118916-60-2

Basic information

• Product Name: (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one
• CAS NO: 118916-60-2
• Molecular Weight: 244.505
• Mol File: 118916-60-2.mol

Chemical Properties

• CAS DataBase Reference: (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one(118916-60-2)
• EPA Substance Registry System: (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one(118916-60-2)

Safety Data

• Hazardous Substances Data: 118916-60-2(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
(2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one is used as a potential candidate in medicinal chemistry for its unique structure and potential biological activity. Its trichloromethyl group and bicyclic ring system may contribute to its interaction with biological targets, making it a promising compound for further research and development.
Used in Drug Development:
In the field of drug development, (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one is utilized as a starting point for the design and synthesis of new pharmaceutical agents. Its specific stereochemistry and functional groups may allow for targeted modifications to enhance its therapeutic potential and selectivity for specific diseases or conditions.

Upstream product

• 302-17-0 chloral hydrate 
• 147-85-3 L-proline 
• 75-87-6 chloral 
• 515-83-3 chloral ethyl hemiacetal 

Downstream Products

• 29802-22-0 (S)-pyrrolidin-2-carboxylic acid dimethylamide 
• 850246-88-7 (S)-2-(methylaminocarbonyl)pyrrolidine-1-carbaldehyde 
• 1196880-41-7 C₁₆H₁₈Cl₃NO₃ 
• 1196880-43-9 (3R,3'R,7aR)-3,3'-bis(trichloromethyl)tetrahydro-1H,1'H-7a,7'a-bipyrrolo[1,2-c]oxazole-1,1'(3H,3'H,5H,5'H)-dione 
• 112348-45-5 (R)-N-(tert-butoxycarbonyl)-2-allylproline methyl ester 
• 42856-71-3 (S)-2-methylpyrrolidine-2-carboxylic acid 
• 220060-08-2 methyl (S)-2-methylpyrrolidine-2-carboxylate monohydrochloride 
• 869001-98-9 dibenzyl N-benzyloxycarbonyl-glycyl-L-2-allylprolyl-L-glutamate 
• 915958-44-0 dibenzyl (2S,5'R)-2-[1'-(2''-benzyloxycarbonylamino-acetyl)-8'-hydroxy-6'-oxo-1',7'-diazaspiro[4.4]non-7'-yl]-pentanedioate 
• 869001-96-7 dibenzyl N-benzyloxycarbonyl-glycyl-L-2-ethylprolyl-L-glutamate 
• 869002-11-9 dibenzyl (2S,5'R)-2-[1'-(2''-benzyloxycarbonylamino-acetyl)-6'-oxo-1',7'-diazaspiro[4.4]non-7'-yl]-pentanedioate 
• 869002-01-7 di-tert-butyl N-tert-butyloxycarbonyl-glycyl-L-2-benzylprolyl-L-glutamate 
• 869001-88-7 N-benzyloxycarbonyl-glycyl-L-2-allylproline 

Relevant articles and documents

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Design and stereoselective synthesis of ProM-2: A spirocyclic diproline mimetic with polyproline type II (PPII) helix conformation

With the aim of developing polyproline type II helix (PPII) secondary-structure mimetics for the modulation of prolin-rich-mediated protein-protein interactions, the novel diproline mimetic ProM-2 was designed by bridging the two pyrrolidine rings of a diproline (Pro-Pro) unit through a Z-vinylidene moiety. This scaffold, which closely resembles a section of a PPII helix, was then stereoselectively synthesized by exploiting a ruthenium-catalyzed ring-closing metathesis (RCM) as a late key step. The required vinylproline building blocks, that is, (R)-N-Boc-2-vinylproline (Boc=tert-butyloxycarbonyl) and (S,S)-5-vinylproline-tert-butyl ester, were prepared on a gram scale as pure stereoisomers. The difficult peptide coupling of the sterically demanding building blocks was achieved in good yield and without epimerization by using 2-(1H-7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU)/N,N-diisopropylethylamine (DIPEA). The RCM proceeded smoothly in the presence of the Grubbs II catalyst. Stereostructural assignments for several intermediates were secured by X-ray crystallography. As a proof of concept, it was shown that certain peptides containing ProM-2 exhibited improved (canonical) binding towards the Ena/VASP homology 1 (EVH1) domain as a relevant protein interaction target.

Synthesis and crystal structure of 6-Trichloromethyl-9-oxa-5-azatricyclo[6. 2.1.01,5]undecan-10-one

6-Trichloromethyl-9-oxa-5-azatricyclo[6.2.1.01,5]undecan-10-one was prepared and its structure clearly established from spectroscopic data and X-ray crystallography. The crystal structure belongs to the orthorhombic system, space group P212121 with a = 8.4494(17), b = 9.3505(19), c = 15.315(3) A , α = β = γ = 90 °, V = 01210.0(4) A 3, Z = 4, Flack = 0.00(10). The absolute configuration of the title compound was determined as (1R,6R).

A Designed Approach to Enantiodivergent Enamine Catalysis

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