JPH0466480B2 - - Google Patents

Info

Publication number: JPH0466480B2
Authority: JP; Japan
Prior art keywords: formula; lignan; diol compound; lactone; lower alkoxy
Prior art date: 1985-12-13
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.): Expired - Lifetime

Application number

JP60280523A

Other languages

English (en)

Japanese (ja)

Other versions

JPS62142170A (ja

Inventor

Yoichi Ishii

Takao Ikarya

Masahiko Saburi

Sadao Yoshikawa

Shintaro Kaji

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.)

Takasago International Corp

Original Assignee

Takasago Perfumery Industry Co

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.)

1985-12-13

Filing date

1985-12-13

Publication date

1992-10-23

1985-12-13 Application filed by Takasago Perfumery Industry Co filed Critical Takasago Perfumery Industry Co

1985-12-13 Priority to JP60280523A priority Critical patent/JPS62142170A/ja

1987-06-25 Publication of JPS62142170A publication Critical patent/JPS62142170A/ja

1992-10-23 Publication of JPH0466480B2 publication Critical patent/JPH0466480B2/ja

Status Granted legal-status Critical Current

Links

-1 methylenedioxy group Chemical group 0.000 claims description 25
229930013686 lignan Natural products 0.000 claims description 12
235000009408 lignans Nutrition 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
GTBPUYSGSDIIMM-UHFFFAOYSA-N phosphane;ruthenium Chemical compound P.[Ru] GTBPUYSGSDIIMM-UHFFFAOYSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
239000003054 catalyst Substances 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000000034 method Methods 0.000 description 7
150000008065 acid anhydrides Chemical class 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
BCJVBDBJSMFBRW-UHFFFAOYSA-N 4-diphenylphosphanylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BCJVBDBJSMFBRW-UHFFFAOYSA-N 0.000 description 3
BWHOZHOGCMHOBV-UHFFFAOYSA-N Benzalacetone Natural products CC(=O)C=CC1=CC=CC=C1 BWHOZHOGCMHOBV-UHFFFAOYSA-N 0.000 description 3
GRTJBNJOHNTQBO-UHFFFAOYSA-N [2-(2-diphenylphosphanylphenyl)phenyl]-diphenylphosphane Chemical compound C1=CC=CC=C1P(C=1C(=CC=CC=1)C=1C(=CC=CC=1)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 GRTJBNJOHNTQBO-UHFFFAOYSA-N 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
150000002596 lactones Chemical class 0.000 description 3
BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 3
229910010082 LiAlH Inorganic materials 0.000 description 2
AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 description 1
OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 1
241000238631 Hexapoda Species 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
235000005513 chalcones Nutrition 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000006356 dehydrogenation reaction Methods 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 1
229940114124 ferulic acid Drugs 0.000 description 1
KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 1
235000001785 ferulic acid Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 1
239000000203 mixture Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
VGARCGGLEUCMSB-UHFFFAOYSA-N phenyl(propyl)phosphane Chemical compound CCCPC1=CC=CC=C1 VGARCGGLEUCMSB-UHFFFAOYSA-N 0.000 description 1
229910000073 phosphorus hydride Inorganic materials 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
230000008635 plant growth Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Furan Compounds (AREA)

JP60280523A 1985-12-13 1985-12-13 リグナンラクトンの製造法 Granted JPS62142170A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP60280523A JPS62142170A (ja)	1985-12-13	1985-12-13	リグナンラクトンの製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP60280523A JPS62142170A (ja)	1985-12-13	1985-12-13	リグナンラクトンの製造法

Publications (2)

Publication Number	Publication Date
JPS62142170A JPS62142170A (ja)	1987-06-25
JPH0466480B2 true JPH0466480B2 (de)	1992-10-23

Family

ID=17626289

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP60280523A Granted JPS62142170A (ja)	1985-12-13	1985-12-13	リグナンラクトンの製造法

Country Status (1)

Country	Link
JP (1)	JPS62142170A (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ID18046A (id) *	1996-08-20	1998-02-19	Takeda Chemical Industries Ltd	Senyawa siklik campuran, pembuatan dan penngunaannya.
JP2003171372A (ja) *	2001-09-20	2003-06-20	Mitsubishi Chemicals Corp	カルボニル化合物の製造方法

1985
- 1985-12-13 JP JP60280523A patent/JPS62142170A/ja active Granted

Also Published As

Publication number	Publication date
JPS62142170A (ja)	1987-06-25

Publication	Publication Date	Title
JP3281920B2 (ja)	2002-05-13	アリルフラン化合物の製造方法
Tsuda et al.	1990	Nickel (0)-catalyzed cycloaddition of silyl diynes with carbon dioxide to silyl bicyclic. alpha.-pyrones
Ishii et al.	1986	Ruthenium complex catalyzed regioselective dehydrogenation of unsymmetrical. alpha.,. omega.-diols
Corey et al.	1964	The Wittig Reaction. I. Synthesis of β, γ-Unsaturated Acids
EP0418925A2 (de)	1991-03-27	Verfahren zur Herstellung von (S)-4-Hydroxymethyl-gamma-lacton
JPH0466480B2 (de)	1992-10-23
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EP0795552A1 (de)	1997-09-17	Verfahren zur Herstellung von 3-Formyl-tetrahydrofuran
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US3891678A (en)	1975-06-24	Preparation of alkylated or non-alkylated dihydrocoumarin together with the corresponding alkylated, or non-alkylated, coumarin
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Batu et al.	1979	Synthesis of isotubaic acid (rotenic acid)
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US5596110A (en)	1997-01-21	Process for the preparation of 3 β, 14 β-dihydroxyethianaldehyde