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
• Article Data: 28

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

General Description

(2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one is a chemical compound with a complex structure that includes a trichloromethyl group and a bicyclic ring system. (2R,5S)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one is a derivative of the bicyclic compound bicyclo[3.3.0]octane, with a trichloromethyl substituent at the 2-position and a nitrogen and oxygen heteroatom at the 1 and 3 positions, respectively. The stereochemistry of the compound is specified as (2R,5S), indicating the configuration of the stereocenters. The compound can potentially have applications in medicinal chemistry and drug development due to its unique structure and potential biological activity. Further research and exploration of this compound may reveal its potential uses and properties.

Upstream product

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

Downstream Products

• 29802-22-0 (S)-pyrrolidin-2-carboxylic acid dimethylamide 
• 389127-43-9 (R)-methyl 2-allylpyrrolidine-2-carboxylate 
• 850246-88-7 (S)-2-(methylaminocarbonyl)pyrrolidine-1-carbaldehyde 
• 220200-88-4 (3R,7aS)-7a-methyl-3-(trichloromethyl)tetrahydropyrrolo[1,2-c]oxazol-1(3H)-one 
• 706806-60-2 (R)-2-benzyl-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid 
• 1621436-26-7 tert-butyl (R)-2-((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)-1-oxo-2,5-diazaspiro [3.4]octane-5-carboxylate 
• 129704-91-2 (R)-2-allylpyrrolidine-2-carboxylic acid hydrochloride 
• 42856-71-3 (S)-2-methylpyrrolidine-2-carboxylic acid 
• 112348-45-5 (R)-N-(tert-butoxycarbonyl)-2-allylproline methyl ester 

Relevant articles and documents

The first enantioselective approach to 13a-methyl-14- hydroxyphenanthroindolizidine alkaloids - Synthetic studies towards hypoestestatin 2

The first enantioselective approach to 13a-methyl-14- hydroxyphenanthroindolizidine alkaloids was achieved in six linear steps from phenanthryl alcohol and features a highly substrate-dependent Parham cycloacylation and Seebach's enantioselective alkylation as the key steps. The route is concise, protecting-group free, provides access to all stereoisomers, and works on a gram scale. In addition to the putative structure of hypoestestatin 2, the other three stereoisomers and two structurally related analogues were synthesized, none of which shows identical NMR spectra to those reported for natural hypoestestatin 2, which indicates that further structure revision is required. By using Seebach's stereoselective alkylation and Parham cyclization as key steps, the first strategy for the synthesis of 14-hydroxy-13a-methylphenanthroindolizidine alkaloids was developed. The route is practical (six steps in 30 % overall yield) and adaptable for all stereoisomers. In addition, we demonstrate for the first time that the structure of hypoestestatin 2 was misassigned.

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.

A Designed Approach to Enantiodivergent Enamine Catalysis

The rational design and implementation of enantiodivergent enamine catalysis is reported. A simple secondary amine catalyst, 2-methyl-l-proline, and its tetrabutylammonium salt function as an enantiodivergent catalyst pair delivering the enantiomers of α-functionalized aldehyde products in excellent enantioselectivities. This novel concept of designed enantiodivergence is applied to the enantioselective α-amination, aldol, and α-aminoxylation/α-hydroxyamination reactions of aldehydes.

Enantioselective approach to 13a-methylphenanthroindolizidine alkaloids

The first enantioselective approach to 13a-methylphenanthroindolizidine alkaloids is reported, featuring an efficient stereoselective Seebach's alkylation and Pictet-Spengler cyclization. The proposed and other three most probable structures were ruled out, indicating hypoestestatin 1 needs further assignment.

Preparation method of (R)-1-alkanoyl-2-substituted pyrrolidine-2-formamide and medicinal application of (R)-1-alkanoyl-2-substituted pyrrolidine-2-formamide

The invention discloses (R)-1-alkanoyl-2-substituted pyrrolidine-2-formamide as shown in a general formula (I), a preparation method of a compound, a new application of the compound and a pharmaceutical composition containing the compound in the aspect of inhibiting neuroglial cell inflammation.

1,3-Oxazolidin-5-ones derived from proline as chiral components in the synthesis of predictive enantioselective coupling reagents

1,3-Oxazolidin-5-ones derived from both enantiomers of proline and trichloroacetaldehyde were prepared and applied as an amine component in the synthesis of chiral predictive triazine-based coupling reagents. The reagents were found to be useful in condensations yielding enantiomerically enriched products from racemic substrates.