4286-49-1

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 20, p. 646, 1955 DOI: 10.1021/jo01123a016

InChI:InChI=1/C4H8N2O4/c7-5(8)3-1-2-4-6(9)10/h1-4H2

Upstream product

• 628-21-7 1,4-Diiodobutane 
• 5029-36-7 1,1,4,4-tetrabromo-1,4-dinitro-butane 
• 110-52-1 1,4-dibromo-butane 
• 60-29-7 diethyl ether 

Downstream Products

• 2580-71-4 succinaldehyde dioxime 
• 5029-36-7 1,1,4,4-tetrabromo-1,4-dinitro-butane 
• 2206-60-2 2,5-dinitro-hexane-1,6-diol 
• 70974-59-3 1,6-Bis-<4-methyl-phenyl>-3,5-dinitro-hexadien-(1,5) 
• 5171-66-4 1,6-Bis-<4-chlor-phenyl>-2,5-dinitro-hexadien-(1,5) 
• 5171-67-5 1,6-Bis-<2-chlor-phenyl>-2,5-dinitro-hexadien-(1,5) 
• 5079-80-1 1,6-Bis-(3-methoxy-4-hydroxy-phenyl)-2,5-dinitro-hexadien-(1,5) 
• 5171-68-6 1,6-Bis-<4-brom-phenyl>-2,5-dinitro-hexadien-(1,5) 
• 7506-07-2 4,7-Bis-(2'-cyanaethyl)-4,7-dinitrodecan-dinitril 
• 5171-69-7 1,6-Bis-<2-brom-phenyl>-2,5-dinitro-hexadien-(1,5) 
• 16098-49-0 1,4-Dinitrosuccinaldehyde bis-p-chlorophenylhydrazone 
• 37630-75-4 (E,E)-2,5-dinitro-1,6-diphenylhexa-1,5-diene 
• 120491-53-4 1,6-dioxo-1,6-diphenyl-2,5-dinitrohexane 
• 7465-52-3 4,7-Bis-(2'-methoxycarbonyl-aethyl)-4,7-dinitrodecan-dicarbonsaeure-dimethylester 

Relevant academic research and scientific papers

Epiquinamide: A Poison That Wasn't from a Frog That Was

In 2003, we reported the isolation, structure elucidation, and pharmacology of epiquinamide (1), a novel alkaloid isolated from an Ecuadoran poison frog, Epipedobates tricolor. Since then, several groups, including ours, have undertaken synthetic efforts to produce this compound, which appeared initially to be a novel, β2-selective nicotinic acetylcholine receptor agonist. Based on prior chiral GC analysis of synthetic and natural samples, the absolute structure of this alkaloid was established as (15,9aS)-1-acetamidoquinolizidine. We have synthesized the (1.R*,9aS*)-isomer (epiepiquinamide) using an iminium ion nitroaldol reaction as the key step. We have also synthesized ent-1 semisynthetically from (-)-lupinine. Synthetic epiquinamide is inactive at nicotinic receptors, in accord with recently published reports. We have determined that the activity initially reported is due to cross-contamination from co-occurring epibatidine in the isolated material.

Cross-linking of starch with bifunctional precursors of nitroalkenes

Granular starch was cross-linked with 1,3-di-O-acetyl-2-nitro-1,3-propanediol (1), 1,3-di-O-pivaloyl-2-nitro-1,3-propanediol (2), 2-nitro-3-O-pivaloyl-1-propene-3-ol (3), 1,3-di-O-acetyl-aci-2-nitro-1,3-propanediol (4), 1,3-di-O-pivaloyl-aci-2-nitro-1,3-propanediol (5) and 1,6-di-O-acetyl-2,5-dinitro-1,6-hexanediol (6). The bifunctional precursors for the nitro-alkenes 1, 2, 3, and 4 were readily synthesized in high yields from nitromethane, paraformaldehyde and acetic anhydride (1, 3) or pivaloyl chloride (2, 4), respectively. The reaction rate for the cross-linking was very high, and for 1 and 3, the reaction reached completion within 1 h (at room temperature). The swelling capacities of the products obtained when starch was cross-linked with precursors for the nitroalkenes 1-4 and 6 were lower in comparison to epichlorohydrin cross-linked starch. These results indicate a high reaction efficiency at low degrees of substitution. Cross-linked 2-nitroalkyl starch ethers were synthesized in a one-pot synthesis by addition of 1 or 3 and 2-nitroalkyl acetates to granular suspensions of starch. Copyright (C) 1998 Elsevier Science Ltd.