115477-05-9

Upstream product

• 100-46-9 benzylamine 
• 63072-78-6 sorbyl bromide 

Downstream Products

• 115477-28-6 (1RS,2SR,3RS,6SR)-8-benzyl-3-methyl-9-oxo-8-azabicyclo<4.3.0>non-4-ene-2-carboxylic acid 
• 115477-29-7 (1RS,2SR,3SR,6RS)-8-benzyl-2-bromo-3-methyl-9-oxo-8-azabicyclo<4.3.0>non-4-ene-2-carboxylic acid 
• 115477-12-8 (1RS,4SR)-8-benzyl-5-chloro-4-methyl-8-azabicyclo<4.3.0>nona-2,5-dien-7-one 
• 115477-11-7 (1RS,2SR,3RS,6RS)-8-benzyl-1,2-dichloro-3-methyl-9-oxo-8-azabicyclo<4.3.0>non-4-ene-2-carboxylic acid 
• 115477-28-6 (1RS,2SR,3SR,6RS)-8-benzyl-3-methyl-9-oxo-8-azabicyclo<4.3.0>non-4-ene-2-carboxylic acid 
• 115477-18-4 N-Benzyl-N-((2E,4E)-hexa-2,4-dienyl)-acrylamide 
• 122457-66-3 (1RS,4SR)-8-benzyl-5-chloro-4-methyl-8-azabicyclo<4.3.0>non-5-en-7-one 
• 122457-64-1 (3RS,6SR)-8-benzyl-3-methyl-9-oxo-8-azabicyclo<4.3.0>non-1-ene-2-carboxylic acid 
• 115477-22-0 (1RS,4RS,6RS)-8-benzyl-4-methyl-8-azabicyclo<4.3.0>non-2-en-7-one 
• 115477-22-0 (1RS,4RS,6SR)-8-benzyl-4-methyl-8-azabicyclo<4.3.0>non-2-en-7-one 

Relevant academic research and scientific papers

3-Oxo-hexahydro-1H-isoindole-4-carboxylic Acid as a Drug Chiral Bicyclic Scaffold: Structure-Based Design and Preparation of Conformationally Constrained Covalent and Noncovalent Prolyl Oligopeptidase Inhibitors

Bicyclic chiral scaffolds are privileged motifs in medicinal chemistry. Over the years, we have reported covalent bicyclic prolyl oligopeptidase inhibitors that were highly selective for POP over a number of homologous proteins. Herein, we wish to report the structure-based design and synthesis of a novel class of POP inhibitors based on hexahydroisoindoles. A docking study guided the selection of structures for synthesis. The stereochemistry, decoration, and position within the molecule of the bicyclic scaffolds were assessed virtually. Following the synthesis of the best candidates, in vitro assays revealed that one member of this chemical series was more active than any of our previous inhibitors with a Ki of 1.0 nM. Additional assays also showed that the scaffold of this potent inhibitor, in contrast to one of our previously reported chemical series, is highly metabolically stable, despite the foreseen potential sites of metabolism. Interestingly, computer docking calculations accurately predicted the optimal features of the inhibitors.

Chiral gold complex-catalyzed hetero-diels-alder reaction of diazenes: Highly enantioselective and general for dienes

A chiral gold(I) complex-catalyzed highly regio- and enantioselective azo hetero-Diels-Alder reaction has been developed. The chiral gold(I) complex acting as a Lewis acid exhibits high efficiency in the activation of urea-based diazene dienophiles. Moreover, this chiral gold catalyst also rendered a cascade intramolecular enyne cycloisomerization/asymmetric azo-HDA reaction.

Selective N-dealkylation of tertiary amines derived from phenylglycinol or ephedrine family

Tertiary mines bearing an hydroxyethyl group derived from phenylglycinol, norephedrine or norpseudoephedrine can be selectively dealkylated using a two-step sequence involving treatment with thionyl chloride in THF, followed by reaction with an excess of potassium cyanide in THF:DMSO. These conditions are compatible with the presence of an insaturation or a benzyl ether in the substrate.

Synthesis of Hydroisoindoles via Intramolecular Diels-Alder Reactions of Functionalised Amido Trienes

Reactions of amino dienes with acryloyl chloride, maleic anhydride, bromomaleic anhydride, and dichloromaleic anhydride were studied.Acylation and intramolecular reaction by Diels-Alder cyclisation gave bicyclic adducts.Adducts of dichloromaleic anhydride