Structure and musk odour: I. Indane derivatives

Beets, M. G. J.; Essen, H. van; Meerburg, W.

doi:10.1002/recl.19580770910

Cited by 14 publications

(1 citation statement)

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“…Beets is the third competitor to appear on the battlefield under the flag of Polak & Schwarz's. His initial 1958 publication on the subject reveals that he had the PFW–Givaudan fight under attentive scrutiny from the very beginning. This article gathers the work done by his team at N.V. Polak & Schwarz's Essencefabricken around 1954, and deals with novel indanic structures.…”

Section: : Celestolidementioning

confidence: 99%

A Chemical History of Polycyclic Musks

David

2020

Chemistry A European J

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Musk odorants are ubiquitous in fine perfumery as well as household products, and are divided into four main families, the nitromusks, the macrocyclic musks, the polycyclic aromatic musks, and the alicyclic musks, following their order of appearance on the perfumery market. This article presents the scientific and industrial adventures during the discovery of the seven commercial polycyclic musks, which invigorated the aroma chemistry corporations during the second half of the 20th century, resulting in relentless competition. Research and development strategies are exposed, and reactivity, analytical, mechanistic, and structure–activity relationships aspects are discussed as well as some biographical elements of the main scientific actors, and some fine perfumery examples are given as illustrations of their use.

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Section: : Celestolidementioning

confidence: 99%

A Chemical History of Polycyclic Musks

David

2020

Chemistry A European J

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Odeur et constitution XVIII. Sur un dérivé indanique à odeur musquée

Ferrero¹,

Helg²

1959

Helvetica Chimica Acta

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Yolumen SLII, Fasciculus VI (19.59) -No. 228 2111 228. Odeur et constitution XVIII1) Sur un dhrivi: indanique a odeur musquhe par C1. Ferrero et R. Helg (26 V l I I 59)Ces derni6res annCes, la synthhse de substances i odeur musquCe a fait l'objet de nombreuses publications provenant de plusieurs groupes independants de chercheurs.Pour un historique des travaux dans ce domaine, nous renvoyons i+L l'excellente revue du sujet prCsentCe par 31. G. J. BEETS A Genhve en mai 795y2).L'analyse des rbsultats dbji acquis nous a incitCs i+L tenter, d&s 1954, la prCparation de nouvelles substances musquCes des types indanique et tktralinique. Les recherches dont nous allons relater un aspect ont CtC men6es -tout B fait incidemment3) -dans la m&me direction que celles entreprises, i la m&me Cpoque, par le groupe de M. G. J.A 507; de palladium), soit selon HUANG-MISLON~~). Les constantes de VII sont :Eb. 80"/0,6 Torr; d : ' = 0,9074; n g = 1,5122; P.C. + 12,8".Le problkme Ctait toutefois loin d'6tre rCsolu; l'adtylation du dimPthy1-1 ,1t-butyl-6-indane (IX) pur, utilisC en excb comme solvant, livrait en effet 8. son tour, u, Dans cette sbrie, l'importance d u solvant est tr&s remarquable pour l'acbtylation. Ici, le chlorure d'ithylkne a bt6 ajoutd au nitrobenzhe pour diminuer le P. C. de ce dernier e t permettre l'opbration k bassc tcmpdrature. u, Rer. deutsch. chem. Ges. 66, 872 (1933) ; rappelons q u e cc catalyseur rdduit aisiment les fonctions carbonyle e t hydroxyle situees en a d'un noyau aromatique, sauf en cas d'empechement st6rique prononcb. 10) J . Amer. chem. SOC. 68, 2487 (1940) ; contrairement aux observations de B. B. ELSNER & I<. J . PARKER, J. chem. SOC. 1957, 594, ccttc mithoclc a donne, dans nos cas, d'excellents rcndements au dbpart des indanones.

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Structure and musk odour: II. Benzene derivatives

Beets

Meerburg

Essen

1959

Recl. Trav. Chim. Pays‐Bas

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A n d e r of simple &nzene derivatives with mu& odour are described.In a recent paper * a series af new indane derivatives with a musk odour was described. In this series the compound with the strongest musk odour was found to be 4acetyl-lf1-dimethyl-6-t~butylindane (I). +It seemed interestinq to investigate whether 6he non-aromatic ring in the indane system is a requirement for the musk odour or ~h e t h e r it only serves as a convenient camier for some of the essential substituents. The latter was found to be the case: 3,5idi-t-butylacetophenone (11; white crystals: melting point: 38.639.0 a), a lower homolague of I in wlhich the nonaromatic ring h-as been opened while the * The compounds described in this paper are the subject of patent appli-

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Structure and musk odour: I. Indane derivatives

Abstract: A series of new indane derivatives with musk odour is described).

Cited by 14 publications

References 5 publications

A Chemical History of Polycyclic Musks

A Chemical History of Polycyclic Musks

Odeur et constitution XVIII. Sur un dérivé indanique à odeur musquée

Structure and musk odour: II. Benzene derivatives

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