Infoscience

Journal article

The Diels-Alder approach to musk odor type arenes

The readily accessible 2-halogeno-1-trimethylsilyloxy-1,3-butadienes, e.g. CH2:CRCR1:CHOSiMe3 (R = H, Me; R1 = F, Cl) react smoothly with MeO2CC.tplbond.CCO2Me to afford 4-halophthalic esters, e.g. I. I (R = H, R1 = Fl) was subsequently converted into the isobenzofuran analog II of phantolide like musk fragrances by Grignard methylation, cyclization, and acetylation. [on SciFinder (R)]

    Keywords: Odor and Odorous substances (musk-like ; isobenzofuran analogs of phantolide ; prepn. of) ; halosilyloxybutadiene Diels Alder acetylenedicarboxylate; halophthalate prepn Grignard methylation; halophenylenebispropanol prepn cyclization; haloisobenzofuran prepn acylation; acylhaloisobenzofuran; isobenzofuran acylhalomethyl; musk odor arene; phan

    Note:

    CAN 118:147337

    26-2

    Biomolecules and Their Synthetic Analogs

    Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.

    Journal

    0040-4020

    written in English.

    762-42-5 Role: RCT (Reactant), RACT (Reactant or reagent) (cyclocondensation of, with halo(silyloxy)butadienes, phthalates from); 63383-46-0P; 146271-51-4P (2-Fluoro-1-trimethylsilyloxy-1,3-butadiene); 146271-52-5P (2-Chloro-1-trimethylsilyloxy-1,3-butadiene); 146271-53-6P; 146271-54-7P; 146271-55-8P; 146271-56-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and Diels-Alder reaction of, with acetylenedicarboxylate, phthalate from); 131-11-3P (Dimethyl phthalate); 58138-38-8P (Dimethyl 4-chlorophthalate); 110706-50-8P (Dimethyl 4-fluorophthalate); 146271-57-0P (Dimethyl 4-fluoro-5-methylphthalate); 146271-58-1P (Dimethyl 4-bromo-5-methylphthalate) Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and Grignard methylation of); 113710-82-0P; 146271-59-2P; 146271-60-5P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and cyclization of, isobenzofuran from); 36045-78-0P; 146271-61-6P; 146271-62-7P; 146271-65-0P; 146271-66-1P; 146271-67-2P; 146271-68-3P; 146271-69-4P; 146271-70-7P; 146271-71-8P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 15323-35-0DP (Phantolide) Role: PREP (Preparation) (prepn. of, by Diels-Alder methodol.); 113710-83-1P; 146271-63-8P; 146271-64-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn., metalation, and acylation of); 4170-30-3 (2-Butenal); 31058-93-2 (2-Bromo-3-methyl-2-butenal); 53175-28-3 (2-Chloro-2-butenal); 63995-82-4 (2-Fluoro-3-methyl-2-butenal); 129601-02-1 (2-Fluoro-2-butenal) Role: RCT (Reactant), RACT (Reactant or reagent) (silylation of)

    Reference

    Record created on 2006-03-03, modified on 2016-08-08

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