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Synthesis and Olfactory Properties of a 6'-Silasubstituted "Spiro[4.5]-δ-Damascone"

Synthesis and Olfactory Properties of a 6'-Silasubstituted "Spiro[4.5]-δ-Damascone"

Martin A Lovchik, Philip Kraft

Chemistry. 2017 Apr 3;23(19):4590-4596.

PMID: 28009935

Abstract:

The silicon analogue of the potent spirocyclic δ-damascone odorant 6 was synthesized from allyltrichlorosilane (15) and but-2-en-1-ol (16). The latter was transformed to 3-methylpen-4-enenitrile (11) by Saucy-Marbet reaction with ethoxyethane and subsequent treatment with HONH2 ⋅HCl. The resulting γ,δ-unsaturated nitrile 11 was silylated with 1-allyl-1-chlorosilolane (14), which was prepared from allyltrichlorosilane (15) and the bis-Grignard reagent of 1,4-dichlorobutane. Metathetic ring closure employing the Grubbs I catalyst, followed by DIBAL reduction with non-aqueous work up, Grignard reaction with prop-1-en-1-ylmagnesium bromide, and Attenburrow MnO2 oxidation concluded the synthesis. The target compound was found to be olfactorily related to the spiro[4.5]-δ-damascone lead, but approximately 900 times weaker. In a type of enol Brook rearrangement, it thermally decomposes however to 3,6-dihydro-2H-1,2-oxasilocine (20), which surprisingly is a damascone odorant as well; although, 12 000 times weaker.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP57378684	δ-Damascone		57378-68-4	Price

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