10202-75-2

Basic information

• Product Name: 4-ALLYL-1,6-HEPTADIEN-4-OL
• Synonyms: Triallylcarbinol;4-ALLYL-1,6-HEPTADIEN-4-OL;4-ALLYL-1,6-HEPTADIENE-4-OL;AKOS BB-2867;4-Allyl-1,6-heptadien0-4-ol;4-Allylhepta-1,6-dien-4-ol;4-prop-2-enylhepta-1,6-dien-4-ol
• CAS NO: 10202-75-2
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23
• Product Categories: monomer
• Mol File: 10202-75-2.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 218.1°Cat760mmHg
• Flash Point: 82.7°C
• Appearance: /
• Density: 0.862g/cm³
• Vapor Pressure: 0.0272mmHg at 25°C
• Refractive Index: 1.468
• PKA: 14.77±0.29(Predicted)
• Water Solubility: Soluble in water.
• CAS DataBase Reference: 4-ALLYL-1,6-HEPTADIEN-4-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ALLYL-1,6-HEPTADIEN-4-OL(10202-75-2)
• EPA Substance Registry System: 4-ALLYL-1,6-HEPTADIEN-4-OL(10202-75-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-41
• Safety Statements: 26-36/37/39-39
• Hazardous Substances Data: 10202-75-2(Hazardous Substances Data)

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

• 201230-82-2 carbon monoxide 
• 300-57-2 allylbenzene 
• 124-38-9 carbon dioxide 
• 18760-02-6 allyldiethylaluminium 
• 93-89-0 benzoic acid ethyl ester 
• 106-95-6 allyl bromide 
• 98-88-4 benzoyl chloride 
• 107-05-1 3-chloroprop-1-ene 
• 96-49-1 [1,3]-dioxolan-2-one 
• 688-61-9 Triallylborane 
• 60-29-7 diethyl ether 
• 556-56-9 allyl iodid 
• 541-41-3 chloroformic acid ethyl ester 
• 1617-18-1 ethyl 3-butenoate 

Downstream Products

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

Relevant articles and documents

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.

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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.

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.