177260-59-2

Upstream product

• 2189-60-8 Octylbenzene 
• 46745-66-8 1-octyl-4-vinylbenzene 
• 141-43-5 ethanolamine 
• 682-30-4 Diethyl vinylphosphonate 
• 268557-49-9 2-(acetylamino)-2-[2-(4-octylphenyl)-2-oxo-ethyl]propanedioic acid diethyl ester 
• 64068-76-4 α-bromomethyl p(n-octyl)phenyl cetone 
• 162358-08-9 diethyl 2-acetamido-2-[2-(4-octylphenyl)ethyl]malonate 

Downstream Products

• 903894-58-6 N-[1-hydroxymethyl-3-(4-octylphenyl)propyl]-hexadecanamide 
• 903894-74-6 Hexadecanoic acid [3-(4-octyl-phenyl)-1-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-propyl]-amide 
• 241476-97-1 2-[(S)-α-methoxy-α-trifluoromethylphenylacetylamino]-4-(4-octylphenyl)butanol 
• 241476-98-2 2-[(R)-α-methoxy-α-trifluoromethylphenylacetylamino]-4-(4-octylphenyl)butanol 
• 949081-33-8 [1-(di-tert-butoxy-thiophosphoryloxymethyl)-3-(4-octyl-phenyl)-propyl]-carbamic acid tert-butyl ester 
• 949014-01-1 [1-(di-tert-butoxy-phosphoryloxymethyl)-3-(4-octyl-phenyl)-propyl]-carbamic acid tert-butyl ester 
• 596820-24-5 [1-hydroxymethyl-3-(4-octyl-phenyl)-propyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Photocatalytic Hydroaminoalkylation of Styrenes with Unprotected Primary Alkylamines

Catalytic, intermolecular hydroaminoalkylation (HAA) of styrenes provides a powerful disconnection for pharmacologically relevant γ-arylamines, but current methods cannot utilize unprotected primary alkylamines as feedstocks. Metal-catalyzed HAA protocols are also highly sensitive to α-substitution on the amine partner, and no catalytic solutions exist for α-tertiary γ-arylamine synthesis via this approach. We report a solution to these problems using organophotoredox catalysis, enabling a direct, modular, and sustainable preparation of α-(di)substituted γ-arylamines, including challenging electron-neutral and moderately electron-rich aryl groups. A broad range of functionalities are tolerated, and the reactions can be run on multigram scale in continuous flow. The method is applied to a concise, protecting-group-free synthesis of the blockbuster drug Fingolimod, as well as a phosphonate mimic of itsin vivoactive form (by iterative α-C-H functionalization of ethanolamine). The reaction can also be sequenced with an intramolecularN-arylation to provide a general and modular access to valuable (spirocyclic) 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydronaphthyridines. Mechanistic and kinetic studies support an irreversible hydrogen atom transfer activation of the alkylamine by the azidyl radical and some contribution from a radical chain. The reaction is photon-limited and exhibits a zero-order dependence on amine, azide, and photocatalyst, with a first-order dependence on styrene.

Synthesis, stability, and implications of phosphothioate agonists of sphingosine-1-phosphate receptors

Phosphothioates may provide metabolic stability when compared to their phosphate counterparts, while retaining the potency and efficacy as agonists at sphingosine-1-phosphate (S1P) G-protein coupled receptors. Unlike their phosphate precursors, phosphothi