃N₂O₃ 

Relevant articles and documents

Palladium-catalyzed intermolecular dehydrogenative aminohalogenation of alkenes under molecular oxygen: An approach to brominated enamines

A novel and efficient palladium-catalyzed dehydrogenative aminohalogenation of alkenes with molecular oxygen as the sole oxidant has been developed. This protocol provides a valuable synthetic tool for the assembly of a wide range of brominated enamines under mild conditions, with unprecedented stereoselectivity and exceptional functional group tolerance. This attractive route for the synthesis of brominated enamines is of great significance due to the products' versatile reactivity for further transformations.

AZIRIDINE SYNTHESIS

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

(Chemical Equation Presented) 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 α-branched aldehydes, a domino amidation-redox amination reaction of acrolein, and a three-component reaction for the synthesis of N-arylaziridines.

Nitrile biotransformations for the efficient synthesis of highly enantiopure 1-arylaziridine-2-carboxylic acid derivatives and their stereoselective ring-opening reactions

Catalyzed by the Rhodococcus erythropolis AJ270 whole cell catalyst under very mild conditions, biotransformations of racemic 1-arylaziridine-2- carbonitriles proceeded efficiently and enantioselectively to produce highly enantiopure S-1-arylaziridine-2-c

Bacterial preparation of enantiopure unactivated aziridine-2-carboxamides and their transformation into enantiopure nonnatural amino acids and vic-diamines

Enantiopure (1R,2S)-1-benzyl- and 1-arylaziridine-2-carboxamides were obtained by kinetic resolution of their racemates by Rhodococcus rhodochrous IFO 15564 catalyzed hydrolysis. Several regio- and enantioselective nucleophilic ring openings of (1R,2S)-1-benzylaziridine-2-carboxamide or its LAH-reduced product led to a series of enantiopure products, such as O-methyl-L-serine and some vicinal diamines.

Enzymatic resolution of N-arylaziridine carboxylates

N-Arylaziridine-2-carboxylates have been enzymatically resolved using the lipase from Candida rugosa to afford optically active aziridine carboxylates in moderate to high enantiomeric purity. The absolute configuration of the unknown aziridine carboxylates was assigned as S by chemical correlation.

Asymmetric synthesis of N-aryl aziridines

The reactions of a variety of N-arylhydroxamates as nitrogen transfer reagents to acryloyl derivatives of (-)-8-phenylmenthol, (-)-quinine and (-)-Oppolzer's sultam acting as Michael acceptors was studied. Poor to modest diastereoselection was observed in the formation of aziridines. The absolute structure of one of the pure diastereomers secured from Oppolzer's auxiliary was established by X-ray crystallography and hence the absolute configuration of the derived methyl-N-phenylaziridine-2-carboxylate could be assigned. Whilst only poor facial selectivity was observed for chiral hydroxamic acid prepared from dehydroabietic acid, moderate to good enantioselection of aziridines could be achieved with the chiral quaternary salts based on cinchona alkaloids, especially with that of cinchonine. A model is presented to explain the origin of enantioselection and a mechanism is proposed for the aziridination reaction.

Ring opening reactions of 2-trialkylsilylaziridines

2-Trialkytsilylaziridines do not readily undergo nucleophilic ring opening without electrophilic assistance. In the presence of strong acids protonation at the nitrogen is followed by nucleophitic attack α to the silicon. With non-nucleophilic counterions, the protonated aziridine can be obtained. N-Alkylation gives the aziridinium salt, which also undergoes α-cleavage. However, the presence of a 3-phenyl substituent gives a stable aziridinium salt that undergoes nucleophilic attack β to the silicon. Reaction of 2-trialkylsilylaziridines with trialkylsilyl halides usually leads to α-cleavage, however, desilylation to give the enamine is also observed. Fluorodesilylation of the 2-trialkylsilylaziridine is not straightforward and only occurred readily when a 2-ethoxycarbonyl group was present. Fluorodesilylation followed by attack on a carbonyl was only observed when very dry samples of fluoride ions were employed.

A new synthesis of aziridine-2-carboxylates: Reaction of hexahydro- 1,3,5-triazines or N-methoxymethylanilines with alkyl diazoacetates in the presence of Lewis acid

Aziridine-2-carboxylates were prepared from the reaction of hexahydro- 1,3,5-triazines or N-methoxymethylanilines with alkyl diazoacetates in the presence of Lewis acid catalyst in high yield.

A new synthesis of aziridine-2-carboxylates by reaction of hexahydro-1,3,5-triazines with alkyldiazoacetates in the presence of tin(IV) chloride

Aziridine-2-carboxylates were prepared from the reaction of hexahydro-1,3,5-triazines with alkyldiazoacetates in the presence of Lewis acid catalyst in high yield.