1256245-84-7

Usage

Uses

Used in Pharmaceutical Industry:
3-[[3,5-bis(trifluoroMethyl)phenyl]aMino]-4-[[(8α,9S)-6'-Methoxycinchonan-9-yl]aMino]3-Cyclobutene-1,2-dione is used as a potential pharmaceutical candidate for [application reason] due to its complex structure and the presence of the cinchona alkaloid moiety, which is known for its pharmacological properties.
Used in Research and Development:
3-[[3,5-bis(trifluoroMethyl)phenyl]aMino]-4-[[(8α,9S)-6'-Methoxycinchonan-9-yl]aMino]3-Cyclobutene-1,2-dione is used as a subject of research and development for [application reason] to explore its potential properties and applications in various fields, including pharmaceuticals and biology.
Note: The specific application reasons are not provided in the materials, so they are left blank. Further information would be needed to fill in these details.

Upstream product

• 130-95-0 quinine 
• 1223105-85-8 3-(3,5-ditrifluoromethylphenylamino)-4-methoxybutane-3-en-1,2-dione 

Relevant academic research and scientific papers

Straightforward enantioselective access to γ-butyrolactones bearing an all-carbon β-quaternary stereocenter

An enantioselective one-pot aldol/lactonization sequence has been developed to access highly challenging γ-butyrolactones bearing an all-carbon quaternary stereocenter at the β-position by reacting acylated succinic esters with aqueous formaldehyde in the presence of 3 mol % loading of a cinchona alkaloid-derived squaramide providing direct access to paraconic acid derivatives in high yield and fairly good level of enantioselectivity (up to 88% ee).

Enantioselective construction of tetrasubstituted stereogenic carbons through bronsted base catalyzed michael reactions: α′-hydroxy enones as key enoate equivalent

Catalytic and asymmetric Michael reactions constitute very powerful tools for the construction of new C-C bonds in synthesis, but most of the reports claiming high selectivity are limited to some specific combinations of nucleophile/electrophile compound types, and only few successful methods deal with the generation of all-carbon quaternary stereocenters. A contribution to solve this gap is presented here based on chiral bifunctional Bronsted base (BB) catalysis and the use of α′-oxy enones as enabling Michael acceptors with ambivalent H-bond acceptor/donor character, a yet unreported design element for bidentate enoate equivalents. It is found that the Michael addition of a range of enolizable carbonyl compounds that have previously demonstrated challenging (i.e., α-substituted 2-oxindoles, cyanoesters, oxazolones, thiazolones, and azlactones) to α′-oxy enones can afford the corresponding tetrasubstituted carbon stereocenters in high diastereo- and enantioselectivity in the presence of standard BB catalysts. Experiments show that the α′-oxy ketone moiety plays a key role in the above realizations, as parallel reactions under identical conditions but using the parent α,β-unsaturated ketones or esters instead proceed sluggish and/or with poor stereoselectivity. A series of trivial chemical manipulations of the ketol moiety in adducts can produce the corresponding carboxy, aldehyde, and ketone compounds under very mild conditions, giving access to a variety of enantioenriched densely functionalized building blocks containing a fully substituted carbon stereocenter. A computational investigation to rationalize the mode of substrate activation and the reaction stereochemistry is also provided, and the proposed models are compared with related systems in the literature.

Highly enantioselective michael addition of nitroalkanes to chalcones using chiral squaramides as hydrogen bonding organocatalysts

A series of squaramide-based organocatalysts were facilely synthesized and applied as hydrogen bonding organocatalysts in the enantioselective Michael addition of nitroalkanes to chalcones. These organocatalysts promoted the Michael addition with low cata