398489-25-3

Usage

Uses

Used in Pharmaceutical Industry:
3-Hydroxy-3-phenylazetidine-1-carboxylic acid tert-butyl ester is used as a building block in organic synthesis for the development of pharmaceutical products. Its potential pharmacological activities make it a valuable component in the creation of new drugs and therapeutic agents.
Used in Agrochemical Industry:
3-Hydroxy-3-phenylazetidine-1-carboxylic acid tert-butyl ester is also used as a key intermediate in the synthesis of agrochemicals. Its versatility allows for the development of various agrochemical products, contributing to advancements in agriculture and pest control.

Upstream product

• 398489-26-4 tert-butyl 3-oxoazetidine-1-carboxylate 
• 100-59-4 phenylmagnesium chloride 
• 108-86-1 bromobenzene 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 958297-39-7 3-phenylazetidin-3-ol trifluoroacetate 
• 1225439-00-8 3-butoxy-3-phenyl-1-(tert-butoxycarbonyl)-azetidine 
• 1225439-05-3 tert-butyl 3-cyclohexyl-3-hydroxyazetidine-1-carboxylate 
• 1225652-38-9 1-tert-butoxycarbonyl-3-butyryloxy-3-phenylazetidine 
• 1447464-07-4 3-phenyl-3-phenylmethoxyazetidine hydrochloride 
• 1447464-25-6 N-methyl-3-phenyl-3-phenylmethoxyazetidine hydrochloride 
• 1447464-26-7 N-methyl-3-phenyl-3-(4-chlorophenyl)methoxyazetidine hydrochloride 

Relevant academic research and scientific papers

AZETIDINE DERIVATIVE, AND PRODRUG THEREOF

An object of the present invention is to provide a compound useful as a therapeutic or prophylactic drug for a disease involving the immune system, by suppressing a function of immune cells by suppressing proliferation of activated T cells or suppressing production of interferon alpha (IFN-α) by activated plasmacytoid dendritic cells (pDC), particularly an autoimmune disease such as systemic lupus erythematosus (SLE) and lupus nephritis in SLE patients. The present invention provides a compound represented by general formula (I) : [wherein X, R1, R2, R3, R4, R5 and R6 are as described in the description], or a pharmaceutically acceptable salt thereof.

Synthesis of Simple 3,3-Diarylazetidines from N-Boc-3-arylazetidinols Using Friedel-Crafts Arylation Conditions

A synthesis of 3,3-diarylazetidines from N-Boc-3-aryl-3-azetidinols using Friedel-Crafts arylation conditions with AlCl3 is described. A series of substituted diarylazetidines were readily prepared and isolated as the oxalate salts in high yield and high

Oxidative Deconstruction of Azetidinols to α-Amino Ketones

A silver-mediated synthesis of α-amino ketones via the oxidative deconstruction of azetidinols has been developed using a readily scalable protocol with isolated yields up to 80percent. The azetidinols are easily synthesized in one step and can act as protecting groups for these pharmaceutically relevant synthons. Furthermore, mechanistic insights are presented and these data have revealed that the transformation is likely to proceed through the β-scission of an alkoxy radical, followed by oxidation and C-N cleavage of the resulting α-amido radical.

Hydrogen Bonding Phase-Transfer Catalysis with Ionic Reactants: Enantioselective Synthesis of γ-Fluoroamines

Ammonium salts are used as phase-Transfer catalysts for fluorination with alkali metal fluorides. We now demonstrate that these organic salts, specifically azetidinium triflates, are suitable substrates for enantioselective ring opening with CsF and a chiral bis-urea catalyst. This process, which highlights the ability of hydrogen bonding phase-Transfer catalysts to couple two ionic reactants, affords enantioenriched γ-fluoroamines in high yields. Mechanistic studies underline the role of the catalyst for phase-Transfer, and computed transition state structures account for the enantioconvergence observed for mixtures of achiral azetidinium diastereomers. The N-substituents in the electrophile influence the reactivity, but the configuration at nitrogen is unimportant for the enantioselectivity.

Stereoselective Access to Azetidine-Based α-Amino Acids and Applications to Small Peptide Synthesis

Non-natural azetidine-based amino acids (Aze) present interesting features in protein engineering. A simple organometallic route toward unsaturated carboxylic acid precursors is presented. Subsequent metal-catalyzed asymmetric reduction allowed for the sy

Chemodivergent and Stereoselective Access to Fused Isoxazoline Azetidines and Thietanes through [3 + 2]-Cycloadditions

By combining efficient methodologies for the preparation of substituted azetines and thietes with a highly regio- and diastereoselective [3 + 2]-cycloaddition, a straightforward pathway for the synthesis of fused isoxazoline azetidines and thietanes has been designed. With minimal steps and starting from commercial sources, a new library of elaborated architectures was synthesized opening up a new class of molecules with large potential in pharmacology. Finally, a retro [2 + 2]-cycloaddition leading to substituted isoxazoles is described.

Regiodivergent Stereoselective Access to Fused Alkylideneazetidines

Following recent advances in the generalization and simplification of 2H-azetine synthesis, a regiodivergent approach to fused 2- and 3-alkylideneazetines was designed via the intermediate formation of unprecedented vinylazetine structures. Concise sequen

Methods for the Synthesis of Substituted Azetines

Spurred on by the recent emerging interest from the chemical community for unsaturated four-membered heterocycles, an unprecedented approach to nitrogen-containing four-membered rings has been designed. 3,4-Disubstituted 2-azetines were synthesized from c

3-Aryl-3-arylmethoxyazetidines. A new class of high affinity ligands for monoamine transporters

A series of 3-aryl-3-arylmethoxy-azetidines were synthesized and evaluated for binding affinities at dopamine and serotonin transporters. The 3-aryl-3-arylmethoxyazetidines were generally SERT selective with the dichloro substituted congener 7c (Ki = 1.0 nM) and the tetrachloro substituted derivative 7i (Ki = 1.3 nM) possessing low nanomolar affinity for the SERT. The 3-(3,4-dichlorophenyl-3-phenylmethoxyazetidine (7g) exhibited moderate affinity at both DAT and SERT transporters and suggests that substitution of the aryl rings can be used to tune the mononamine transporter affinity.

SUBSTITUTED 5-AMINOTHIENO[2,3-C]PYRIDAZINE-6-CARBOXAMIDE ANALOGS AS POSITIVE ALLOSTERIC MODULATORS OF THE MUSCARINIC ACETYLCHOLINE RECEPTOR M4

In one aspect, the invention relates to substituted 5-aminothieno[2,3-c]pyridazine-6- carboxamide analogs, derivatives thereof, and related compounds, which are useful as positive allosteric modulators of the muscarinic acetylcholine receptor M4 (mAChR M4); synthesis methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating neurological and psychiatric disorders associated with muscarinic acetylcholine receptor dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.