JPS6229581A - α又はβ−置換−γ−ヒドロキシブテノライドの製造法 - Google Patents
α又はβ−置換−γ−ヒドロキシブテノライドの製造法Info
- Publication number
- JPS6229581A JPS6229581A JP16936785A JP16936785A JPS6229581A JP S6229581 A JPS6229581 A JP S6229581A JP 16936785 A JP16936785 A JP 16936785A JP 16936785 A JP16936785 A JP 16936785A JP S6229581 A JPS6229581 A JP S6229581A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- group
- photosensitizer
- oxygen
- 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.)
- Granted
Links
- -1 beta-substituted-gamma-hydroxybutenolide Chemical class 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 230000001678 irradiating effect Effects 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 abstract description 9
- 239000001301 oxygen Substances 0.000 abstract description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 4
- VOFXXOPWCBSPAA-UPXBXCCMSA-N (+)-Strigol Natural products O(/C=C/1\C(=O)O[C@H]2[C@@H]\1CC=1[C@H](O)CCC(C)(C)C2=1)[C@@H]1OC(=O)C(C)=C1 VOFXXOPWCBSPAA-UPXBXCCMSA-N 0.000 abstract description 3
- ARGBKKMNXCMJSK-UHFFFAOYSA-N Strigol Natural products CC1C=C(OC=C2/C3CC4=C(C3OC2=O)C(C)(C)CCC4O)OC1=O ARGBKKMNXCMJSK-UHFFFAOYSA-N 0.000 abstract description 3
- VOFXXOPWCBSPAA-KCNJUGRMSA-N strigol Chemical compound O1C(=O)C(C)=C[C@@H]1O\C=C/1C(=O)O[C@@H]2C(C(C)(C)CC[C@@H]3O)=C3C[C@@H]2\1 VOFXXOPWCBSPAA-KCNJUGRMSA-N 0.000 abstract description 3
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 229930002875 chlorophyll Natural products 0.000 abstract description 2
- 235000019804 chlorophyll Nutrition 0.000 abstract description 2
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 abstract description 2
- 229960000907 methylthioninium chloride Drugs 0.000 abstract description 2
- 230000001737 promoting effect Effects 0.000 abstract description 2
- 230000007226 seed germination Effects 0.000 abstract description 2
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical compound C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 abstract 1
- 230000002757 inflammatory effect Effects 0.000 abstract 1
- FGJIDQWRRLDGDB-CPIXEKRISA-N manoalide Chemical compound C=1([C@@H](O[C@H](CC=1)C=1[C@@H](OC(=O)C=1)O)O)CC\C=C(/C)CCC1=C(C)CCCC1(C)C FGJIDQWRRLDGDB-CPIXEKRISA-N 0.000 abstract 1
- FGJIDQWRRLDGDB-GMKZXUHWSA-N manoalide Natural products CC(=CCCC1=CC[C@@H](O[C@H]1O)C2=CC(=O)O[C@H]2O)CCC3=C(C)CCCC3(C)C FGJIDQWRRLDGDB-GMKZXUHWSA-N 0.000 abstract 1
- 239000005445 natural material Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- JZQBAGOECGRTSA-UHFFFAOYSA-N 3-hydroxy-2h-furan-5-one Chemical class OC1=CC(=O)OC1 JZQBAGOECGRTSA-UHFFFAOYSA-N 0.000 description 4
- IICCLYANAQEHCI-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 IICCLYANAQEHCI-UHFFFAOYSA-N 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229930014626 natural product Natural products 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 229930187593 rose bengal Natural products 0.000 description 3
- 229940081623 rose bengal Drugs 0.000 description 3
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- OZTKUZMZLPEQQW-IIZANFQQSA-N (2s)-2-[[(2s)-2-[[(2s)-1-[2-[[(2s)-2-[[(2s)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylsulfanylbutanoyl]amino]acetyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoic acid Chemical compound C([C@H](N)C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 OZTKUZMZLPEQQW-IIZANFQQSA-N 0.000 description 1
- SQEBMLCQNJOCBG-HVHJFMEUSA-N (5s)-3-(hydroxymethyl)-5-methoxy-4-methyl-5-[(e)-2-phenylethenyl]furan-2-one Chemical group C=1C=CC=CC=1/C=C/[C@]1(OC)OC(=O)C(CO)=C1C SQEBMLCQNJOCBG-HVHJFMEUSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- YQGOJNYOYNNSMM-UHFFFAOYSA-N eosin Chemical compound [Na+].OC(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C(O)=C(Br)C=C21 YQGOJNYOYNNSMM-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HRWRZEKRKZRDRW-UHFFFAOYSA-N furan-2-yl(trimethyl)silane Chemical compound C[Si](C)(C)C1=CC=CO1 HRWRZEKRKZRDRW-UHFFFAOYSA-N 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000005389 magnetism Effects 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 108700028731 phorphin Proteins 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 230000002165 photosensitisation Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
Landscapes
- Furan Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16936785A JPS6229581A (ja) | 1985-07-30 | 1985-07-30 | α又はβ−置換−γ−ヒドロキシブテノライドの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16936785A JPS6229581A (ja) | 1985-07-30 | 1985-07-30 | α又はβ−置換−γ−ヒドロキシブテノライドの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6229581A true JPS6229581A (ja) | 1987-02-07 |
| JPH0564632B2 JPH0564632B2 (enrdf_load_stackoverflow) | 1993-09-16 |
Family
ID=15885269
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16936785A Granted JPS6229581A (ja) | 1985-07-30 | 1985-07-30 | α又はβ−置換−γ−ヒドロキシブテノライドの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6229581A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5082954A (en) * | 1987-06-08 | 1992-01-21 | Allergan, Inc. | Intermediates and processes for preparing 4-substituted 2-5(H)-furanones as anti-inflammatory agents |
-
1985
- 1985-07-30 JP JP16936785A patent/JPS6229581A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5082954A (en) * | 1987-06-08 | 1992-01-21 | Allergan, Inc. | Intermediates and processes for preparing 4-substituted 2-5(H)-furanones as anti-inflammatory agents |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0564632B2 (enrdf_load_stackoverflow) | 1993-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |