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WO2006125529A1 - Formyltetrahydropyranes, leurs procedes de production et leur utilisation - Google Patents

Formyltetrahydropyranes, leurs procedes de production et leur utilisation Download PDF

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Publication number
WO2006125529A1
WO2006125529A1 PCT/EP2006/004424 EP2006004424W WO2006125529A1 WO 2006125529 A1 WO2006125529 A1 WO 2006125529A1 EP 2006004424 W EP2006004424 W EP 2006004424W WO 2006125529 A1 WO2006125529 A1 WO 2006125529A1
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WIPO (PCT)
Prior art keywords
formula
compounds
independently
formulas
ocf
Prior art date
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PCT/EP2006/004424
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German (de)
English (en)
Inventor
Eike Poetsch
Volker Meyer
Werner Binder
Lars Lietzau
Kai Jaehrling
Kasimir Burek
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Merck Patent GmbH
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Merck Patent GmbH
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.)
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Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Priority to CN2006800180648A priority Critical patent/CN101180285B/zh
Priority to KR1020077030222A priority patent/KR101307585B1/ko
Priority to JP2008512722A priority patent/JP5366541B2/ja
Priority to DE112006000999T priority patent/DE112006000999A5/de
Publication of WO2006125529A1 publication Critical patent/WO2006125529A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-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
    • C07D309/04—Heterocyclic compounds containing six-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, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D309/06—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/18—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member containing only hydrogen and carbon atoms in addition to the ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/20—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hydrogen atoms and substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D309/22—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
    • C09K2019/3408—Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
    • C09K2019/3425—Six-membered ring with oxygen(s) in fused, bridged or spiro ring systems

Definitions

  • Cyclohexane rings within a rod-shaped structure If these cyclohexane rings are replaced by arbitrarily oriented 2,5-substituted tetrahydropyran units, then, depending on the orientation of the
  • DE 3306960 A1 discloses considerations that aldehydes can be prepared by oxidation from alcohols or by reduction from carboxylic acids, but does not disclose any embodiments.
  • 2H-pyrans are also described without reference to liquid crystals.
  • Z ⁇ Z 2 , Z 3 is a single bond, an unsubstituted or mono- or polysubstituted with F and / or Cl alkylene bridge having 1 to 6 carbon atoms, -CH 2 O-, -OCH 2 -, - (CO) O-, -0 (CO) -, -CF 2 O-, -OCF 2 -, -CH 2 CH 2 CF 2 O- or -OCF 2 CH 2 CH 2 -, n is 0, 1, 2, 3 or 4; n2 and n3 are independently 0, 1, 2 or 3; n4 is O, 1 or 2; W 1 is -CH 2 -, -CF 2 - or -O-, R 1 is H, halogen, CN, NCS, SF 5 , CF 3 , OCF 3 , NH 2 , a boronic ester, an unsubstituted or simply CN or simply or alkyl group having 1 to 15 carbon atoms substituted several times by
  • X 2 is F or OCF 3 and g is O, 1 or 2 and alkyl is as defined later
  • transition metal catalysts suitable for the hydroformylation in particular those of the transition metals rhodium (Rh), ruthenium (Ru) or cobalt (Co) are used.
  • the metal nuclei of the catalysts can be equipped with various ligands at the central atom of the transition metal, so with CO
  • the cyano-substituted representatives of formula IV are z. B. indirectly via the dihydropyrane INc accessible. These can be chlorinated in analogy to the chlorination of the unsubstituted 5,6-dihydro-4H-pyran with gaseous hydrochloric acid and then either with AgCN (BA Nelson et al., J. Org. Chem. (1956), 21, 798) or by means of trimethylsilyl cyanide in the presence of SnCl 2 (Reetz, M. et al., Tetrahedron (1983), 33, 961) to cyano compounds of formula IV.
  • the aldehydes via allylation of the carbonyl function, etherification of the alcohol with a propynyl radical and subsequent enyne metathesis, are a dihydropyran ring which is substituted by an optionally substituted ethenyl group (cf. EP 1482020 A1).
  • the optional substituent depends on the optional substitution of the allyl-Grignard compound used for the allylation.
  • the use of the aldehyde compounds according to formula II in this case is accordingly particularly characterized in that compounds of the formula Qa,
  • Tetrahydropyranaldehyden the following formulas A-G:
  • a 5 and A 6 such as A 1 , Z 5 and Z 6 such as Z 1 , f 0, 1 or 2, and e are as defined in a formula II. Depending on the procedure, the meanings of the variables are subject to the restrictions specified or directly apparent there.
  • a further aspect of the present invention are novel formyltetrahydropyrans of the formula II as defined above, which are preferably characterized in that, independently of one another, at least one of Z 1 , Z 2 , Z 3 in the molecule of a group -CF 2 CF 2 -, -CF 2 CH 2 -, -CH 2 CF 2 -, -CH 2 CH 2 CF 2 O-, -OCF 2 CH 2 CH 2 -, -CF 2 O- or -OCF 2 - corresponds to, or, that
  • the E isomer (trans) is preferred.
  • the alkenyl radical contains 2, 3, 4, 5, 6 or 7 carbon atoms and is vinyl, allyl, 1E-propenyl, 2-propenyl, 1E-butenyl, 1E-pentenyl, 1E-hexenyl, 1E-heptenyl , 2-propenyl,
  • Halogen in the context of the present invention for fluorine, chlorine, bromine or iodine.
  • Substituents or compounds may be present, for example, because they have an asymmetric center, so these are of of the present invention. It is understood that these compounds in isomerically pure form, for example as pure enantiomers, diastereomers, E or Z isomers, trans or cis isomers, or as a mixture of several isomers in any ratio, for example as a racemate, E - / Z
  • 0.135 mole (38.7 g) of (5) and 0.135 mole (16.1 g) of propargyl bromide are dissolved in 80 ml of tetrahydrofuran and made into a vigorously stirred emulsion of sodium hydroxide pellets (0.27 mole, 10.8 g), 0.5 ml of water, 40 ml of tetrahydrofuran and 6.75 mmol (2.46 g) of N-cetyl-N, N, N-trimethyl ammonium bromide, heated to 45 0 C and stirred for 16 h at this temperature. Then ice water is poured onto 1.5 l, the organic phase is separated off and the aqueous phase is extracted three times with MTB ether.
  • 0.2 g (7) are hydrogenated in 5 ml of methanol and 1 ml of toluene with 0.1 g of tris (triphenylphosphine) rhodium (l) chloride at 10 bar hydrogen pressure and 90 0 C for 6 h. After cooling, the reaction mixture is evaporated in vacuo and filtered through silica gel with toluene / heptane (3: 7). After evaporation, 0.15 g (8) of oil is obtained.
  • Homoallylic Alcohol Precursor by O-Alkylation with Ethyl-2 (Bromomethyl) acrylate For this purpose, 0.2 mol (8.0 g) of sodium hydride are added dropwise as a 60% suspension in 80 ml of tetrahydrofuran with stirring and external cooling with ice water with 0.2 mol (76.1 g) Homoallylalkohol in 80 ml of tetrahydrofuran under a nitrogen blanket, wherein the temperature is maintained at 20 0 C. After about 2 hours is the
  • Dihydropyranester (10) are hydrogenated in 300 ml of methanol and 60 ml of toluene at 10 bar hydrogen pressure and 100 ° C for 12 h with 2 g of tris (triphenylphosphine) rhodium (l) chloride.
  • DCCI dicyclohexylcarbodiimide
  • DAP 4-dimethylaminopyridine
  • the alcohol (30) is oxidized to the aldehyde (31) according to Swern. To do this
  • the dihydropyran (32) generated by metathesis is converted by hydroformylation to the aldehyde (33) analogously to Example 1 and is first reacted with the homoallylic alcohol (34) in an ene-carbonyl reaction to give the bromotetrahydropyran (35).
  • the homoallylic alcohol is synthesized via the acetate of the zinc alcohol (38) which can be prepared by conventional methods by reaction with gaseous formaldehyde in the presence of zinc dust and CoBr 2 .
  • the aldehyde (43) is then reacted with 2-ethyl-1, 3-propanediol to dioxane (4c) (see Example 3).
  • To this are dissolved 44.5 g (110 mmol) of the aldehyde (43) and 12.0 g (115 mmol) of the diol 2-ethyl-1,3-propanediol in 250 ml of toluene, 400 mg of p-toluenesulfonic acid monohydrate and until heated to complete conversion of the aldehyde (DC) under reflux at the water.
  • the cooled batch is washed three times with sat.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Liquid Crystal Substances (AREA)
  • Pyrane Compounds (AREA)

Abstract

L'invention concerne des formyltétrahydropyranes comportant des substituants mésogènes, ainsi leurs procédés de production et leur utilisation pour produire des dérivés de tétrahydropyrane substitués.
PCT/EP2006/004424 2005-05-25 2006-05-11 Formyltetrahydropyranes, leurs procedes de production et leur utilisation Ceased WO2006125529A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN2006800180648A CN101180285B (zh) 2005-05-25 2006-05-11 甲酰基四氢吡喃、其制备方法及其用途
KR1020077030222A KR101307585B1 (ko) 2005-05-25 2006-05-11 폼일테트라하이드로피란, 그의 제조 방법 및 액정 화합물의제조에서 그의 용도
JP2008512722A JP5366541B2 (ja) 2005-05-25 2006-05-11 ホルミルテトラヒドロピラン類、それの調製方法、および液晶化合物類の調製におけるそれの使用
DE112006000999T DE112006000999A5 (de) 2005-05-25 2006-05-11 Formyltetrahydrophyrane, Verfahren zu ihrer Herstellung sowie ihre Verwendung in der Herstellung von Flüssigkristallinen Verbindungen

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP05011321.6 2005-05-25
EP05011321 2005-05-25

Publications (1)

Publication Number Publication Date
WO2006125529A1 true WO2006125529A1 (fr) 2006-11-30

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PCT/EP2006/004424 Ceased WO2006125529A1 (fr) 2005-05-25 2006-05-11 Formyltetrahydropyranes, leurs procedes de production et leur utilisation

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JP (1) JP5366541B2 (fr)
KR (1) KR101307585B1 (fr)
CN (1) CN101180285B (fr)
DE (1) DE112006000999A5 (fr)
WO (1) WO2006125529A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7790247B2 (en) * 2006-10-04 2010-09-07 Merck Patent Gmbh Liquid-crystalline medium
US10174252B2 (en) 2015-02-24 2019-01-08 Jnc Corporation Liquid crystal composition and liquid crystal display device

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6435923B2 (ja) * 2014-03-07 2018-12-12 Jnc株式会社 ジヒドロピラン化合物、液晶組成物および液晶表示素子
JP6627515B2 (ja) 2015-02-06 2020-01-08 Jnc株式会社 ３，６−ジヒドロ−２ｈ−ピランを有する誘電率異方性が負の液晶性化合物、液晶組成物および液晶表示素子
JP6657611B2 (ja) * 2015-06-15 2020-03-04 Dic株式会社 カルボニル化合物の製造方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2786853A (en) * 1954-08-31 1957-03-26 Union Carbide & Carbon Corp 3, 4-dihydro-2h-pyran-2-yl-acyloxyaceto-nitriles and process for their preparation
DE3306960A1 (de) * 1983-02-28 1984-08-30 Merck Patent Gmbh, 6100 Darmstadt Tetrahydropyrane
WO1992010488A1 (fr) * 1990-12-14 1992-06-25 Basf Aktiengesellschaft Procede de fabrication de formyltetrahydropyrannes
US5149821A (en) * 1990-10-11 1992-09-22 Pfizer Inc Process and intermediates for optically active 3-formyltetrahydropyrans

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1254724A (en) * 1968-01-31 1971-11-24 Zaidan Hojin Biseibutsu New chemical compound useful as starting substance for amino sugars and process for producing it
CH626533A5 (fr) * 1978-01-20 1981-11-30 Firmenich & Cie
GB0020721D0 (en) * 2000-08-22 2000-10-11 Merck Sharp & Dohme Therapeutic agents
JP4718471B2 (ja) * 2003-05-27 2011-07-06 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 液晶化合物
ATE340836T1 (de) * 2003-05-27 2006-10-15 Merck Patent Gmbh Pyranderivate

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2786853A (en) * 1954-08-31 1957-03-26 Union Carbide & Carbon Corp 3, 4-dihydro-2h-pyran-2-yl-acyloxyaceto-nitriles and process for their preparation
DE3306960A1 (de) * 1983-02-28 1984-08-30 Merck Patent Gmbh, 6100 Darmstadt Tetrahydropyrane
US5149821A (en) * 1990-10-11 1992-09-22 Pfizer Inc Process and intermediates for optically active 3-formyltetrahydropyrans
WO1992010488A1 (fr) * 1990-12-14 1992-06-25 Basf Aktiengesellschaft Procede de fabrication de formyltetrahydropyrannes

Non-Patent Citations (12)

* Cited by examiner, † Cited by third party
Title
BIANCHI P ET AL: "On the selectivity of oxynitrilases towards alpha-oxygenated aldehydes", TETRAHEDRON, vol. 57, no. 11, 10 March 2001 (2001-03-10), pages 2213 - 2220, XP004230759 *
BUFFET M F ET AL: "Oxygen to carbon rearrangements of anomerically linked alkenols from tetrahydropyran derivatives: an investigation of the reaction mechanism via a double isotopic labelling crossover study", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, no. 12, 2000, pages 1815 - 1827, XP002392361 *
DE SELMS R C: "Benzimidazoles. I. 2-(Heterocyclic substituted) benzimidazoles", JOURNAL OF ORGANIC CHEMISTRY, vol. 27, no. 6, June 1962 (1962-06-01), pages 2163 - 2165, XP002392355 *
DEATON M V ET AL: "Yb(fod)3-promoted ene reactions of aldehydes with vinyl ethers", TETRAHEDRON LETTERS, vol. 34, no. 15, 9 April 1993 (1993-04-09), pages 2409 - 2412, XP002392358 *
KOCIENSKI P ET AL: "Allenol ether intermediates in the synthesis of 1,7-dioxaspiro[5.5]undec-4-enes and 1,6-dioxaspiro[4.5]dec-3-enes", SYNTHESIS, no. 11, November 1991 (1991-11-01), pages 1029 - 1038, XP002392353 *
MILNE J E ET AL: "A synthesis of alpha-lithiated enol ethers from alpha-arenesulfinyl enol ethers: Ni(0)- and Pd(0)-catalysed coupling of enol triflates and phosphates derived from lactones with sodium arenethiolates gives alpha-arenesulfanyl enol ethers", SYNTHESIS, no. 4, 18 March 2003 (2003-03-18), pages 584 - 592, XP002392360 *
POLO A ET AL: "Regioselective hydroformylation of cyclic vinyl and allyl ethers with rhodium catalysts . Crucial influence of the size of the phosphorus cocatalyst", ORGANOMETALLICS, vol. 11, no. 11, November 1992 (1992-11-01), pages 3525 - 3533, XP000602476 *
SCHULZ H ET AL: "Synthese und Umwandlungsprodukte des Acroleins", ANGEWANDTE CHEMIE, vol. 62, no. 5, 7 March 1950 (1950-03-07), pages 105 - 118, XP000653944 *
SILBERMAN H C: "New di-and tetrahydropyran derivatives", JOURNAL OF ORGANIC CHEMISTRY, vol. 25, no. 1, January 1960 (1960-01-01), pages 151 - 153, XP002392354 *
STETTER H ET AL: "Addition von Aldehyden an aktivierte Doppelbindungen, XXVIII. Herstellung und Reaktionen von alkoxy- und Acetoxy-2,5-diketonen", CHEMISCHE BERICHTE, vol. 114, no. 2, 4 February 1981 (1981-02-04), pages 581 - 596, XP002392356 *
SUTTON A E ET AL: "New tandem catalysis: preparation of cyclic enol ethers through a ruthenium-catalyzed ring-closing metathesis-olefin isomerization sequence", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 124, no. 45, 13 November 2002 (2002-11-13), pages 13390 - 13391, XP002392359 *
URBAN F J ET AL: "An efficient preparation of tetrahydropyran-(3R)- carboxaldehyde, a key intermediate for the synthesis of a novel 5-lipoxygenase inhibitor", TETRAHEDRON: ASYMMETRY, vol. 3, no. 6, June 1992 (1992-06-01), pages 731 - 734, XP002392357 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7790247B2 (en) * 2006-10-04 2010-09-07 Merck Patent Gmbh Liquid-crystalline medium
US10174252B2 (en) 2015-02-24 2019-01-08 Jnc Corporation Liquid crystal composition and liquid crystal display device

Also Published As

Publication number Publication date
DE112006000999A5 (de) 2008-06-19
KR20080019021A (ko) 2008-02-29
CN101180285B (zh) 2013-01-09
JP5366541B2 (ja) 2013-12-11
KR101307585B1 (ko) 2013-09-12
CN101180285A (zh) 2008-05-14
JP2009507759A (ja) 2009-02-26

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