CN101219986B - 3-氰基吲哚类化合物及其合成方法 - Google Patents
3-氰基吲哚类化合物及其合成方法 Download PDFInfo
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- CN101219986B CN101219986B CN2007100362924A CN200710036292A CN101219986B CN 101219986 B CN101219986 B CN 101219986B CN 2007100362924 A CN2007100362924 A CN 2007100362924A CN 200710036292 A CN200710036292 A CN 200710036292A CN 101219986 B CN101219986 B CN 101219986B
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- 238000010189 synthetic method Methods 0.000 title claims description 12
- 238000000034 method Methods 0.000 claims abstract description 53
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- 229910052740 iodine Inorganic materials 0.000 claims abstract description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 197
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical group Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 31
- -1 methoxyl group Chemical group 0.000 claims description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- HMNQNULAYXDEEQ-UHFFFAOYSA-N acetic acid;hydroxylamine Chemical compound ON.CC(O)=O HMNQNULAYXDEEQ-UHFFFAOYSA-N 0.000 claims description 3
- VGYYSIDKAKXZEE-UHFFFAOYSA-L hydroxylammonium sulfate Chemical compound O[NH3+].O[NH3+].[O-]S([O-])(=O)=O VGYYSIDKAKXZEE-UHFFFAOYSA-L 0.000 claims description 3
- 239000012467 final product Substances 0.000 claims 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 150000002443 hydroxylamines Chemical class 0.000 abstract 1
- OLNJUISKUQQNIM-UHFFFAOYSA-N indole-3-carbaldehyde Chemical class C1=CC=C2C(C=O)=CNC2=C1 OLNJUISKUQQNIM-UHFFFAOYSA-N 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 49
- 238000004809 thin layer chromatography Methods 0.000 description 49
- 238000002360 preparation method Methods 0.000 description 47
- 238000003756 stirring Methods 0.000 description 47
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 45
- 238000001035 drying Methods 0.000 description 44
- 238000001914 filtration Methods 0.000 description 44
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- 230000008034 disappearance Effects 0.000 description 37
- 238000012797 qualification Methods 0.000 description 37
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- 150000003254 radicals Chemical class 0.000 description 20
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 9
- 229940074386 skatole Drugs 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 6
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 239000003153 chemical reaction reagent Substances 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
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- RDSVSEFWZUWZHW-UHFFFAOYSA-N 7-bromo-1h-indole Chemical compound BrC1=CC=CC2=C1NC=C2 RDSVSEFWZUWZHW-UHFFFAOYSA-N 0.000 description 2
- OEVSYHNNZOKQFD-UHFFFAOYSA-N 7-chloro-1h-indole-3-carbonitrile Chemical class ClC1=CC=CC2=C1NC=C2C#N OEVSYHNNZOKQFD-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
- RNMNPUCOFMWLLO-UHFFFAOYSA-N 4-methyl-1h-indole-3-carbonitrile Chemical compound CC1=CC=CC2=C1C(C#N)=CN2 RNMNPUCOFMWLLO-UHFFFAOYSA-N 0.000 description 1
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- KQMMMHWMPSFPSP-UHFFFAOYSA-N 5-chloro-1h-indole-3-carbonitrile Chemical compound ClC1=CC=C2NC=C(C#N)C2=C1 KQMMMHWMPSFPSP-UHFFFAOYSA-N 0.000 description 1
- OGJRYRXFDXWPHG-UHFFFAOYSA-N 5-fluoro-1h-indole-3-carbonitrile Chemical class FC1=CC=C2NC=C(C#N)C2=C1 OGJRYRXFDXWPHG-UHFFFAOYSA-N 0.000 description 1
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- SRDVYVLUUTYYSA-UHFFFAOYSA-N 5-phenylmethoxy-1h-indole-3-carbonitrile Chemical compound C1=C2C(C#N)=CNC2=CC=C1OCC1=CC=CC=C1 SRDVYVLUUTYYSA-UHFFFAOYSA-N 0.000 description 1
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- WAOJSSDVYZDEFM-UHFFFAOYSA-N 7-phenylmethoxy-1h-indole-3-carbonitrile Chemical compound C1=CC=C2C(C#N)=CNC2=C1OCC1=CC=CC=C1 WAOJSSDVYZDEFM-UHFFFAOYSA-N 0.000 description 1
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
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- Indole Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2007100362924A CN101219986B (zh) | 2007-01-09 | 2007-01-09 | 3-氰基吲哚类化合物及其合成方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2007100362924A CN101219986B (zh) | 2007-01-09 | 2007-01-09 | 3-氰基吲哚类化合物及其合成方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101219986A CN101219986A (zh) | 2008-07-16 |
| CN101219986B true CN101219986B (zh) | 2011-08-10 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN2007100362924A Active CN101219986B (zh) | 2007-01-09 | 2007-01-09 | 3-氰基吲哚类化合物及其合成方法 |
Country Status (1)
| Country | Link |
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| CN (1) | CN101219986B (en28) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102718694B (zh) * | 2012-06-27 | 2014-04-02 | 上海大学 | 3-氰基取代吲哚化合物及其合成方法 |
| CN102816104B (zh) * | 2012-08-30 | 2014-05-21 | 浙江大学 | 一种3-氰基吲哚类化合物的合成方法 |
| CN104610127B (zh) * | 2015-01-23 | 2017-04-05 | 常州大学 | 一种n‑烷基‑2‑芳基‑吲哚‑3‑醛的合成方法 |
-
2007
- 2007-01-09 CN CN2007100362924A patent/CN101219986B/zh active Active
Non-Patent Citations (1)
| Title |
|---|
| Jih Ru Hwu,et al.Sodium Bis(trimethylsilyl)amide in the Oxidative Conversion of Aldehydes to Nitriles.《European Journal of Organic Chemistry》.2006,第2006卷(第11期),2513-2516. * |
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| Publication number | Publication date |
|---|---|
| CN101219986A (zh) | 2008-07-16 |
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