31247-34-4

Usage

Uses

Used in Pharmaceutical Industry:
N-Benzyl-2-azetidinemethanol is used as a chiral building block for the synthesis of pharmaceutical compounds, contributing to the development of new drugs with improved efficacy and selectivity. Its role in asymmetric catalysis ensures the production of enantiopure compounds, which is essential for the creation of drugs with desired biological activities and reduced side effects.
Used in Agrochemical Industry:
In the agrochemical sector, N-Benzyl-2-azetidinemethanol serves as a chiral building block for the synthesis of agrochemicals, aiding in the development of more effective and selective pesticides and other agricultural chemicals. The enantiopure compounds produced using N-BENZYL-2-AZETIDINEMETHANOL can enhance the performance of agrochemicals while minimizing potential environmental impacts.
Used in Asymmetric Catalysis:
N-Benzyl-2-azetidinemethanol is utilized as a chiral ligand or organocatalyst in asymmetric catalysis, a process that is vital for the production of enantiopure compounds. Its ability to influence the stereochemistry of chemical reactions allows for the creation of compounds with specific chiral centers, which is crucial in various chemical and pharmaceutical applications.
Used in Organic Chemistry Research:
N-BENZYL-2-AZETIDINEMETHANOL is also used in the field of organic chemistry research, where it contributes to the understanding of stereoselective reactions and the development of new synthetic methodologies. Its applications extend to the exploration of novel chiral catalysts and ligands, further expanding the scope of enantioselective synthesis.

InChI:InChI=1/C11H15NO/c13-9-11-6-7-12(11)8-10-4-2-1-3-5-10/h1-5,11,13H,6-9H2

Upstream product

• 54773-11-4 1-benzylazetidine-2-carboxylic acid ethyl ester 
• 18085-37-5 methyl 1-benzyl-2-azetidinecarboxylate 
• 168263-75-0 tert-butyl 2-(benzyl-(2-hydroxyethyl)amino)-acetate 
• 1269460-91-4 C₁₅H₂₂ClNO₂ 
• 77647-98-4 tert-butyl N-benzylazetidine-2-carboxylate 
• 104-63-2 N-Benzylethanolamine 

Downstream Products

• 174346-82-8 R,S-1-[(1,1-Dimethylethoxy)carbonyl]azetidine-2-methanol 
• 534616-88-1 N-benzylazetidine-2-carbaldehyde 
• 5291-77-0 1-benzyl-2-pyrrolidone 
• 1269461-40-6 C₁₂H₁₄N₄O₂ 
• 1269461-42-8 C₁₃H₁₄N₂O₂ 
• 1269461-14-4 C₁₂H₁₄ClNO₂ 
• 346735-00-0 1-benzylazepane-4-carbonitrile 
• 1256490-90-0 3-(N-benzylpyrrolidin-2-yl)propanenitrile 

Relevant academic research and scientific papers

KRAS G12C INHIBITORS

The present invention relates to compounds that inhibit KRas G12C. In particular, the present invention relates to compounds that irreversibly inhibit the activity of KRas G12C, pharmaceutical compositions comprising the compounds and methods of use therefor.

Targeting Alzheimer's disease by investigating previously unexplored chemical space surrounding the cholinesterase inhibitor donepezil

A series of twenty seven acetylcholinesterase inhibitors, as potential agents for the treatment of Alzheimer's disease, were designed and synthesised based upon previously unexplored chemical space surrounding the molecular skeleton of the drug donepezil, which is currently used for the management of mild to severe Alzheimer's disease. Two series of analogues were prepared, the first looking at the replacement of the piperidine ring in donepezil with different sized saturated N-containing ring systems and the second looking at the introduction of different linkers between the indanone and piperidine rings in donepezil. The most active analogue 5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl 1-benzylpiperidine-4-carboxylate (67) afforded an in vitro IC50value of 0.03 ± 0.07 μM against acetylcholinesterase with no cytotoxicity observed (IC50of >100 μM, SH-SY5Y cell line). In comparison donepezil had an IC50of 0.05 ± 0.06 μM and an observed cytotoxicity IC50of 15.54 ± 1.12 μM. Molecular modelling showed a strong correlation between activity and in silico binding in the active site of acetylcholinesterase.

Ring expansion of 2-(1-Hydroxyalkyl)azetidines to 4-(2-Chloroethyl) oxazolidinones

2-(1-Hydroxyalkyl)azetidines react with bis(trichloromethyl) carbonate (BTC) after basic treatment to afford 4-(2-chloroethyl)oxazolidinones. The scope of this rearrangement was examined in detail and its efficiency was shown to depend on the class of the

NHC-Catalyzed intramolecular redox amidation for the synthesis of functionalized lactams

A very efficient NHC-catalyzed lactamization reaction is reported. For most cases, the ring expansion reaction proceeds to cleanly furnish five- and six-membered N-Ts and N-Bn lactams, without the need for further purification. Evidence is presented suggesting a dual role for the stoichiometric base: (1) deprotonation of the triazolium precatalyst and (2) activation of the nitrogen leaving group through hydrogen bonding.

Azetidine based transition state analogue inhibitors of N-ribosyl hydrolases and phosphorylases

N-Ribosyl phosphorylases and hydrolases catalyze nucleophilic displacement reactions by migration of the cationic ribooxacarbenium carbon from the fixed purine to phosphate and water nucleophiles, respectively. As the lysis reaction progresses along the r

AZETIDINE ANALOGUES OF NUCLEOSIDASE AND PHOSPHORYLASE INHIBITORS

Azetidine analogues of nucleosidase and nucleoside phosphorylase inhibitors having the general formula (I), the use of these compounds as pharmaceuticals, pharmaceutical compositions containing the compounds, methods of treating certain diseases using the compounds, processes for preparing the compounds, and intermediates useful in the preparation of the compounds wherein W and X are each independently selected from hydrogen, CH2OH, CH2OQ and CH2SQ; Y and Z are each independently selected from hydrogen, halogen, CH2OH, CH2OQ, CH2SQ, SQ, OQ and Q; Q is an alkyl, aralkyl or aryl group each of which may be optionally substituted with one or more substituents selected from hydroxy, halogen, methoxy, amino, or carboxy; R1 is a radical of the formula (II) or R1 is a radical of the formula (III) A is selected from N, CH and CR2, where R2 is selected from halogen, alkyl, aralkyl, aryl, OH, NH2, NHR3, NR3R4 and SR5, where R3, R4 and R5 are each alkyl, aralkyl or aryl groups optionally substituted with hydroxy or halogen, and where R2 is optionally substituted with hydroxy or halogen when R2 is alkyl, aralkyl or aryl; B is selected from hydroxy, NH2, NHR6, SH, hydrogen and halogen, where R6 is an alkyl, aralkyl or aryl group optionally substituted with hydroxy or halogen; D is selected from hydroxy, NH2, NHR7, hydrogen, halogen and SCH3, where R7 is an alkyl, aralkyl or aryl group optionally substituted with hydroxy or halogen; E is selected from N and CH; G is a C1-4 saturated or unsaturated alkyl group optionally substituted with hydroxy or halogen, or G is absent; or a tautomer thereof, or a pharmaceutically acceptable salt thereof, or an ester thereof, or a prodrug thereof.

Simple azetidine N-oxides: Synthesis, structure and reactivity

The preparation of two stable azetidine N-oxides is described; one structure was confirmed by X-ray crystallography and the second was found to undergo a quantitative ring expansion to yield a new 6-hydroxy tetrahydro1,2-oxazine, a potentially useful reag