10202-75-2

Usage

Uses

A highly diastereoselective synthesis of homoallylic alcohols bearing up to two adjacent quaternary centers was achieved using these polysubstituted allylic reagents.

Synthesis Reference(s)

Synthesis, p. 846, 1985 DOI: 10.1055/s-1985-31362

InChI:InChI=1/C10H16O/c1-4-7-10(11,8-5-2)9-6-3/h4-6,11H,1-3,7-9H2

Upstream product

• 101536-70-3 4-(2-Chloro-propyl)-hepta-1,6-dien-4-ol 
• 3724-55-8 methyl but-3-enoate 
• 107-05-1 3-chloroprop-1-ene 
• 1617-18-1 ethyl 3-butenoate 
• 60-29-7 diethyl ether 
• 556-56-9 allyl iodid 
• 541-41-3 chloroformic acid ethyl ester 
• 201230-82-2 carbon monoxide 
• 96-49-1 [1,3]-dioxolan-2-one 
• 688-61-9 Triallylborane 
• 124-38-9 carbon dioxide 
• 93-89-0 benzoic acid ethyl ester 
• 106-95-6 allyl bromide 
• 300-57-2 allylbenzene 

Downstream Products

• 109-87-5 Dimethoxymethane 
• 86203-45-4 3-(2,2-Dimethoxyethyl)-1,1,5,5-tetramethoxy-3-pentanol 
• 144-62-7 oxalic acid 

Relevant academic research and scientific papers

γ-Substituted Secondary Organoalkaline Compounds and their Chlorinated Precursors: Synthetic Applications

The preparation of γ-functionalised secondary organoalkaline metal compounds starting from methyl 3-chlorobutanoate (obtained by addition of hydrogen chloride to commercially available methyl trans-2-butenoate) is described.Reactions of these metallated compounds with suitable electrophilic reagents leads to a variety of tertiary alcohol derivatives.

Synthesis of compounds of the triallylmethane series based on reactions of triallylborane and derivatives of carbonic acid

An original method was developed for the synthesis of functional derivatives of triallylmethane (CH2=CH-CH2)3C-X (X = OH, NH2, or SCOPh) based on reactions of triallylborane with the corresponding derivatives of carbonic acid (ethylene carbonate, diethylcyanamide, and O,S-dimethyldithio carbonate) at 110-120°C.

α-Regioselective Barbier Reaction of Carbonyl Compounds and Allyl Halides Mediated by Praseodymium

The first utility of praseodymium as a mediating metal in the Barbier reaction of carbonyl compounds with allyl halides was reported in this paper. In contrast to the traditional metal-mediated or catalyzed Barbier reactions, exclusive α-adducts were obta

2,4,9-Triazaadamantanes with “Clickable” Groups: Synthesis, Structure and Applications as Tripodal Platforms

2,4,9-Triazaadamantanes (TRIADs) are promising yet scarcely available, conformationally rigid platforms for potential applications in the design of functional molecules and materials. Here, we report a facile synthesis of various N- and C7-substituted 2,4,9-triazaadamantanes, starting from amines and 4-allylhepta-1,6-dienes. A focus was placed on the synthesis of 2,4,9-triazaadamantanes bearing reactive groups (NH2, propargyl, OH) on the bridge nitrogen atoms, which were then used to decorate the 3D scaffold by hydrazone, triazole, and boronate linkages. A reversible opening of the adamantane cage to the acyclic tris-oxime form was observed for 2,4,9-triazaadamantanes possessing hydroxy-groups on the nitrogen atoms (TRIAD-triols). This process could be controlled by temperature or by complexation of TRIAD-triol with a boronic acid. The structure of 2,4,9-triazaadamantanes and the stereodynamics at the bridge nitrogen atoms were studied by X-ray analysis and DFT calculations.

Ni-Catalyzed Formal Carbonyl-Ene Reaction of Terminal Alkenes via Carbon Dioxide Insertion

Nickel catalyzes the multicomponent coupling reaction of terminal alkenes, carbon dioxide, and organoaluminum reagents, leading to the synthesis of homoallylic alcohols in moderate-to-good yields with excellent regio- and stereoselectivities.

Metal zinc-promoted gem-bisallylation of acid chlorides with allyl chlorides in the presence of chlorotrimethylsilane

Treatment of acid chlorides (2) with allyl chlorides (1) in the presence of zinc dust and a catalytic amount of chlorotrimethylsilane (TMSCl) in THF brought about highly facile and effective coupling to give the corresponding gem-bisallylation products, 4-hydroxy-penta-1,6-dienes (3), in good to excellent yields. These reactions are assumed to proceed through allylzinc intermediates generated in situ.

172. β-Cleavage of Bis(homoallylic) Potassium Alkoxides. Two-Step Preparation of Propenyl Ketones from Carboxylic Esters. Synthesis of ar-Turmerone, α-Damascone, β-Damascone, and β-Damascenone

The transformation of 36 bis(homoallylic) alcohols VII to alkenones IX and X via β-cleavage of their potassium alkoxides VIIa in HMPA has been investigated (cf.Scheme 2).These studies have established an order of β-cleavage for 2-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1,1-dimethyl-2-propenyl, and benzyl groups in alkoxides 49a-56a and have allowed a comparison between the β-cleavage reaction and the oxy-Cope rearrangement in alkoxides 74a-83a.As illustrative synthetic applications, a two-step preparation of propenyl ketones 15-42 from carboxylic esters is described, together with syntheses of ar-turmerone (48), α-damascone ((E)-71), β-damascone ((E)-109), and β-damascenone ((E)-111).

Syntheses with Aliphatic Dialdehydes, XXXVII. Synthesis, Structure, and Properties of a Decamethinium Cyanine Dye with Indoline End Groups

The reaction of the trisaldehyde trisacetal 4 with 1,3,3-trimethyl-2-methyleneindoline (7) and its tetrafluoroborate 8 yields either the δ-substituted heptamethinium cyanine dye 9 or the decamethinium cyanine dye 10, depending on the reaction conditions.Configuration and conformation of both polymethine dyes have been determined by means of spectroscopic data as well as by X-ray analyses. - The UV/Vis-spectroscopic "trimethine shift" of trinuclear, Y-conjugated, methinylogous guanidinium ions is compared with the "vinylene shift" of dinuclear, linear-conjugated, vinylogous amidinium ions (Table 1).

REACTIONS OF TITANOCENE ALLYLS

Cp2Tiη3-allyl and Cp2Tiη3-1-methylallyl react with carbon dioxide, phenylisocyanate, benzalaniline, acetone and acetonitrile to give insertion products which are formed via allyl migration.Normal insertion is observed with 2,6-xylylisocyanide.C

FRAGMENTATION OF HOMOALLYLIC ALKOXIDES. SYNTHESIS OF PROPENYL and 2-METHYLPROPENYL KETONES FROM CARBOXYLIC ESTERS

An efficient two-step synthesis of propenyl and 2-methylpropenyl ketones from carboxylic esters is described which uses as the key step the fragmentation of a potassium dihomoallylic alkoxide under mild thermolytic conditions.