MX2007006396A - Dioxole tricyclic compounds and their use as fragrances - Google Patents
Dioxole tricyclic compounds and their use as fragrancesInfo
- Publication number
- MX2007006396A MX2007006396A MXMX/A/2007/006396A MX2007006396A MX2007006396A MX 2007006396 A MX2007006396 A MX 2007006396A MX 2007006396 A MX2007006396 A MX 2007006396A MX 2007006396 A MX2007006396 A MX 2007006396A
- Authority
- MX
- Mexico
- Prior art keywords
- isopropyl
- ethyl
- methyl
- propyl
- butyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 25
- 239000003205 fragrance Substances 0.000 title claims abstract description 14
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3H-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 title 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 12
- 125000004432 carbon atoms Chemical group C* 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 10
- VLTAGEOKWFDKSE-UHFFFAOYSA-N C1C2C(C)(C)CC1(C(C)C)CC1OC(C)(C)OC12C Chemical compound C1C2C(C)(C)CC1(C(C)C)CC1OC(C)(C)OC12C VLTAGEOKWFDKSE-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 101700067048 CDC13 Proteins 0.000 description 5
- RSJKGSCJYJTIGS-UHFFFAOYSA-N Undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YUUHJYBQNSYHLF-UHFFFAOYSA-N 2,7,7-trimethyl-5-propan-2-ylbicyclo[3.2.1]oct-2-ene Chemical compound C1C2C(C)=CCC1(C(C)C)CC2(C)C YUUHJYBQNSYHLF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000008079 hexane Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N t-BuOH Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-Dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
- IOEICAHMUSBJBU-UHFFFAOYSA-N 7,7-dimethyl-5-propan-2-ylbicyclo[3.2.1]octan-2-ol Chemical compound C1C2C(O)CCC1(C(C)C)CC2(C)C IOEICAHMUSBJBU-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N MeOtBu Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N P-Toluenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000003197 catalytic Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 235000019645 odor Nutrition 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
A compound of the formula (I) in which the moieties R1-R13are independently selected from the following moieties:R1, R5, R6, R8, R11- H, methyl, ethyl, propyl, isopropyl;R3- H, methyl, ethyl, propyl, isopropyl, vinyl;R4- H, methyl, ethyl;R2, R7, R9- H, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl;R10- H, methyl, ethyl, propyl, isopropyl, t-butyl;R12, R13- H, C1-6linear or branched alkyl;or R4and R11together with the carbon atoms to which they are attached form a 5- or a 6-membered cycloalkyl ring;or R6and R7together with the carbon atoms to which they are attached form a cycloalkyl ring having 3, 4, 5 or 6 members. The compounds have strong odours and are useful in fragrances and fragrance applications.
Description
COMPOUNDS
DESCRIPTION OF THE INVENTION The invention relates to chemical compounds, and more particularly to chemical compounds having improved fragrance properties, and to compositions including such compounds. It has been found that certain di oxa-t ri c i c o -undecano compounds have desirable olfactory properties and therefore can be used in applications where such properties are desirable. The invention therefore provides a compound of formula I.
wherein the R ^ R13 fractions are independently selected from the following fractions: R1, R5, R6, R8, R11-H, methyl, ethyl, propyl, isopropyl; R3-H, methyl, ethyl, propyl, isopropyl, vinyl; REF S182355
R 4 - H, methyl, ethyl; R2, R7, R9-H, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl; R 10 -H, methyl, ethyl, propyl, isopropyl, t-bu t i 1 o; R12, R13-H, Ci- 6 linear or branched alkyl; or R4 and R11 together with the carbon atoms to which they are attached form a 5 or 6 membered cycloalkyl ring; or R6 and R7 together with the carbon atoms to which they are attached form a cycloalkyl ring having 3, 4, 5 or 6 members. The definition given above encompasses all stereochemical forms of the compound. The compound described above can be a mixture of isomers, or, if desired, this can be resolved by the known methods in individual isomers. However, as such resolution inevitably adds cost of the process and therefore of the final materials, it is preferred to use the compound as a mixture. A preferred compound is 8-isopropyl-2,4,4,10,10-pentamethi-3, 5-dioxa-tricyclo [6.2.1.02,6] undecane. The compounds of the invention can be prepared by known methods, starting from the
known compounds
In which the fractions R1-! 10 have the meanings defined above. The compounds of the invention have strong odors of trees and nouns and are useful in the preparation of fragrances and fragrance compositions. The invention therefore provides the use as a fragrance of a compound as defined above. The invention further provides the use in a fragrance composition of a compound as defined above. The compounds can be used in a wide range of fragrance applications, such as fine and functional fragrances, including perfumes, cosmetics, body care products and household products, for example, laundry, dish washing and washing products, brighteners and cleaners, etc. The invention therefore also provides a fragrance application comprising at least one compound as defined above. The invention is further described with reference to
The following non-limiting examples before. Example 1 5- Isopropyl-2,7,7-trimethyl-bicyclo [3.2.1] oct-2-ene
A solution of 5-isopropyl-7,7-dimethyl-bicyclo [3.2.1] octan-2-ol (18.5 g, 88 mmol) and KHS0 (100 mg) in toluene (250 mL) was heated 36 h in a Dean apparatus. Stark The solution was cooled and washed once with water and brine, dried (MgSO 4) and concentrated in vacuo to yield 5-isopropyl-2,7,7-trimethyl-bicyclo [3.2.1] oct-2-ene (13.77 g, 81%). 13H_ MR (100 MHz, CDCI3): 140.4 (s), 118.7 (d), 52.1 (d), 51.5 (t), 46.1 (s), 46.0 (s), 39.1 (t), 37.6 (d), 37.4 (t), 31.5 (q), 26.9 (q), 24.6 (q), 18.2 (q), 18.0 (q) ppm. GC / MS (El): 192 (M +, 17), 177 (4), 149 (22), 136 (21), 121 (15), 107 (18), 93 (100), 77 (28), 57 (17), 41 (23). IR (ATR): 2957s, 2933s, 2869m, 1468m, 1452m, 1366m cm "1 .8-Isopropyl-2 4, 4, 10, 10-pentamethyl-3,5-dioxa-tricyclo [6.2.1 .O2'6 ] undecano A solution of 5-isopropyl-2,7,7-trimethyl-bicyclo [3.2.1] oct-2-ene (1.00 g, 5.2 mmol), Os04 (0.052 mmol, 2.5% in t-BuOH) and N -morpholine-N-oxide (913.3 mg, 6.76 mmol) in aqueous acetone (10 ml) was stirred at room temperature for 40 h.The mixture was diluted with MTBE, filtered, concentrated in vacuo and the residue was purified by chromatography on silica ( hexane: ethyl acetate = 7: 3). To the resulting diol (0.4g) were added 2, 2-dimethoxy-propane (5 ml) and one
catalytic amount of p-TsOH and the solution was stirred for 5 h at room temperature. The mixture was concentrated and the residue purified by chromatography over silica (hexane: ethyl acetate = 95: 5) to yield an uncolored oil (0.41 g, 30%). 1 H-NMR (400 MHz, CDC13): 4.12 (dd, J = 8.9 Hz, 8.5Hz, 1H, 6-H), 2.09 (dd, J = 12.0 Hz, 2.1 Hz, 1H, 11-Ha), 1.84 ( d, J = 5.1 Hz, 1H, 1-H), 1.80 (ddd, J = 14.2 Hz, 8.9 Hz, 2.5 Hz, 1H, 7-Ha), 1.62 (ddd, J = 14.2 Hz, 6.1 Hz, 2.1 Hz , 1H, 7-Hb), 1.53-1.48 (m, 1H, ll-Hb), 1.52 (s, 3H), 1.48 (s, 6H), 1.46 (sept., J = 6.8 Hz, 1H, S-CH (CH3) 2), 1-38 (dd, J = 13.2 Hz, 2.0 Hz, 1H, 9-Ha), 1.26 (dd, J = 13.2 Hz, 2.0 Hz, 1H, 9-Hb), 1.16 (s, 3H), 1.10 (s, 3H), 0.86 (d, J = 6.8 Hz, 3H, 8-CH (CH3) a), 0.80 (d, J = 6.8 Hz, 3H, 8-CH (CH3) b) ppm . 13H_ MR (100 MHz, CDC13): 108.6 (s), 84.6 (s), 78.2 (d), 54.3 (d), 52.4 (t), 45.7 (s), 39.4 (s), 38.1 (t), 37.7 (d), 36.1 (t), 35.1 (q), 30.4 (q), 29.7 (q), 29.4 (q), 27.6 (q), 18.2 (q), 17.9 (q) ppm. GC / MS (El): 266 (M +, l) 251 (14), 209 (46), 165 (98), 137 (67), 109 (31), 95 (52), 81 (42), 69 ( 36), 55 (39), 43 (100), 41 (49). IR (ATR): 2958m, 2873m, 1466m, 1366m, 1229s, 1207m, 1074s, 1049m, 1014m cm "1. Example 2 The following compounds were prepared according to example 1. 5-sec-Butyl-2 # 7, 7-trimethyl-bicyclo [3.2.1] oct-2-ene Mixture of 2 diastereomers: 13H_NMR (100 MHz, CDC13): 140.4
(2s), 118.7, 118.6 (d), 52.7, 52.3 (t), 52.0, 51.9 (d), 46.7, 46.6 (s), 45.9, 45.8 (s), 45.8, 45.5 (d), 39.5, 39.3 ( t), 37.6, 37.0 (t), 31.6, 31.5 (q), 26.9 (2q), 24.9, 24.8 (t), 24.6 (2q), 14.2, 14.1 (q), 18.0, 12.9 (q) ppm . GC / MS (EI): 206 (M +, 14), 177 (4), 149 (38), 135 (4), 121 (24), 107 (19), 93 (100), 77 (18), 57 (35), 41 (17). IR (ATR): 2959s, 2930s, 2866m, 1451m, 1378m, 884m cm "" 1. 8-sec-Butyl-2, 4, 4, 10-10-pentamethyl-3,5-dioxa-tricyclo [6.2.1.02'6] undecane Mixture of 2 diastereomers (in a proportion of
1: 1): 1H-MR (400 MHz, CDC13): 4.10 (ddd, J = 2.5.6.2.8.7 Hz, 1H), 2.18-2.11 (m, 1H), 1.85-1.81 (m, 1H), 1.79 -1.26 (m, 6H), 1.52 (s, 3H), 1.48 (s, 6H), 1.15 (s, 3H), 1.10 (s, 3H), 0.88 (t, J = 7.4Hz, 3H), 0.85, 0.78 (2d, J = 6.8 Hz, 3H) ppm. 13H_ MR (100 MHz, CDC13): 108.6 (2s), 84.6 (2s), 78.2 (2s), 54.2, 54.1 (d), 53.3, 53.1 (t), 46.2 (2s), 45.9 (d), 45.6 ( d), 39.4, 39.2 (s), 38.3, 38.1 (t), 36.4, 36.2 (t), 35.1 (2q), 30.4 (2q), 29.7 (2q), 29.4 (2q), 27.6 (2q), 24.9 , 24.8 (t), 14.3, 14.0 (q), 13.0, 12.8 (q) ppm. GC / MS (El): 280 (M +, 2), 265 (35), 223 (96), 165 (31), 151 (100), 109 (24), 95 (33), 81 (18), 57 (33), 43 (35). It is noted that in relation to this date the best method known by the applicant to carry out the present invention is that which is clear from the present description of the invention.
Claims (1)
1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0426376.0 | 2004-12-02 | ||
| GB0507925.6 | 2005-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2007006396A true MX2007006396A (en) | 2008-10-03 |
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