CN1778779A - 1-aryl (group) - 1 - ethylenialkene and production thereof - Google Patents
1-aryl (group) - 1 - ethylenialkene and production thereof Download PDFInfo
- Publication number
- CN1778779A CN1778779A CN 200410084469 CN200410084469A CN1778779A CN 1778779 A CN1778779 A CN 1778779A CN 200410084469 CN200410084469 CN 200410084469 CN 200410084469 A CN200410084469 A CN 200410084469A CN 1778779 A CN1778779 A CN 1778779A
- Authority
- CN
- China
- Prior art keywords
- aryl
- group
- ethylenialkene
- compound
- milligrams
- 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 arene halide Chemical class 0.000 claims abstract description 28
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000002608 ionic liquid Substances 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims description 39
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 28
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 20
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 16
- 235000010290 biphenyl Nutrition 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 10
- 239000001294 propane Substances 0.000 claims description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 9
- 229910052763 palladium Inorganic materials 0.000 claims description 9
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 239000012485 toluene extract Substances 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229940078494 nickel acetate Drugs 0.000 claims description 3
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 3
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 claims description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
- 239000001273 butane Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 2
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims description 2
- 150000002941 palladium compounds Chemical class 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 4
- 238000003912 environmental pollution Methods 0.000 abstract description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 238000001816 cooling Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- AIYYMMQIMJOTBM-UHFFFAOYSA-L nickel(ii) acetate Chemical class [Ni+2].CC([O-])=O.CC([O-])=O AIYYMMQIMJOTBM-UHFFFAOYSA-L 0.000 description 3
- UUZYFBXKWIQKTF-UHFFFAOYSA-N 2-(3-bromophenyl)acetonitrile Chemical compound BrC1=CC=CC(CC#N)=C1 UUZYFBXKWIQKTF-UHFFFAOYSA-N 0.000 description 2
- APSMUYYLXZULMS-UHFFFAOYSA-N 2-bromonaphthalene Chemical compound C1=CC=CC2=CC(Br)=CC=C21 APSMUYYLXZULMS-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000004768 bromobenzenes Chemical class 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-Bis(diphenylphosphino)propane Substances C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 1
- WYECURVXVYPVAT-UHFFFAOYSA-N 1-(4-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Br)C=C1 WYECURVXVYPVAT-UHFFFAOYSA-N 0.000 description 1
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N cinnamyl alcohol Chemical class OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
- 150000001935 cyclohexenes Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000005838 radical anions Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2004100844694A CN100360481C (en) | 2004-11-18 | 2004-11-18 | 1-aryl (group) - 1 - ethylenialkene and production thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CNB2004100844694A CN100360481C (en) | 2004-11-18 | 2004-11-18 | 1-aryl (group) - 1 - ethylenialkene and production thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1778779A true CN1778779A (en) | 2006-05-31 |
CN100360481C CN100360481C (en) | 2008-01-09 |
Family
ID=36769245
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB2004100844694A Expired - Fee Related CN100360481C (en) | 2004-11-18 | 2004-11-18 | 1-aryl (group) - 1 - ethylenialkene and production thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN100360481C (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100564333C (en) * | 2007-11-23 | 2009-12-02 | 浙江工业大学 | A kind of synthetic method of 1-aryl (group)-1-ethylenialkene compounds |
CN106542950A (en) * | 2016-10-26 | 2017-03-29 | 梧州学院 | A kind of method for preparing limonene by 3 carenes |
-
2004
- 2004-11-18 CN CNB2004100844694A patent/CN100360481C/en not_active Expired - Fee Related
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100564333C (en) * | 2007-11-23 | 2009-12-02 | 浙江工业大学 | A kind of synthetic method of 1-aryl (group)-1-ethylenialkene compounds |
CN106542950A (en) * | 2016-10-26 | 2017-03-29 | 梧州学院 | A kind of method for preparing limonene by 3 carenes |
CN106542950B (en) * | 2016-10-26 | 2019-03-26 | 梧州学院 | A method of limonene is prepared by 3- carene |
Also Published As
Publication number | Publication date |
---|---|
CN100360481C (en) | 2008-01-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Enders et al. | Direct organocatalytic α-fluorination of aldehydes and ketones | |
Qu et al. | Ligand‐Free Reusable Palladium‐Catalyzed Heck‐Type Coupling Reactions of Hypervalent Iodine Reagents under Mild Conditions | |
Ren et al. | Cu (OTf) 2-catalyzed arylmethylation of terminal alkynes with benzylic alcohols under ligand-, base-, and additive-free reaction conditions | |
JP2011236208A (en) | Process for producing c1-c4 alkyl nitrite | |
Levi Knippel et al. | A General Strategy for the Asymmetric Preparation of α‐Stereogenic Allyl Silanes, Germanes, and Boronate Esters via Dual Copper Hydride‐and Palladium‐Catalysis | |
CN1778779A (en) | 1-aryl (group) - 1 - ethylenialkene and production thereof | |
Miyamoto et al. | Synthesis of 9, 10-diarylanthracenes via Mg (TMP) 2· 2LiCl-mediated benzyne generation/[4+ 2] cycloaddition and deoxygenation of 9, 10-epoxyanthracene intermediates | |
CN116535287B (en) | Synthesis method of 1, 3-pentachloropropane | |
Kitamura et al. | 2-Azido-1, 3-dimethylimidazolinium chloride: an efficient diazo transfer reagent for 1, 3-dicarbonyl compounds | |
Kopp et al. | Preparation of polyfunctional amines by the addition of functionalized organomagnesium reagents to nitrosoarenes | |
Xin et al. | Water-promoted Suzuki reaction in room temperature ionic liquids | |
CN1284756C (en) | Process for preparing 2-aryl allyl alcohol | |
Korn et al. | New cobalt-catalyzed cross-coupling reactions of heterocyclic chlorides with aryl and heteroaryl magnesium halides | |
Fukuzawa et al. | Copper (II) triflate as a double catalyst for the One-Pot click synthesis of 1, 4-disubstituted 1, 2, 3-triazoles from benzylic acetates | |
CN103214328A (en) | Synthesis method for alpha-bromo-aromatic ketone compounds | |
Thaler et al. | A novel synthetic approach towards chiral quinap via diastereomeric sulfoxide intermediates | |
CN1253422C (en) | Process for preparing 2-(6'-methoxy-2'-naphthyl) allyl alcohol | |
CN1290839C (en) | Preparation method of 2-methyl-2-aryl-1,3-oxa amylcyclo compound | |
CN1266133C (en) | Process for preparing acetyl substituted nitrogen containing heterocyclic compound | |
Ma et al. | CuI/N, N-dimethylglycine-catalyzed cross-coupling reaction of vinyl halides with phenols and its application to the assembly of substituted benzofurans | |
Arvela et al. | Fast and easy halide exchange in aryl halides | |
CN111116285B (en) | Efficient preparation method of 1-aryl-4-butene compound | |
CN109678673B (en) | Synthetic method of aryl-substituted homoallyl alcohol | |
Stadler et al. | Diastereoselective friedel-crafts alkylation reactions employing chiral cation precursors with polar α-substituents | |
Nandi et al. | Microwave‐Assisted Condensation of Benzylic Alcohols and Alkynes Promoted by Zinc Halides: Concise Access to Alkenyl Halides |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
EE01 | Entry into force of recordation of patent licensing contract |
Assignee: Zhejiang Jianfeng Haizhou Pharmacy Co., Ltd. Assignor: Zhejiang University of Technology Contract fulfillment period: 2009.5.15 to 2014.5.14 contract change Contract record no.: 2009330001436 Denomination of invention: 1-aryl (group) - 1 - ethylenialkene and production thereof Granted publication date: 20080109 License type: Exclusive license Record date: 2009.6.17 |
|
LIC | Patent licence contract for exploitation submitted for record |
Free format text: EXCLUSIVE LICENSE; TIME LIMIT OF IMPLEMENTING CONTACT: 2009.5.15 TO 2014.5.14; CHANGE OF CONTRACT Name of requester: ZHEJIANG JIANFENG HAIZHOU PHARMACEUTICAL CO., LTD. Effective date: 20090617 |
|
C17 | Cessation of patent right | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20080109 Termination date: 20121118 |