KR20180018830A - 치환된 전자 풍부 다이페닐아세틸렌의 제조 방법 - Google Patents
치환된 전자 풍부 다이페닐아세틸렌의 제조 방법 Download PDFInfo
- Publication number
- KR20180018830A KR20180018830A KR1020187003692A KR20187003692A KR20180018830A KR 20180018830 A KR20180018830 A KR 20180018830A KR 1020187003692 A KR1020187003692 A KR 1020187003692A KR 20187003692 A KR20187003692 A KR 20187003692A KR 20180018830 A KR20180018830 A KR 20180018830A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- phenyl
- alkyl
- branched
- linear
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 27
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical class C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 title abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 235000021286 stilbenes Nutrition 0.000 claims abstract description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 30
- 125000004122 cyclic group Chemical group 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 17
- 150000001629 stilbenes Chemical class 0.000 claims description 9
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000002638 heterogeneous catalyst Substances 0.000 claims description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 6
- -1 tetrahydropyrryl Chemical group 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 2
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 2
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000001608 tolans Chemical class 0.000 abstract description 5
- 239000007858 starting material Substances 0.000 abstract description 3
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 abstract 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 9
- 238000005984 hydrogenation reaction Methods 0.000 description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 4
- 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 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000002815 homogeneous catalyst Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- SYSZENVIJHPFNL-UHFFFAOYSA-N (alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform B (protein) Chemical compound COC1=CC=C(I)C=C1 SYSZENVIJHPFNL-UHFFFAOYSA-N 0.000 description 2
- HVXBOLULGPECHP-WAYWQWQTSA-N Combretastatin A4 Chemical compound C1=C(O)C(OC)=CC=C1\C=C/C1=CC(OC)=C(OC)C(OC)=C1 HVXBOLULGPECHP-WAYWQWQTSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 2
- LUKBXSAWLPMMSZ-OWOJBTEDSA-N Trans-resveratrol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 LUKBXSAWLPMMSZ-OWOJBTEDSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229960005537 combretastatin A-4 Drugs 0.000 description 2
- HVXBOLULGPECHP-UHFFFAOYSA-N combretastatin A4 Natural products C1=C(O)C(OC)=CC=C1C=CC1=CC(OC)=C(OC)C(OC)=C1 HVXBOLULGPECHP-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000003495 polar organic solvent Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 235000021283 resveratrol Nutrition 0.000 description 2
- 229940016667 resveratrol Drugs 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 0 *c1cc(*)c(*)cc1 Chemical compound *c1cc(*)c(*)cc1 0.000 description 1
- GDHNBPHYVRHYCC-PLNGDYQASA-N 1,3-dimethoxy-5-[(z)-2-(4-methoxyphenyl)ethenyl]benzene Chemical compound C1=CC(OC)=CC=C1\C=C/C1=CC(OC)=CC(OC)=C1 GDHNBPHYVRHYCC-PLNGDYQASA-N 0.000 description 1
- HUSBBWQIJMRKLI-UHFFFAOYSA-N 1-ethynyl-3,5-dimethoxybenzene Chemical compound COC1=CC(OC)=CC(C#C)=C1 HUSBBWQIJMRKLI-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- 102000004243 Tubulin Human genes 0.000 description 1
- 108090000704 Tubulin Proteins 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 238000003804 extraction from natural source Methods 0.000 description 1
- 238000009904 heterogeneous catalytic hydrogenation reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/20—Preparation of ethers by reactions not forming ether-oxygen bonds by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09166121 | 2009-07-22 | ||
| EP09166121.5 | 2009-07-22 | ||
| PCT/EP2010/060569 WO2011009888A2 (en) | 2009-07-22 | 2010-07-21 | Process for the production of substituted electron rich diphenylacetylenes |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020127004475A Division KR20120039033A (ko) | 2009-07-22 | 2010-07-21 | 치환된 전자 풍부 다이페닐아세틸렌의 제조 방법 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20180018830A true KR20180018830A (ko) | 2018-02-21 |
Family
ID=43244855
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020127004475A Ceased KR20120039033A (ko) | 2009-07-22 | 2010-07-21 | 치환된 전자 풍부 다이페닐아세틸렌의 제조 방법 |
| KR1020187003692A Withdrawn KR20180018830A (ko) | 2009-07-22 | 2010-07-21 | 치환된 전자 풍부 다이페닐아세틸렌의 제조 방법 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020127004475A Ceased KR20120039033A (ko) | 2009-07-22 | 2010-07-21 | 치환된 전자 풍부 다이페닐아세틸렌의 제조 방법 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20130131390A1 (enExample) |
| EP (1) | EP2456742A2 (enExample) |
| JP (1) | JP2012533600A (enExample) |
| KR (2) | KR20120039033A (enExample) |
| CN (1) | CN102625792A (enExample) |
| BR (1) | BR112012001511A2 (enExample) |
| IN (1) | IN2012DN00578A (enExample) |
| WO (1) | WO2011009888A2 (enExample) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004505998A (ja) * | 2000-08-15 | 2004-02-26 | ノースイースタン、オハイオ、ユニバーシティーズ、カレッジ、オブ、メディシン | ヘルペスウイルスまたはＮｅｉｓｓｅｒｉａｇｏｎｏｒｒｈｏｅａｅに感染した患者を処置する方法 |
| JP4778710B2 (ja) * | 2005-01-14 | 2011-09-21 | 宇部興産株式会社 | パラジウム触媒が充填されたフローリアクターを用いるカップリング反応 |
| US8680142B2 (en) * | 2007-06-20 | 2014-03-25 | Kent State University | Ascorbate, vitamin K3 and hydroxytolans in the treatment of cancer |
| KR100878394B1 (ko) * | 2008-01-31 | 2009-01-13 | 한림대학교 산학협력단 | Ｐｉｃｅａｔａｎｎｏｌ의 합성 |
-
2010
- 2010-07-21 WO PCT/EP2010/060569 patent/WO2011009888A2/en not_active Ceased
- 2010-07-21 US US13/386,385 patent/US20130131390A1/en not_active Abandoned
- 2010-07-21 IN IN578DEN2012 patent/IN2012DN00578A/en unknown
- 2010-07-21 EP EP10740576A patent/EP2456742A2/en not_active Withdrawn
- 2010-07-21 KR KR1020127004475A patent/KR20120039033A/ko not_active Ceased
- 2010-07-21 CN CN2010800338198A patent/CN102625792A/zh active Pending
- 2010-07-21 JP JP2012521031A patent/JP2012533600A/ja active Pending
- 2010-07-21 BR BR112012001511A patent/BR112012001511A2/pt not_active IP Right Cessation
- 2010-07-21 KR KR1020187003692A patent/KR20180018830A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| BR112012001511A2 (pt) | 2019-09-24 |
| WO2011009888A2 (en) | 2011-01-27 |
| KR20120039033A (ko) | 2012-04-24 |
| EP2456742A2 (en) | 2012-05-30 |
| US20130131390A1 (en) | 2013-05-23 |
| JP2012533600A (ja) | 2012-12-27 |
| CN102625792A (zh) | 2012-08-01 |
| WO2011009888A3 (en) | 2011-10-06 |
| IN2012DN00578A (enExample) | 2015-06-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A107 | Divisional application of patent | ||
| PA0104 | Divisional application for international application |
Comment text: Divisional Application for International Patent Patent event code: PA01041R01D Patent event date: 20180206 Application number text: 1020127004475 Filing date: 20120221 |
|
| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |