1245640-44-1

Basic information

• Product Name: (R)-2-(2,4-dinitrobenzyl)octanal
• Synonyms: (R)-2-(2,4-dinitrobenzyl)octanal
• CAS NO: 1245640-44-1
• Molecular Weight: 308.334
• Mol File: 1245640-44-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (R)-2-(2,4-dinitrobenzyl)octanal(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-(2,4-dinitrobenzyl)octanal(1245640-44-1)
• EPA Substance Registry System: (R)-2-(2,4-dinitrobenzyl)octanal(1245640-44-1)

Safety Data

• Hazardous Substances Data: 1245640-44-1(Hazardous Substances Data)

Upstream product

• 124-13-0 Octanal 
• 3013-38-5 2,4-dinitrobenzyl bromide 

Relevant articles and documents

Photochemical activity of a key donor-acceptor complex can drive stereoselective catalytic α-alkylation of aldehydes

Asymmetric catalytic variants of sunlight-driven photochemical processes hold extraordinary potential for the sustainable preparation of chiral molecules. However, the involvement of short-lived electronically excited states inherent to any photochemical reaction makes it challenging for a chiral catalyst to dictate the stereochemistry of the products. Here, we report that readily available chiral organic catalysts, with well-known utility in thermal asymmetric processes, can also confer a high level of stereocontrol in synthetically relevant intermolecular carbon-carbon bond-forming reactions driven by visible light. A unique mechanism of catalysis is proposed, wherein the catalyst is involved actively in both the photochemical activation of the substrates (by inducing the transient formation of chiral electron donor-acceptor complexes) and the stereoselectivity-defining event. We use this approach to enable transformations that are extremely difficult under thermal conditions, such as the asymmetric α-alkylation of aldehydes with alkyl halides, the formation of all-carbon quaternary stereocentres and the control of remote stereochemistry.

Enantioselective α-benzylation of aldehydes via photoredox organocatalysis

The first enantioselective aldehyde α-benzylation using electron-deficient aryl and heteroaryl substrates has been accomplished. The productive merger of a chiral imidazolidinone organocatalyst and a commercially available iridium photoredox catalyst in the presence of household fluorescent light directly affords the desired homobenzylic stereogenicity in good to excellent yield and enantioselectivity. The utility of this methodology has been demonstrated via rapid access to an enantioenriched drug target for angiogenesis suppression.