35468-97-4

Usage

Synthesis Reference(s)

Synthesis, p. 504, 1979Tetrahedron Letters, 25, p. 3079, 1984 DOI: 10.1016/0040-4039(84)80012-X

InChI:InChI=1/C9H16O2/c1-3-4-5-6-7-8-11-9(2)10/h7-8H,3-6H2,1-2H3/b8-7+

Upstream product

• 108-24-7 acetic anhydride 
• 66-25-1 hexanal 
• 111-71-7 heptanal 
• 869-29-4 1,1-diacetoxy-2-propene 
• 108-22-5 Isopropenyl acetate 
• 75-36-5 acetyl chloride 

Downstream Products

• 1203494-01-2 2-(1-phenylethyl)heptanal 
• 16630-91-4 2-methylheptanal 
• 1509927-92-7 4-pentyl-2-(p-tolyl)thiophene 
• 1203494-08-9 2-(2-cyclohexenyl)heptanal 
• 1203494-12-5 4-formyl-1,3-diphenyl-1-nonyne 
• 1203494-04-5 2-{1-(p-tolyl)ethyl}heptanal 
• 17046-02-5 2-hydroxyheptanal dimer 
• 959-21-7 3,6-dipentyl-[1,4]dioxane-2,5-diol 

Relevant academic research and scientific papers

ALPHA-PENTAFLUOROSUFANYL ALDEHYDES, KETONES AND ACIDS

Compounds of formula (I): are disclosed. In these compounds Y is -CH(OH)-, -CH(NHR6 )-, -C(=0)-, -CH=CHCO- or - formula (II) - and R1 and R2 are hydrogen, OH, alkyl, alkoxy, benzyloxy and aryl, and, when Y is -CH(OH)-, additionally alkenyl or alkynyl. Processes for the production of these compounds are also disclosed.

An efficient route to pentasubstituted phenols

A simple and convenient three-step protocol for the synthesis of pentasubstituted tribromophenols based on the acid-catalyzed Grob-type fragmentation of the bicyclic ketone precursors 8a-e in high overall yield is described. The bicyclic ketones 8a-e were obtained in two steps starting from the Diels-Alder cycloadducts 5a-e of β-substituted vinyl acetates and tetrabromo-5,5-dimethoxycyclopentadiene. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Synthesis and properties of natural occurring α-hydroxyaldehydes

A synthesis for aliphatic α-acetoxyaldehydes 18 is presented. These were converted to free aldehydes 9 by action of hog liver esterase. Aliphatic α-hydroxyaldehydes, recently recognized to be produced in the course of lipid-peroxidation of linoleic and other unsaturated fatty acids, are only stable for short time in solution. They react with amines to give Schiff bases. These are instable, but can be trapped after reduction with NaBH4 to the corresponding amines. Since α-hydroxyaldehydes are produced in the case of lipid peroxidation and were found to stimulate oxidative stress, Schiff base formation might be a physiological important process. α-Hydroxyaldehydes form under physiological conditions mercaptals by reaction with thiols.

REACTIVITY OF RCu,BF3 AND R2CuLi,BF3 TOWARDS ALLYLIC ACETALS AND ETHERS

Organocopper and cuprate reagents associated with Lewis acids, are highly reactive towards allylic acetals and ethers.Displacements of the alkoxy group occurs by SN2' attack according to the various parameters of the reaction.