Synthetic approaches to the damascone and damascenone isomers

A comprehensive review on multi-colored emissive carbon dots as fluorescent probes for the detection of pharmaceutical drugs in water

“…132 Riboflavin, also called vitamin B 2 , is used for skin growth, blood cells, and brain function; it prevents migraines and maintains the levels of homocysteine in the blood. 133 A ratiometric C-dot fluorescence sensor has been developed by Du et al for the detection of vitamin B 2 . 134 The fluorescence of C-dots underwent a shift from blue to greenish yellow, and the maximum emission wavelength of the C-dots at 470 nm decreased and a new peak at 532 nm was observed with an increase in vitamin B 2 concentration (Fig.…”

Synthesis of β-damascone from 2,6-dimethylcyclohexanone

“…4, 146.0, 140.3, 134.8, 130.6, 38.9, 33.5, 31.3, 29.0 (2C), 21.4, 19.0, 18.5. MS (EI) m/z: 192 (M + , 39), 178 (13), 177 (100), 159 (8), 149 (13), 135 (18), 123 (48), 121 (32), 109 (13), 107 (39), 105 (9), 95 (17), 93 (19), 91 (17), 81 (50), 79 (19), 77 (14), 69 (75), 67 (16), 65 (8), 57 (8), 55 (19), 53 (11).…”

“…1 H NMR (400 MHz, CDCl3): δ 4.97 (br s, 2H), 3.03-2.95 (m, 1H), 1.85-1.73 (m, 1H), 1.67-1.54 (m, 3H), 1.51-1.39 (m, 2H), 1.17 (d, J 7.5 Hz, 3H), 1.13 (s, 3H), 1.12 (s, 3H). 13 (17), 137 (15), 136 (10), 126 (15), 125 (8), 124 (9), 123 (41), 122 (61), 112 (24), 111 (28), 110 (10), 109 (34), 108 (14), 107 (14), 105 (9), 99 (16), 98 (10), 97 (27), 96 (24), 95 (39), 94 (28), 93 (11), 86 (20), 85 (40), 84 (13), 83 (30), 82 (23), 81 (67), 80 (15), 79 (16), 77 (8), 72 (51), 71 (10), 70 (38), 69 (53), 68 (38), 67 (46), 65 (7), 58 (32), 57 (24), 56 (42), 55 (94), 54 (17), 53 (23). 2-Iodo-1,3,3-trimethylcyclohex-1-ene (7).…”

“…13 C NMR (101 MHz, CDCl3): δ 175.8, 136.6, 133.9, 38.5, 33.0, 31.6, 28.3 (2C), 21.6, 18.6. MS (EI) m/z: 168 (M + , 18), 154 (9), 153 (100), 135 (37), 126 (10), 125 (20), 123 (44), 109 (11), 108 (6), 107 (66), 105 (7), 95 (6), 93 (9), 91 (23), 81 (25), 79 (27), 77 (15), 68 (6), 67 (22), 65 (9), 59 (6), 57 (4), 55 (16), 53 (12), 51 (6).…”

“…A number of strategies involving different starting materials have been reported to synthesize βdamascone, such as β-ionone, β-cyclocitral (synthetized from citral), β-cyclogeranate as well as cyclohexanone and their derivatives. 16 Among the methods developed to synthesize β-damascone, different rearrangements were used such as a Wharton, 17,18 a Büchi-Vederas, 19,20 an Overman 21 rearrangement or epoxide rearrangements, 22 as well as a Rupe rearrangement which consist of the rearrangement of a propargylic alcohol to an β-unsaturated enone. 23,24 In 1981, it was reported that by using a Rupe rearrangement, 25 βdamascone could be prepared in six steps from 2,6,6-trimethylcyclohex-2-en-1-one, which was prepared by a Diels-Alder reaction.…”