WO1996020185A3 - Tetrahydrofurans and tetrahydropyrans - Google Patents

Tetrahydrofurans and tetrahydropyrans Download PDF

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Publication number
WO1996020185A3
WO1996020185A3 PCT/EP1995/005002 EP9505002W WO9620185A3 WO 1996020185 A3 WO1996020185 A3 WO 1996020185A3 EP 9505002 W EP9505002 W EP 9505002W WO 9620185 A3 WO9620185 A3 WO 9620185A3
Authority
WO
WIPO (PCT)
Prior art keywords
tetrahydrofurans
carbon atoms
alkyl group
methyl groups
higher alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP1995/005002
Other languages
French (fr)
Other versions
WO1996020185A2 (en
Inventor
Paul David Noire
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Givaudan SA
Original Assignee
Givaudan Roure International SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Givaudan Roure International SA filed Critical Givaudan Roure International SA
Priority to EP95942177A priority Critical patent/EP0746552B1/en
Priority to DE69527045T priority patent/DE69527045T2/en
Priority to JP8520178A priority patent/JPH11505511A/en
Publication of WO1996020185A2 publication Critical patent/WO1996020185A2/en
Publication of WO1996020185A3 publication Critical patent/WO1996020185A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/06—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • 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)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyrane Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

Novel odorants or odorant compositions which are characterized by a content of one or more compounds selected from the group consisting of tetrahydrofurans of structures (I) or tetrahydropyrans of structure (I'), wherein R can be an aliphatic chain, namely a chain of at least four carbon atoms substituted with at least three methyl groups in the chain, a monocarbocyclic residue, where monocarbocyclic refers to one ring of 5-8 carbon atoms, and with at least two methyl groups, e.g. on the ring, or the residue of a bicyclic ring system, where bicyclic refers to two carbon rings, having between 5-8 carbon atoms, fused together, the bicyclic system substituted with at least two methyl groups, or R + R3 can also form a spirocyclic moiety in case of the tetrahydrofurans, and wherein R1 = H or CH¿3?, or a higher alkyl group, R?2¿ = H, CH¿3?, or a higher alkyl group, R?3¿ = H, or CH¿3?, R?4 and R5¿ = H, CH¿3?, or a higher alkyl group, and wherein R?1 = R2¿ ¸ H.
PCT/EP1995/005002 1994-12-23 1995-12-18 Tetrahydrofurans and tetrahydropyrans Ceased WO1996020185A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP95942177A EP0746552B1 (en) 1994-12-23 1995-12-18 Tetrahydrofurans and tetrahydropyrans
DE69527045T DE69527045T2 (en) 1994-12-23 1995-12-18 TETRAHYDROFURANE AND TETRAHYDROPYRANE
JP8520178A JPH11505511A (en) 1994-12-23 1995-12-18 Tetrahydrofuran and tetrahydropyran

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/363,685 US5510326A (en) 1994-12-23 1994-12-23 Multi-substituted tetrahydrofurans
US08/363,685 1994-12-23

Publications (2)

Publication Number Publication Date
WO1996020185A2 WO1996020185A2 (en) 1996-07-04
WO1996020185A3 true WO1996020185A3 (en) 1996-09-06

Family

ID=23431263

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/005002 Ceased WO1996020185A2 (en) 1994-12-23 1995-12-18 Tetrahydrofurans and tetrahydropyrans

Country Status (6)

Country Link
US (2) US5510326A (en)
EP (1) EP0746552B1 (en)
JP (1) JPH11505511A (en)
DE (1) DE69527045T2 (en)
ES (1) ES2176353T3 (en)
WO (1) WO1996020185A2 (en)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6617490B1 (en) * 1999-10-14 2003-09-09 Kimberly-Clark Worldwide, Inc. Absorbent articles with molded cellulosic webs
DE10304832A1 (en) * 2003-01-31 2004-08-26 Schefenacker Vision Systems Germany Gmbh & Co. Kg Light, in particular rear light for motor vehicles, and carriers, preferably for such a light
FR2873922B1 (en) * 2004-08-06 2008-10-17 Mane Fils Sa V BETA-SUBSTITUTED TETRAHYDROPYRAN (ON), PROCESS FOR THEIR SYNTHESIS AND THEIR USE IN PERFUMERY
KR100614546B1 (en) 2004-09-13 2006-08-25 한국과학기술연구원 Tetrahydrofuran cyclic compounds having high stereoselectivity and preparation method thereof
ATE539045T1 (en) * 2005-07-01 2012-01-15 Firmenich & Cie WOODY TYPE PERFUME INGREDIENTS
JP5489721B2 (en) * 2006-12-01 2014-05-14 ヴィ・マン・フィス Methods of preparing and using pyran derivatives, fragrances and flavorings
US7875737B2 (en) 2006-12-01 2011-01-25 V. Mane Fils Pyran derivatives, process of preparation and use thereof in perfumery and flavouring
EP1927593A1 (en) * 2006-12-01 2008-06-04 V. Mane Fils Pyran derivates, process of preparation and use thereof in perfumery and flavouring
EP2047758A1 (en) * 2007-10-09 2009-04-15 V. Mane Fils Bicyclic campholenic derivatives
US9115331B2 (en) * 2013-05-07 2015-08-25 International Flavors & Fragrances Inc. 3,3-diethyl-alkyl-2-oxa-spiro[4.5]dec-7-enes and their use in perfume compositions
CN104262319B (en) * 2014-08-14 2016-08-24 江西农业大学 Aldehyde cyclic acetal compounds and synthetic method thereof are foretold in a kind of hydrogenation promise
JP2020002316A (en) * 2018-06-29 2020-01-09 恭隆 吉田 Ambergris fluorescent substance and method for producing the same, fluorescent material, and method for discriminating ambergris
WO2024045134A1 (en) * 2022-09-01 2024-03-07 Givaudan Sa Organic compounds
WO2025111825A1 (en) * 2023-11-29 2025-06-05 Givaudan Sa Organic compounds

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU850653A1 (en) * 1979-08-17 1981-07-30 Калужский Филиал Всесоюзного Научно- Исследовательского Института Синтети-Ческих И Натуральных Душистых Веществ Perfume composition
EP0049543A1 (en) * 1980-10-06 1982-04-14 Naarden International N.V. Perfume compositions and perfumed materials and articles, containing phenyl-tetrahydrofurans as a fragrance
CH685390A5 (en) * 1993-02-16 1995-06-30 Firmenich & Cie New poly:alkyl-tetra:hydro-furan derivs

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3463818A (en) * 1966-01-25 1969-08-26 Int Flavors & Fragrances Inc Unsaturated aldehydes and alcohols
US3417107A (en) * 1966-08-17 1968-12-17 Norda Essential Oil And Chemic Naphthospirofuran compound
US4549029A (en) * 1983-04-05 1985-10-22 Givaudan Corporation Substituted tetrahydrofurans
SU1169971A1 (en) * 1983-12-08 1985-07-30 Ордена Трудового Красного Знамени Институт Химии Ан Мсср 2-methyl-3-(1s,2s)-13,3-trimethyl-2-ethblcyclohexyl-tetrahydrofuran as fragrant component in perfume composition
EP0266648B1 (en) * 1986-11-03 1993-01-20 Roure S.A. Polysubstituted norcaranes
GB8701961D0 (en) * 1987-01-29 1987-03-04 Unilever Plc Perfumery materials

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU850653A1 (en) * 1979-08-17 1981-07-30 Калужский Филиал Всесоюзного Научно- Исследовательского Института Синтети-Ческих И Натуральных Душистых Веществ Perfume composition
EP0049543A1 (en) * 1980-10-06 1982-04-14 Naarden International N.V. Perfume compositions and perfumed materials and articles, containing phenyl-tetrahydrofurans as a fragrance
CH685390A5 (en) * 1993-02-16 1995-06-30 Firmenich & Cie New poly:alkyl-tetra:hydro-furan derivs

Non-Patent Citations (19)

* Cited by examiner, † Cited by third party
Title
A. SRIKRISHNA ET AL.: "A New Tetrahydrofurannulation via Tandem Radical Cyclisation Reaction-Reductive Deoxygenation Sequence", TETRAHEDRON LETT., vol. 36, no. 7, 1995, pages 1127 - 1128, XP000565604 *
C. A. BROKA, T. SHEN: "Reductive Lithiation Mediated Anionic Cyclizations and [2,3]-Sigmatropic Rearrangements", J. AM. CHEM. SOC., vol. 111, no. 8, 1989, pages 2981 - 2984, XP000565596 *
C. BROUARD ET AL.: "(2R, 4E)-1,6-Bistrimethylsilylhexa-2,4-diene: Application à la synthèse de 3,4-divinyloxolanes", TETRAHEDRON, vol. 48, no. 12, 1992, pages 2385 - 2400, XP002002297 *
CHEMICAL ABSTRACTS, vol. 107, no. 21, 23 November 1987, Columbus, Ohio, US; abstract no. 198066v, page 738; XP002002298 *
CHEMICAL ABSTRACTS, vol. 77, no. 15, 9 October 1972, Columbus, Ohio, US; abstract no. 101480b, C. HIRAI ET AL.: "Acid-catalyzed reaction of 1-octene and 2-octene with formaldehyde" page 419; XP002002299 *
I. N. NAZAROV ET AL.: "Synthesis and transformations of 3-vinylethinyltetrahydro-3-furanols", ZH. OBSBSHCHEI KHIM., vol. 27, 1957, pages 2951 - 2961, XP002002289 *
J. KULA, M. SIKORA: "Studies on the Synthesis of Tetrahydrofuran and Tetrahydropyran Derivatives from Terpenes. Part V [1]. Transformation of cis-2-[3-(1-Hydroxy-1-methylethyl)-2,2-dimethylcyclobutyl]ethanol and cis-2-[3-(2-Hydroxy-2-methylpropyl)-2,2-dimethylcyclopropyl]ethanol into Tetrahydrofuran Derivatives", POL. J. CHEM., vol. 68, no. 9, 1994, pages 1699 - 1706, XP002002287 *
J. KULA: "Studies on the synthesis of tetrahydrofuran and tetrahydropyran derivatives from cyclic terpene hydrocarbons. Part II. Transformation of cis-substituted 2,2-dimethylcyclopropaneethanols into tetrahydrofuran and tetrahydropyran derivatives", POL. J. CHEM., vol. 65, no. 2-3, 1991, pages 333 - 344, XP002002296 *
L. D. WESCOTT, JR. ET AL.: "Molecular Structure and Polymerization Mechanism of Poly(vinylchloride-co-carbon monoxide)", MACROMOLECULES, vol. 17, no. 12, 1984, pages 2501 - 2507, XP000565608 *
M. HUHTASAARI ET AL.: "Anodic oxidation. Part 32. Cyclization of 3-allyloxycarboxylic acids to tetrahydrofurans by Kolbe's electrolysis", ANGEW. CHEM., vol. 96, no. 12, 1984, pages 995 - 996, XP002002291 *
N. RABJOHN ET AL.: "The Reaction of 2-(beta-Cyanoethyl)-2-Ethylhexanal with Grignard Reagents", J. ORG. CHEM., vol. 21, 1956, pages 285 - 286, XP000565590 *
P. PICARD ET AL.: "Heterocyclic spiro compounds. V. Synthesis and configurational analysis of 2-oxaspiro[4.5]decanes", BULL. SOC. CHIM. FR., no. 1-2, Pt. 2, 1984, pages 656 - 70, XP002002292 *
S. A. VARTANYAN ET AL.: "Chemistry of Vinylacetylene. LXXVII. Synthesis and reactions of 2,2,5,5-tetramethyl-3-(isopropenylethynyl)-tetrahydro-3-furanol", ARM. KHIM. ZH., vol. 20, no. 6, 1967, pages 438 - 446, XP002002295 *
S. A. VARTANYAN ET AL.: "Vinylacetylene chemistry. LXXIX. Synthesis and conversions of 2,2,5-trimethyl-3-isopropenylethinyltetrahydrofuran-3-ol", ARM. KHIM. ZH., vol. 20, no. 9, 1967, pages 741 - 746, XP002002294 *
T. FUJITA ET AL.: "A Convenient Preparation of gamma-Lactones and Dialkyltetrahydrofurans From the Reaction of Fatty Acids with Epoxides Using Lithium Naphthalenide", J. AM. OIL CHEM. SOC., vol. 61, no. 10, 1984, pages 1604 - 1606, XP000565588 *
V. M. ANDREEV ET AL.: "Preparation of a new perfume substance - pinoran, from by-products of methylheptenone production", MASLO-ZHIR. PROM-ST., no. 3, 1979, pages 36 - 38, XP002002293 *
YU. K. YUR'EV ET AL.: "2,5-Dimethyl-3-furanidone in the synthesis of 2,5-dimethyl-3-alkyl- and 2,5-dimethyl-3-arylfuranidines", ZHUR. OBSHCHEI KHIM., vol. 29, 1959, pages 3867 - 3872, XP002002288 *
YU. K. YUR'EV ET AL.: "Synthesis of 2,3,5-trialkylthiophanes by catalytic transformation of 2,3,4-trialkylfuranidines", KHIM. NAUKA I PROM., vol. 3, 1958, pages 830 - 831, XP002002290 *
YUKAGAKU, vol. 21, no. 7, 1972, pages 359 - 366 *

Also Published As

Publication number Publication date
ES2176353T3 (en) 2002-12-01
WO1996020185A2 (en) 1996-07-04
EP0746552B1 (en) 2002-06-12
JPH11505511A (en) 1999-05-21
US5510326A (en) 1996-04-23
DE69527045D1 (en) 2002-07-18
DE69527045T2 (en) 2002-10-24
US5665696A (en) 1997-09-09
EP0746552A1 (en) 1996-12-11

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