JPS606678A - ２−フエニルチオ−５−ヒドロキシ−５−置換−２−ペンテン−４−オリド類及びその製法 - Google Patents
２−フエニルチオ−５−ヒドロキシ−５−置換−２−ペンテン−４−オリド類及びその製法Info
- Publication number
- JPS606678A JPS606678A JP11436283A JP11436283A JPS606678A JP S606678 A JPS606678 A JP S606678A JP 11436283 A JP11436283 A JP 11436283A JP 11436283 A JP11436283 A JP 11436283A JP S606678 A JPS606678 A JP S606678A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- phenylthio
- olide
- compound
- hydroxy
- 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 2-phenylthio-5-hydroxy-5-substituted-2-penten-4-olide Chemical class 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 229910003002 lithium salt Inorganic materials 0.000 claims abstract description 8
- 159000000002 lithium salts Chemical class 0.000 claims abstract description 8
- NYSGNNULGPBKOK-UHFFFAOYSA-N 4-phenylsulfanyl-2h-furan-5-one Chemical compound O=C1OCC=C1SC1=CC=CC=C1 NYSGNNULGPBKOK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 37
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 239000011261 inert gas Substances 0.000 abstract description 4
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003960 organic solvent Substances 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 239000002917 insecticide Substances 0.000 abstract description 3
- 239000012298 atmosphere Substances 0.000 abstract description 2
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000000855 fungicidal effect Effects 0.000 abstract 1
- 239000000417 fungicide Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- BYKMLQPPSSCYIL-SECBINFHSA-N (3R)-3-phenylsulfanyloxolan-2-one Chemical compound O=C1OCC[C@H]1Sc1ccccc1 BYKMLQPPSSCYIL-SECBINFHSA-N 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- KVBRVPBLWSRAEL-UHFFFAOYSA-N 2-[hydroxy(phenyl)methyl]-4-phenylsulfanyl-2h-furan-5-one Chemical compound C=1C=CC=CC=1C(O)C(C=1)OC(=O)C=1SC1=CC=CC=C1 KVBRVPBLWSRAEL-UHFFFAOYSA-N 0.000 description 1
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241001432959 Chernes Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- BGLUXFNVVSVEET-UHFFFAOYSA-N beta-angelica lactone Chemical class CC1OC(=O)C=C1 BGLUXFNVVSVEET-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- VIHAEDVKXSOUAT-UHFFFAOYSA-N but-2-en-4-olide Chemical compound O=C1OCC=C1 VIHAEDVKXSOUAT-UHFFFAOYSA-N 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
- QBZXOWQOWPHHRA-UHFFFAOYSA-N lithium;ethane Chemical compound [Li+].[CH2-]C QBZXOWQOWPHHRA-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- UYYCVBASZNFFRX-UHFFFAOYSA-N n-propan-2-ylcyclohexanamine Chemical compound CC(C)NC1CCCCC1 UYYCVBASZNFFRX-UHFFFAOYSA-N 0.000 description 1
- QEHKBHWEUPXBCW-UHFFFAOYSA-N nitrogen trichloride Chemical compound ClN(Cl)Cl QEHKBHWEUPXBCW-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
Landscapes
- Furan Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11436283A JPS606678A (ja) | 1983-06-27 | 1983-06-27 | ２−フエニルチオ−５−ヒドロキシ−５−置換−２−ペンテン−４−オリド類及びその製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11436283A JPS606678A (ja) | 1983-06-27 | 1983-06-27 | ２−フエニルチオ−５−ヒドロキシ−５−置換−２−ペンテン−４−オリド類及びその製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS606678A true JPS606678A (ja) | 1985-01-14 |
| JPH0434552B2 JPH0434552B2 (enrdf_load_stackoverflow) | 1992-06-08 |
Family
ID=14635818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11436283A Granted JPS606678A (ja) | 1983-06-27 | 1983-06-27 | ２−フエニルチオ−５−ヒドロキシ−５−置換−２−ペンテン−４−オリド類及びその製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS606678A (enrdf_load_stackoverflow) |
-
1983
- 1983-06-27 JP JP11436283A patent/JPS606678A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0434552B2 (enrdf_load_stackoverflow) | 1992-06-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS606678A (ja) | ２−フエニルチオ−５−ヒドロキシ−５−置換−２−ペンテン−４−オリド類及びその製法 | |
| JPS6236374A (ja) | チオテトロン酸の製造方法 | |
| JPH0434551B2 (enrdf_load_stackoverflow) | ||
| Koldobskii et al. | 1-Bromo-2-trifluoroacetylcyclobutenes as novel building blocks for the construction of trifluoromethyl substituted heterocycles. Part 3: Synthesis of trifluoromethylsubstituted pyridines, condensed with cyclobutene moieties | |
| JPH0338583A (ja) | １‐（４‐テトラヒドロピラニル）‐１‐ブテン‐３‐オンの製造方法 | |
| JPS606681A (ja) | （ζ）−５−置換イリデン−３−フエニルチオ−２−オキソ−３−チオレン類及びその製法 | |
| JPS6277370A (ja) | 含フツ素ピラゾ−ル誘導体 | |
| JP2791488B2 (ja) | ピロール誘導体の製造方法 | |
| JP3787018B2 (ja) | ３，４−ジヒドロ−α−ピロン類の製造方法 | |
| JPH06228090A (ja) | 殺虫、殺ダニ、殺線虫性２−アリール−５−トリフルオロメチルピロール化合物の製造方法 | |
| JPS62198663A (ja) | ５−ブロモピリドン−３−カルボキサミド化合物の製法 | |
| JP2006527164A (ja) | 新規なハロゲン置換された活性メチレン化合物 | |
| JPH03264557A (ja) | フッ素含有化合物 | |
| JPH04270241A (ja) | β−ケトエステルの製造方法 | |
| CN110256479A (zh) | 一种含硅酰基骨架的手性吡咯烷衍生物及其制备方法 | |
| JPH03127779A (ja) | アニリノピリミジン誘導体の製造法 | |
| JP2003267911A (ja) | ２−フルオロ安息香酸誘導体の製造方法 | |
| JPS62175456A (ja) | ５−アレ−ンスルホニルアルカンアミド誘導体 | |
| JPH09255641A (ja) | 光学活性フェニルケトン誘導体、および製造方法 | |
| JPH04270244A (ja) | β−ケトエステルの製法 | |
| JPS5927856A (ja) | α−クロロアセトアミド化合物 | |
| JPH0543692B2 (enrdf_load_stackoverflow) | ||
| JPS61137860A (ja) | １，４−ジヒドロピリジン酸誘導体の製造法 | |
| JPH0240078B2 (ja) | Jiarukiruhosuhonaatojudotaioyobisonoseizoho | |
| JPS58144386A (ja) | β−ラクタム化合物の製造法 |