CN105001130A - 一种3-芳基-2-环戊烯-1-酮化合物的合成方法 - Google Patents
一种3-芳基-2-环戊烯-1-酮化合物的合成方法 Download PDFInfo
- Publication number
- CN105001130A CN105001130A CN201510394243.2A CN201510394243A CN105001130A CN 105001130 A CN105001130 A CN 105001130A CN 201510394243 A CN201510394243 A CN 201510394243A CN 105001130 A CN105001130 A CN 105001130A
- Authority
- CN
- China
- Prior art keywords
- compound
- synthetic method
- formula
- reaction
- palladium
- 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
- 238000001308 synthesis method Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 27
- 239000003513 alkali Substances 0.000 claims abstract description 20
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 17
- 239000003960 organic solvent Substances 0.000 claims abstract description 16
- 239000012299 nitrogen atmosphere Substances 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 238000010189 synthetic method Methods 0.000 claims description 38
- -1 under catalyzer Substances 0.000 claims description 27
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 14
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000008367 deionised water Substances 0.000 claims description 6
- 229910021641 deionized water Inorganic materials 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 6
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 6
- 230000001105 regulatory effect Effects 0.000 claims description 6
- 238000010898 silica gel chromatography Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- KAIPKTYOBMEXRR-UHFFFAOYSA-N 1-butyl-3-methyl-2h-imidazole Chemical compound CCCCN1CN(C)C=C1 KAIPKTYOBMEXRR-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- DWOZNANUEDYIOF-UHFFFAOYSA-L bis(di-tert-butyl(4-dimethylaminophenyl)-phosphine)dichloropalladium(II) Substances Cl[Pd]Cl.CN(C)C1=CC=C(P(C(C)(C)C)C(C)(C)C)C=C1.CN(C)C1=CC=C(P(C(C)(C)C)C(C)(C)C)C=C1 DWOZNANUEDYIOF-UHFFFAOYSA-L 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical group [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 claims description 4
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 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 claims description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 3
- OLEYXOGJUOIDRR-UHFFFAOYSA-N butan-2-yl-ethyl-methoxy-methylazanium Chemical compound CCC(C)[N+](C)(CC)OC OLEYXOGJUOIDRR-UHFFFAOYSA-N 0.000 claims description 3
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 claims description 2
- OZIPZJIDBQUAJM-UHFFFAOYSA-N CC(C)(C)P(C(C)(C)C)C(C=C1)=CC=C1N(C)C.Cl.Cl Chemical compound CC(C)(C)P(C(C)(C)C)C(C=C1)=CC=C1N(C)C.Cl.Cl OZIPZJIDBQUAJM-UHFFFAOYSA-N 0.000 claims description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- PBDBXAQKXCXZCJ-UHFFFAOYSA-L palladium(2+);2,2,2-trifluoroacetate Chemical compound [Pd+2].[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F PBDBXAQKXCXZCJ-UHFFFAOYSA-L 0.000 claims description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 10
- 239000003054 catalyst Substances 0.000 abstract description 6
- 238000011160 research Methods 0.000 abstract description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 230000002195 synergetic effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentenylidene Natural products C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical class O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 125000001475 halogen functional group Chemical group 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000007341 Heck reaction Methods 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- KQAVUGAZLAPNJY-UHFFFAOYSA-N cyclopent-3-en-1-one Chemical class O=C1CC=CC1 KQAVUGAZLAPNJY-UHFFFAOYSA-N 0.000 description 2
- JYCYFUQFGXLZMB-UHFFFAOYSA-N cyclopentadeca-2,4,6,8,10,12,14-heptaen-1-one Chemical class O=C1C=CC=CC=CC=CC=CC=CC=C1 JYCYFUQFGXLZMB-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- JOHAQMAAWUPCOX-UHFFFAOYSA-N 1-iodobuta-1,3-diene Chemical class IC=CC=C JOHAQMAAWUPCOX-UHFFFAOYSA-N 0.000 description 1
- ZRNSSRODJSSVEJ-UHFFFAOYSA-N 2-methylpentacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(C)C ZRNSSRODJSSVEJ-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510394243.2A CN105001130B (zh) | 2015-07-07 | 2015-07-07 | 一种3-芳基-2-环戊烯-1-酮化合物的合成方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510394243.2A CN105001130B (zh) | 2015-07-07 | 2015-07-07 | 一种3-芳基-2-环戊烯-1-酮化合物的合成方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN105001130A true CN105001130A (zh) | 2015-10-28 |
CN105001130B CN105001130B (zh) | 2016-10-05 |
Family
ID=54374043
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201510394243.2A Expired - Fee Related CN105001130B (zh) | 2015-07-07 | 2015-07-07 | 一种3-芳基-2-环戊烯-1-酮化合物的合成方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN105001130B (zh) |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0643165A (ja) * | 1992-07-23 | 1994-02-18 | Lion Corp | 歯周疾患診断用抗原及び該抗原を利用した歯周疾患診断法 |
CN1155880A (zh) * | 1995-06-08 | 1997-07-30 | 弗门尼舍有限公司 | 制备不饱和环脂族酮的方法 |
CN1201027A (zh) * | 1997-06-04 | 1998-12-09 | 北京市化学工业研究院 | 合成2-戊基-3-丁氧环戊-2-烯酮的新工艺 |
US20040122007A1 (en) * | 2002-11-22 | 2004-06-24 | Yong-Jin Wu | 1-aryl-2-hydroxyethyl amides as potassium channel openers |
JP3882547B2 (ja) * | 2001-08-01 | 2007-02-21 | セイコーエプソン株式会社 | 4−フタロニトリル誘導体の製造方法 |
CN102199100A (zh) * | 2011-04-14 | 2011-09-28 | 淮海工学院 | 一种合成2,5-二取代氨基-1,4-苯醌类化合物的方法 |
CN103333093B (zh) * | 2013-06-17 | 2014-12-10 | 温州大学 | 一种1-芳硫基萘化合物的合成方法 |
-
2015
- 2015-07-07 CN CN201510394243.2A patent/CN105001130B/zh not_active Expired - Fee Related
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0643165A (ja) * | 1992-07-23 | 1994-02-18 | Lion Corp | 歯周疾患診断用抗原及び該抗原を利用した歯周疾患診断法 |
CN1155880A (zh) * | 1995-06-08 | 1997-07-30 | 弗门尼舍有限公司 | 制备不饱和环脂族酮的方法 |
CN1201027A (zh) * | 1997-06-04 | 1998-12-09 | 北京市化学工业研究院 | 合成2-戊基-3-丁氧环戊-2-烯酮的新工艺 |
JP3882547B2 (ja) * | 2001-08-01 | 2007-02-21 | セイコーエプソン株式会社 | 4−フタロニトリル誘導体の製造方法 |
US20040122007A1 (en) * | 2002-11-22 | 2004-06-24 | Yong-Jin Wu | 1-aryl-2-hydroxyethyl amides as potassium channel openers |
CN102199100A (zh) * | 2011-04-14 | 2011-09-28 | 淮海工学院 | 一种合成2,5-二取代氨基-1,4-苯醌类化合物的方法 |
CN103333093B (zh) * | 2013-06-17 | 2014-12-10 | 温州大学 | 一种1-芳硫基萘化合物的合成方法 |
Also Published As
Publication number | Publication date |
---|---|
CN105001130B (zh) | 2016-10-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Hughes et al. | Development of pharmaceutically relevant bio-based intermediates though aldol condensation and Claisen–Schmidt reactions of dihydrolevoglucosenone (Cyrene®) | |
Vijender et al. | Amberlist-15 as heterogeneous reusable catalyst for regioselective ring opening of epoxides with amines under mild conditions | |
Le et al. | Synthesis of a new urea derivative: a dual-functional organocatalyst for Knoevenagel condensation in water | |
CN105198841B (zh) | 一种药物中间体多取代呋喃类化合物的合成方法 | |
CN105732249A (zh) | 芳基醇类化合物及艾司西酞普兰合成方法 | |
Bauer et al. | Enantioselective addition of diethylzinc to aldehydes catalyzed by d-glucosamine derivatives: Highly pronounced effect of trifluoromethylsulfonamide | |
CN105175346B (zh) | 一种合成瑞舒伐他汀钙中间体的方法 | |
CN108864164B (zh) | 一种一级胺导向的2-炔基吲哚类化合物的合成方法 | |
CN105001130A (zh) | 一种3-芳基-2-环戊烯-1-酮化合物的合成方法 | |
CN104803912B (zh) | 一种医药中间体喹啉化合物的合成方法 | |
CN111978167B (zh) | 一种多取代环己-2-烯酮的一步合成方法 | |
Xu et al. | Highly enantioselective addition of methyl propiolate to aldehydes catalyzed by a titanium (IV) complex of a β-hydroxy amide | |
Loghmani-Khouzani et al. | A convenient synthesis of azines under solvent-free conditions using microwave irradiation | |
CN105001067A (zh) | 一种芳基取代环烯酮类化合物的合成方法 | |
CN105017189B (zh) | 一种稠合环酮类化合物的合成方法 | |
CN105481768A (zh) | 一种药物中间体二芳基酮化合物的合成方法 | |
Baharfar et al. | An efficient synthesis of substituted alkyl acrylates using α-keto amides | |
CN109096337B (zh) | 一种磷杂吲哚衍生物、苯并磷杂吲哚衍生物及其制备方法 | |
CN108623439A (zh) | 一种由芳基重氮盐和芳基磺酰肼制备联芳烃的方法 | |
Wang et al. | Electronic and steric effects of bis (oxazolinyl) pyridine ligands on asymmetric Diels–Alder reactions | |
CN110590641B (zh) | 一种3-羟基异吲哚-1-酮系列化合物的绿色制备方法 | |
CN111116510B (zh) | 一类2-取代亚甲基二氢苯并[d]噻唑类衍生物及其合成方法和应用 | |
CN104987318B (zh) | 一种萘乙烯基取代的环酮类化合物的合成方法 | |
CN106187965B (zh) | 一种药物中间体双环呋喃类化合物的合成方法 | |
CN105061391B (zh) | 一种芳炔基取代杂环酮类化合物的合成方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C41 | Transfer of patent application or patent right or utility model | ||
CB03 | Change of inventor or designer information |
Inventor after: Yu Hualong Inventor after: Wang Longyuan Inventor after: Ren Wei Inventor after: Zhou Changkai Inventor before: Zhang Linping |
|
COR | Change of bibliographic data | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20160901 Address after: 266000 Shandong city of Qingdao province Jiangsu City Road No. 16 Applicant after: Affiliated Hospital of University Of Qingdao Address before: 261418, No. 422, Lu Village, Yantai City, Shandong, Laizhou Applicant before: Zhang Linping |
|
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20161005 Termination date: 20170707 |