18618-91-2

Upstream product

• 123-72-8 butyraldehyde 
• 496-03-7 2-ethyl-3-hydroxyhexanal 
• 94-96-2 2-ethyl-1,3-hexane diol 
• 141-75-3 butyryl chloride 

Relevant academic research and scientific papers

Metal-Organic Frameworks Invert Molecular Reactivity: Lewis Acidic Phosphonium Zwitterions Catalyze the Aldol-Tishchenko Reaction

The influence of metal-organic frameworks (MOFs) as additives is herein described for the reaction of n-alkyl aldehydes in the presence of methylvinylketone and triphenylphosphine. In the absence of a MOF, the expected Morita-Baylis-Hillman product, a β-hydroxy enone, is observed. In the presence of MOFs with UMCM-1 and MOF-5 topologies, the reaction is selective to Aldol-Tishchenko products, the 1 and 3 n-alkylesters of 2-alkyl-1,3-diols, which is unprecedented in organocatalysis. The (3-oxo-2-butenyl)triphenylphosphonium zwitterion, a commonly known nucleophile, is identified as the catalytic active species. This zwitterion favors nucleophilic character in solution, whereas once confined within the framework, it becomes an electrophile yielding Aldol-Tishchenko selectivity. Computational investigations reveal a structural change in the phosphonium moiety induced by the steric confinement of the framework that makes it accessible and an electrophile.

Isolation and total synthesis of two novel metabolites from the fissurellid mollusc Scutus antipodes

There is almost no information on natural products from gastropods in the order Vetigastropoda and nothing at all for the superfamily Fissurellidae (keyhole and slit limpets), which are only partially protected from predation by their shell. Extraction of the Australian fissurellid Scutus antipodes yielded two new compounds, scutinin A [D-sorbityl hexakis(p-hydroxybenzoate)] and scutinin B [2-ethylhexane-1,3-bis(p-hydroxybenzoate)] that were identified by spectroscopic analysis and their structures confirmed by total synthesis. The compounds were found to have antimicrobial activity but no fish antifeedant activity.

Trimerization of aliphatic aldehydes to 1,3-diol monoesters catalyzed by Cp*2Sm(thf)2

Aliphatic aldehydes underwent trimerization in the presence of a catalytic amount of Cp*2Sm(thf)2 under ambient conditions to form 1,3- diol monoestcrs in good yields. For example, the reaction of acetoaldehyde catalyzed by Cp*2Sm(thf)2 gave 4-acetoxy-2-butanol (2a) and 3-acetoxy-1- butanol (3a) in 86% yield.

Lithium Tungsten Dioxide Promoted Claisen-Tishchenko Condensation of Aromatic and Aliphatic Aldehydes

Lithium tungsten dioxide, LiWO2, has been shown to be a useful catalyst for effecting the Claisen-Tishchenko condensation of aldehydes under heterogeneous conditions.

SELECTIVE TRIMERIZATION OF ALIPHATIC ALDEHYDES CATALYZED BY POLYNUCLEAR CARBONYLFERRATES

Aliphatic aldehydes undergo a catalytic trimerization to give 1,3-diol monoesters upon treatment with Fe3(CO)12 in pyridine or with Fe3(CO)12-pyridine N-oxide in benzene.Polynuclear carbonylferrates serve as catalyst for this transformation.