RU2562973C2 - Новые бициклические диоксаны, их получение и применение в качестве ароматических соединений - Google Patents
Новые бициклические диоксаны, их получение и применение в качестве ароматических соединений Download PDFInfo
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- RU2562973C2 RU2562973C2 RU2012107548/04A RU2012107548A RU2562973C2 RU 2562973 C2 RU2562973 C2 RU 2562973C2 RU 2012107548/04 A RU2012107548/04 A RU 2012107548/04A RU 2012107548 A RU2012107548 A RU 2012107548A RU 2562973 C2 RU2562973 C2 RU 2562973C2
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- Prior art keywords
- dioxin
- group
- methyl
- ethyl
- cdcl
- Prior art date
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- -1 bicyclic dioxanes Chemical class 0.000 title claims abstract description 29
- 150000001491 aromatic compounds Chemical class 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 90
- 239000000203 mixture Substances 0.000 claims abstract description 69
- 125000003118 aryl group Chemical group 0.000 claims abstract description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 18
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 17
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 14
- 239000000126 substance Substances 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000002304 perfume Substances 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 230000000873 masking effect Effects 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 239000012141 concentrate Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 60
- 238000005160 1H NMR spectroscopy Methods 0.000 description 57
- 238000002360 preparation method Methods 0.000 description 45
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- 235000019198 oils Nutrition 0.000 description 37
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
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- 150000002009 diols Chemical class 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- MNBLGXDUGKWAQZ-UHFFFAOYSA-N 2-benzyl-4-methyl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound O1C2CCCCC2C(C)OC1CC1=CC=CC=C1 MNBLGXDUGKWAQZ-UHFFFAOYSA-N 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 18
- 239000012230 colorless oil Substances 0.000 description 18
- GUTOMDCBWXPRJO-UHFFFAOYSA-N 2-ethyl-4-methyl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound C1CCCC2OC(CC)OC(C)C21 GUTOMDCBWXPRJO-UHFFFAOYSA-N 0.000 description 14
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 125000005594 diketone group Chemical group 0.000 description 13
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 13
- IIQFBBQJYPGOHJ-UHFFFAOYSA-N 4-(cyclohexen-1-yl)morpholine Chemical compound C1CCCC(N2CCOCC2)=C1 IIQFBBQJYPGOHJ-UHFFFAOYSA-N 0.000 description 12
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- 238000000034 method Methods 0.000 description 9
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
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- 239000002904 solvent Substances 0.000 description 7
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 6
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 6
- 229940126062 Compound A Drugs 0.000 description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 6
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 239000002537 cosmetic Substances 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 239000006210 lotion Substances 0.000 description 6
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 description 6
- 240000007185 Albizia julibrissin Species 0.000 description 5
- 235000011468 Albizia julibrissin Nutrition 0.000 description 5
- 150000001241 acetals Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 239000002781 deodorant agent Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
- CBAWGSXVHCATED-UHFFFAOYSA-N 2-(1-hydroxy-3-methylbutyl)cyclohexan-1-ol Chemical compound CC(C)CC(O)C1CCCCC1O CBAWGSXVHCATED-UHFFFAOYSA-N 0.000 description 4
- IRORBXUOUURXRE-UHFFFAOYSA-N 2-(1-hydroxypropyl)cyclohexan-1-ol Chemical compound CCC(O)C1CCCCC1O IRORBXUOUURXRE-UHFFFAOYSA-N 0.000 description 4
- XXDOKDGDIMZUJO-UHFFFAOYSA-N 2-(3-methylbutanoyl)cyclohexan-1-one Chemical compound CC(C)CC(=O)C1CCCCC1=O XXDOKDGDIMZUJO-UHFFFAOYSA-N 0.000 description 4
- CJBGXBKIDRIJOB-UHFFFAOYSA-N 2-[hydroxy(phenyl)methyl]cyclohexan-1-ol Chemical compound C=1C=CC=CC=1C(O)C1CCCCC1O CJBGXBKIDRIJOB-UHFFFAOYSA-N 0.000 description 4
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- 229940089454 lauryl aldehyde Drugs 0.000 description 1
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 description 1
- HRGPYCVTDOECMG-RHBQXOTJSA-N methyl cedryl ether Chemical compound C1[C@@]23[C@H](C)CC[C@H]2C(C)(C)[C@]1([H])[C@@](OC)(C)CC3 HRGPYCVTDOECMG-RHBQXOTJSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- FLKPEMZONWLCSK-UHFFFAOYSA-N phthalic acid di-n-ethyl ester Natural products CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 230000008786 sensory perception of smell Effects 0.000 description 1
- KWVISVAMQJWJSZ-VKROHFNGSA-N solasodine Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CN1 KWVISVAMQJWJSZ-VKROHFNGSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- NPFVOOAXDOBMCE-UHFFFAOYSA-N trans-3-hexenyl acetate Natural products CCC=CCCOC(C)=O NPFVOOAXDOBMCE-UHFFFAOYSA-N 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/008—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing six atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09305713.1 | 2009-07-29 | ||
| EP09305713A EP2287159A1 (en) | 2009-07-29 | 2009-07-29 | New bicyclic dioxanes, their preparation and their use as organoleptic compounds |
| PCT/IB2010/053424 WO2011013077A1 (en) | 2009-07-29 | 2010-07-28 | New bicyclic dioxanes, their preparation and their use as fragrant compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2012107548A RU2012107548A (ru) | 2013-09-10 |
| RU2562973C2 true RU2562973C2 (ru) | 2015-09-10 |
Family
ID=41350300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012107548/04A RU2562973C2 (ru) | 2009-07-29 | 2010-07-28 | Новые бициклические диоксаны, их получение и применение в качестве ароматических соединений |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8569518B2 (https=) |
| EP (2) | EP2287159A1 (https=) |
| JP (1) | JP5717740B2 (https=) |
| CN (1) | CN102482253B (https=) |
| BR (1) | BR112012008069B1 (https=) |
| DK (1) | DK2459546T3 (https=) |
| ES (1) | ES2451521T3 (https=) |
| MX (1) | MX2012001273A (https=) |
| PL (1) | PL2459546T3 (https=) |
| PT (1) | PT2459546E (https=) |
| RU (1) | RU2562973C2 (https=) |
| WO (1) | WO2011013077A1 (https=) |
| ZA (1) | ZA201200562B (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6713474B2 (ja) * | 2015-01-21 | 2020-06-24 | フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ | 活性揮発性カルボニル化合物の制御放出のための光解離性アセタールおよびケタール化合物 |
| CN105044261B (zh) * | 2015-07-02 | 2020-10-16 | 谱尼测试集团深圳有限公司 | 一种个人护理品中卡拉花醛的检测方法 |
| CN115340449B (zh) * | 2022-09-02 | 2024-07-26 | 常州佳德医药科技有限公司 | 一锅法制备2-乙酰基环戊酮的方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU99115102A (ru) * | 1996-12-10 | 2001-05-20 | Бристол-Маерс Сквибб Компани | Мелатонергические агенты - производные бензодиоксола, бензофураан, дигидробензофурана и бензодиоксана |
| US6303798B1 (en) * | 2001-02-23 | 2001-10-16 | International Flavors & Fragrances Inc. | Methylene dioxy tetrahydroindane derivative |
| DE10225350A1 (de) * | 2002-06-07 | 2003-12-18 | Symrise Gmbh & Co Kg | Aromakompositionen mit Frischewirkung |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2935749A1 (de) * | 1979-09-05 | 1981-03-26 | Henkel KGaA, 40589 Düsseldorf | 4-methyl-2,5-dioxa-bicyclo (4.4.0) decan-3-on, dessen herstellung und verwendung als riechstoff sowie dieses enthaltende riechstoffkompositionen |
| PT1027043E (pt) * | 1996-12-10 | 2005-02-28 | Bristol Myers Squibb Co | Benzodioxole benzofurano di-hidrobenzofurano e benzodioxano como agentes melatonergicos |
-
2009
- 2009-07-29 EP EP09305713A patent/EP2287159A1/en not_active Withdrawn
-
2010
- 2010-07-28 CN CN201080038412.4A patent/CN102482253B/zh active Active
- 2010-07-28 WO PCT/IB2010/053424 patent/WO2011013077A1/en not_active Ceased
- 2010-07-28 ES ES10745409.2T patent/ES2451521T3/es active Active
- 2010-07-28 PL PL10745409T patent/PL2459546T3/pl unknown
- 2010-07-28 PT PT107454092T patent/PT2459546E/pt unknown
- 2010-07-28 US US13/387,214 patent/US8569518B2/en active Active
- 2010-07-28 EP EP10745409.2A patent/EP2459546B1/en active Active
- 2010-07-28 BR BR112012008069-5A patent/BR112012008069B1/pt active IP Right Grant
- 2010-07-28 JP JP2012522325A patent/JP5717740B2/ja active Active
- 2010-07-28 RU RU2012107548/04A patent/RU2562973C2/ru active
- 2010-07-28 DK DK10745409.2T patent/DK2459546T3/en active
- 2010-07-28 MX MX2012001273A patent/MX2012001273A/es active IP Right Grant
-
2012
- 2012-01-24 ZA ZA2012/00562A patent/ZA201200562B/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU99115102A (ru) * | 1996-12-10 | 2001-05-20 | Бристол-Маерс Сквибб Компани | Мелатонергические агенты - производные бензодиоксола, бензофураан, дигидробензофурана и бензодиоксана |
| US6303798B1 (en) * | 2001-02-23 | 2001-10-16 | International Flavors & Fragrances Inc. | Methylene dioxy tetrahydroindane derivative |
| DE10225350A1 (de) * | 2002-06-07 | 2003-12-18 | Symrise Gmbh & Co Kg | Aromakompositionen mit Frischewirkung |
Non-Patent Citations (1)
| Title |
|---|
| D.H.Brown et al, Tetrahedron Letters,1986 v.27,p.4367-4370 (соедн.16 стр.4369). M.P.Sibi et al, Angewante Chemie, 2007,p.1-130 (cтр.12 соед.6). * |
Also Published As
| Publication number | Publication date |
|---|---|
| PT2459546E (pt) | 2014-03-20 |
| US8569518B2 (en) | 2013-10-29 |
| ZA201200562B (en) | 2012-10-31 |
| ES2451521T3 (es) | 2014-03-27 |
| PL2459546T3 (pl) | 2014-05-30 |
| JP5717740B2 (ja) | 2015-05-13 |
| BR112012008069B1 (pt) | 2020-12-01 |
| RU2012107548A (ru) | 2013-09-10 |
| DK2459546T3 (en) | 2014-03-24 |
| JP2013500327A (ja) | 2013-01-07 |
| EP2459546A1 (en) | 2012-06-06 |
| CN102482253A (zh) | 2012-05-30 |
| WO2011013077A1 (en) | 2011-02-03 |
| US20120165557A1 (en) | 2012-06-28 |
| BR112012008069A2 (pt) | 2016-03-01 |
| EP2287159A1 (en) | 2011-02-23 |
| MX2012001273A (es) | 2012-06-19 |
| EP2459546B1 (en) | 2013-12-18 |
| CN102482253B (zh) | 2014-08-06 |
| HK1169986A1 (en) | 2013-02-15 |
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