JPS643954B2 - - Google Patents
Info
- Publication number
- JPS643954B2 JPS643954B2 JP55108348A JP10834880A JPS643954B2 JP S643954 B2 JPS643954 B2 JP S643954B2 JP 55108348 A JP55108348 A JP 55108348A JP 10834880 A JP10834880 A JP 10834880A JP S643954 B2 JPS643954 B2 JP S643954B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- trimethylcyclohexenyl
- acetic acid
- dihydroactinidiolide
- reaction
- 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.)
- Expired
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- IMKHDCBNRDRUEB-LLVKDONJSA-N dihydroactinidiolide Chemical compound C1CCC(C)(C)C2=CC(=O)O[C@@]21C IMKHDCBNRDRUEB-LLVKDONJSA-N 0.000 claims description 5
- IMKHDCBNRDRUEB-UHFFFAOYSA-N Dihydroactinidiolide Natural products C1CCC(C)(C)C2=CC(=O)OC21C IMKHDCBNRDRUEB-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 235000011054 acetic acid Nutrition 0.000 description 5
- 238000005868 electrolysis reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- -1 2,6,6-trimethylcyclohexenyl Chemical class 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000208125 Nicotiana Species 0.000 description 3
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 244000269722 Thea sinensis Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VYNZUXSDEVGYGP-UHFFFAOYSA-N (2,3,3-trimethylcyclohexen-1-yl) acetate Chemical compound C(C)(=O)OC1=C(C(CCC1)(C)C)C VYNZUXSDEVGYGP-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000006468 Thea sinensis Nutrition 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001579 beta-carotenes Chemical class 0.000 description 1
- 235000020279 black tea Nutrition 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
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- YWWZCHLUQSHMCL-UHFFFAOYSA-N diphenyl diselenide Chemical compound C=1C=CC=CC=1[Se][Se]C1=CC=CC=C1 YWWZCHLUQSHMCL-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 235000009569 green tea Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000005657 iodolactonization reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003726 retinal derivatives Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10834880A JPS5735583A (en) | 1980-08-08 | 1980-08-08 | Production of d1-dihydroactinidiolide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10834880A JPS5735583A (en) | 1980-08-08 | 1980-08-08 | Production of d1-dihydroactinidiolide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5735583A JPS5735583A (en) | 1982-02-26 |
| JPS643954B2 true JPS643954B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-01-24 |
Family
ID=14482418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10834880A Granted JPS5735583A (en) | 1980-08-08 | 1980-08-08 | Production of d1-dihydroactinidiolide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5735583A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0363548B1 (en) * | 1988-10-10 | 1994-03-23 | International Business Machines Corporation | Method of breaking a plate-like workpiece such as a semi-conductor wafer, and device for breaking said workpiece sandwiched between two foils |
-
1980
- 1980-08-08 JP JP10834880A patent/JPS5735583A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5735583A (en) | 1982-02-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6843120B2 (ja) | （４ｓ）−４−（４−シアノ−２−メトキシフェニル）−５−エトキシ−２，８−ジメチル−１，４−ジヒドロ−１，６−ナフチリジン−３−カルボキサミドの調製方法および電気化学的方法による（４ｓ）−４−（４−シアノ−２−メトキシフェニル）−５−エトキシ−２，８−ジメチル−１，４−ジヒドロ−１，６−ナフチリジン−３−カルボキサミドの回収 | |
| JP4765623B2 (ja) | ２−クロロ−５−フルオロ−３−置換ピリジンまたはその塩の製造方法 | |
| Fuchigami et al. | Electrolytic reactions of fluoro organic compounds. 7. Anodic methoxylation and acetoxylation of 2, 2, 2-trifluoroethyl sulfides. Preparation of highly useful trifluoromethylated building blocks | |
| JPS60228441A (ja) | 光学的に活性なα―アリルアルカノイック酸の製造方法 | |
| Senboku et al. | Some mechanistic studies on electrochemical carboxylation of flavones to yield flavanone-2-carboxylic acids | |
| JPS643954B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| EP2298756A1 (en) | Method for producing 3-methyl-2-thiophenecarboxylic acid | |
| US4629541A (en) | Process for the electrosynthesis of ketones | |
| CA2254788C (en) | Process for preparing phthalides | |
| US4499265A (en) | Process for preparing 3-exo-methylenecepham derivatives | |
| US4637863A (en) | Process for the electrosynthesis of alcohols and of epoxy compounds | |
| US4988416A (en) | Process for the electrosynthesis of aldehydes | |
| HU178581B (en) | Process for producing 6-chloro-alpha-methyl-carbasole-2-acetic acid | |
| CN119332255B (zh) | 电化学合成芦竹碱类衍生物的方法 | |
| JP4030164B2 (ja) | テトラハイドロピリジン誘導体及びその製造方法 | |
| Skowronski et al. | New chemical conversions of 5-hydroxymethylfurfural and the electrochemical oxidation of its derivatives | |
| JPS6247181B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JPH0116917B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| CN101244992A (zh) | 4-氧代-β-紫罗兰酮的简便合成方法 | |
| JP2540588B2 (ja) | トロポン及びアルコキシトロポン誘導体の製造法 | |
| JPS6039183A (ja) | テレフタルアルデヒドの製造方法 | |
| JPS632249B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| CN117120409A (zh) | 用于生产naa和(s)-naa的方法 | |
| JP2003508359A (ja) | 接触脱水素反応によるジベンゾスベレノン誘導体の製造 | |
| JPH03109355A (ja) | ２，２，５，５―テトラメチルシクロペンタンカルボン酸誘導体の製造方法およびその中間体 |