JPH0466479B2 - - Google Patents

Info

Publication number: JPH0466479B2
Authority: JP; Japan
Prior art keywords: lignan; acid anhydride; lactone; formula; dotted line
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

JP60280522A

Other languages

English (en)

Japanese (ja)

Other versions

JPS62142169A (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 JP60280522A priority Critical patent/JPS62142169A/ja

1987-06-25 Publication of JPS62142169A publication Critical patent/JPS62142169A/ja

1992-10-23 Publication of JPH0466479B2 publication Critical patent/JPH0466479B2/ja

Status Granted legal-status Critical Current

Links

-1 methylenedioxy group Chemical group 0.000 claims description 17
229930013686 lignan Natural products 0.000 claims description 14
235000009408 lignans Nutrition 0.000 claims description 14
150000008065 acid anhydrides Chemical class 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
GTBPUYSGSDIIMM-UHFFFAOYSA-N phosphane;ruthenium Chemical compound P.[Ru] GTBPUYSGSDIIMM-UHFFFAOYSA-N 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
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 1
238000000034 method Methods 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
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 6
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 4
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
238000006243 chemical reaction Methods 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
YMGOOHXUOWZQOE-UHFFFAOYSA-N taiwanin C Chemical compound C1=C2OCOC2=CC(C=2C3=CC=4OCOC=4C=C3C=C3COC(C=23)=O)=C1 YMGOOHXUOWZQOE-UHFFFAOYSA-N 0.000 description 4
LCDDWBRDCVIICN-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-1h-benzo[f][2]benzofuran-3-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=C(C(=O)OC2)C2=CC2=CC(OC)=C(OC)C=C12 LCDDWBRDCVIICN-UHFFFAOYSA-N 0.000 description 3
PJLRAQVYTOCNHT-UHFFFAOYSA-N 5-(3,4-dimethoxyphenyl)-8h-[2]benzofuro[5,6-f][1,3]benzodioxol-6-one Chemical compound C1=C(OC)C(OC)=CC=C1C(C1=C2)=C(C(=O)OC3)C3=CC1=CC1=C2OCO1 PJLRAQVYTOCNHT-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
BQPUGGCSGFPVKS-UHFFFAOYSA-N Chinensin Natural products COc1ccc(cc1OC)c2c3OCOc3cc4cc5COC(=O)c5cc24 BQPUGGCSGFPVKS-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
230000000694 effects Effects 0.000 description 3
150000002596 lactones Chemical class 0.000 description 3
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
239000000203 mixture Substances 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
LUPBOBWJAIWMIH-UHFFFAOYSA-N retrohelioxanthine Natural products C1=C2OCOC2=CC(C=2C3=C4OCOC4=CC=C3C=C3COC(C=23)=O)=C1 LUPBOBWJAIWMIH-UHFFFAOYSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
GBYROJNZMZOSDJ-UHFFFAOYSA-N taiwanin E methyl ether Natural products C12=CC=3OCOC=3C=C2C(OC)=C(OCC2=O)C2=C1C1=CC=C(OCO2)C2=C1 GBYROJNZMZOSDJ-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
241000238631 Hexapoda Species 0.000 description 1
229910010082 LiAlH Inorganic materials 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-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
244000309464 bull Species 0.000 description 1
238000004587 chromatography analysis 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
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
238000010438 heat treatment Methods 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 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
230000001737 promoting effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
125000003944 tolyl group Chemical group 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

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

JP60280522A 1985-12-13 1985-12-13 リグナンラクトンの製造法 Granted JPS62142169A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP60280522A JPS62142169A (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
JP60280522A JPS62142169A (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
JPS62142169A JPS62142169A (ja)	1987-06-25
JPH0466479B2 true JPH0466479B2 (de)	1992-10-23

Family

ID=17626275

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP60280522A Granted JPS62142169A (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)	JPS62142169A (de)

Families Citing this family (1)

* 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.

1985
- 1985-12-13 JP JP60280522A patent/JPS62142169A/ja active Granted

Also Published As

Publication number	Publication date
JPS62142169A (ja)	1987-06-25

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