NITRO MUSKS. III.<sup>1</sup> ASYMMETRICAL MUSKS OF THE DINITRO-tert-BUTYL-m-XYLENE SERIES

Carpenter, M. S.; Easter, W. M.

doi:10.1021/jo01366a015

Cited by 16 publications

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“…1:4). UV (Et,O): 222 (4,41),232 (sh,4,36), 279 (4,15). IR (CHCI,): 3000, 2940(CHCI,): 3000, , 1635(CHCI,): 3000, , 1595(CHCI,): 3000, , 1485(CHCI,): 3000, , 1465(CHCI,): 3000, , 1450(CHCI,): 3000, , 1440(CHCI,): 3000, , 1270(CHCI,): 3000, , 1120(CHCI,): 3000, , 1095(CHCI,): 3000, , 1080(CHCI,): 3000, , 1020.…”

Section: ' )unclassified

“…IR (CHCI,): 3010,2970(CHCI,): 3010, ,2940(CHCI,): 3010, , 1660(CHCI,): 3010, , 1595(CHCI,): 3010, , 1485(CHCI,): 3010, , 1290(CHCI,): 3010, , 1120(CHCI,): 3010, , 1085(CHCI,): 3010, , 1015. 'H-NMR (200 MHz, CDC13)7)8): 2,14, 2,24, 2,27 (je s, CH3-C(2'),CH,-C(3'),CH,-C(5')); 3,79,3,89 (ie s, 2 CH,O); 6,36,6,84 (AB, 3J = 8,8, H-C(6), H-C(5)); 6,70 (s, H-C(6)); 7,21, 7,52 (AB, 'J = 8,7, H-C(a), H-C(a')); 7,24 (s, H-C(4) Schmp. 122-123".…”

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Synthese von Plectranthonen, diterpenoiden Phenanthren‐1,4‐chinonen

Kaliakoudas

Eugster

Rüedi

1990

Helvetica Chimica Acta

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Synthesis of Plectranthons, Diterpenoid Phenanthrene-1,4-dionesThe following phenanthrene-l,4-diones have been synthesized by using the photocyclization of the corresponding highly substituted stilbenes as the key step : 3-hydroxy-5,7,8-trimethyl-2-(prop-2-enyl)phenanthrene-1,4-dione (l), (RS)-, (R )-, and (S)-2-[3-hydroxy-5,7,8-trimethyl-1,4-dioxophenanthren-2-y1]-1 -methylethyl acetate (2, 31, and 32, resp.), 3-hydroxy-7,8-dimethyl-2-(prop-2-enyl)phenanthrene-1,4-dione (3), 3-hydroxy-7,8,10-trimethyl-2-(prop-2-enyl)phenanthrene-I ,4-dione (4), 5,7,8-trimethyl-2-(prop-2-enyl)phenanthrene-1 ,4-dione (17), and 3-hydroxy-2-methylphenanthrene-1,4-dione (42). The quinones 1 and 3 proved to be identical with the recently isolated plectranthons A and C. Compounds 2, 31, and 32 exhibited the same UVjVIS, IR, 'H-NMR and mass spectra as natural plectranthon B, but had different melting points. This might be due either to crystal modifications or to diastereoisomerism caused by the helical structure of the phenanthrene-1.4-dione skeleton. The spectral data of synthetic 4 were not compatible with those of natural plectranthon D for which structure 4 had been proposed based mainly on 'H-NMR arguments concerning the chemical shifts of H-C(9) and H-C(10) in 1-3. Extensive 'H-NMR investigations have now revealed that the currently stated assignments of the H-C(9)/ H-C(1O) AB system have to be reversed for highly substituted phenanthrene-l,4-diones: in the model compounds 2-methylphenanthrene-1.4-dione (41) and 2, H-C( 10) resonates at lower field as expected (peri-position), whereas in the highly substituted congeners 1,2,3,31, and 32, H-C(9) is shifted paramagnetically, a fact which had lead to the erroneous assignment of structure 4 for natural plectranthon D. Um die Gruppe der Plectranthone besser zuganglich zu machen, sie weiter zu charakterisieren sowie die Strukturvorschlage abzusichern, haben wir nun einen allgemein anwendbaren Weg zur Synthese von substituierten Phenanthren-1,4-chinonen ausgearbeitet. Uber die erzielten Ergebnisse wird im folgenden berichtet. Aufgrund von Vorversuchen entschieden wir uns fur den Aufbau via eine photochemische Stilben-Cyclisierung

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Synthese von Plectranthonen, diterpenoiden Phenanthren‐1,4‐chinonen

Kaliakoudas

Eugster

Rüedi

1990

Helvetica Chimica Acta

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“…Published descriptions 2–10 of molecular structures and odor intensities of 203 musk‐related molecules were used in this study. Odor intensities for molecules 1–170 were classified into the following four categories: strong, represented by grade 3; medium, grade 2; weak, grade 1; odorless, grade 0 (Table I).…”

Section: Methodsmentioning

confidence: 99%

“…Odor intensities for molecules 1–170 were classified into the following four categories: strong, represented by grade 3; medium, grade 2; weak, grade 1; odorless, grade 0 (Table I). Odor intensities described as very strong, strong, and fairly strong in the reports 2–10 are included in grade 3. We only obtained data on the presence and absence of musk odor instead of intensity levels, for molecules 171–203 6, 7, 9, 10.…”

Section: Methodsmentioning

confidence: 99%

“…Musk molecules are known to have a wide variety of chemical structures and are the most systematically studied in terms of their odor intensities in perfumery. To find the reactive sites of musk molecules, we investigated electronic localizations of 203 musk‐related molecules including all structural varieties 2–10. The relationship between electronic localizations and odor intensities was studied by discriminative function analysis and multiple regression analysis.…”

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Molecular orbital approach to possible discrimination of musk odor intensity

Ishikawa

Kawakami

2000

Int. J. Quantum Chem.

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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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NITRO MUSKS. III.¹ ASYMMETRICAL MUSKS OF THE DINITRO-tert-BUTYL-m-XYLENE SERIES

Cited by 16 publications

References 8 publications

Synthese von Plectranthonen, diterpenoiden Phenanthren‐1,4‐chinonen

Synthese von Plectranthonen, diterpenoiden Phenanthren‐1,4‐chinonen

Molecular orbital approach to possible discrimination of musk odor intensity

A Chemical History of Polycyclic Musks

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NITRO MUSKS. III.1 ASYMMETRICAL MUSKS OF THE DINITRO-tert-BUTYL-m-XYLENE SERIES

Cited by 16 publications

References 8 publications

Synthese von Plectranthonen, diterpenoiden Phenanthren‐1,4‐chinonen

Synthese von Plectranthonen, diterpenoiden Phenanthren‐1,4‐chinonen

Molecular orbital approach to possible discrimination of musk odor intensity

A Chemical History of Polycyclic Musks

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Product

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NITRO MUSKS. III.¹ ASYMMETRICAL MUSKS OF THE DINITRO-tert-BUTYL-m-XYLENE SERIES