CN105985263A - 一种n,n-二取代氨基-丙二腈类化合物的合成方法 - Google Patents
一种n,n-二取代氨基-丙二腈类化合物的合成方法 Download PDFInfo
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- CN105985263A CN105985263A CN201510054946.0A CN201510054946A CN105985263A CN 105985263 A CN105985263 A CN 105985263A CN 201510054946 A CN201510054946 A CN 201510054946A CN 105985263 A CN105985263 A CN 105985263A
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- copper
- disubstituted amido
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- cyacetazid
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- 238000010189 synthetic method Methods 0.000 title claims abstract description 8
- GXDKXRIMUVUELI-UHFFFAOYSA-N 2-aminopropanedinitrile Chemical class N#CC(N)C#N GXDKXRIMUVUELI-UHFFFAOYSA-N 0.000 title abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052802 copper Inorganic materials 0.000 claims abstract description 14
- 239000010949 copper Substances 0.000 claims abstract description 14
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 claims abstract description 8
- -1 amino-substituted malononitrile Chemical class 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 claims description 2
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 2
- DANBQHLZCHUINA-UHFFFAOYSA-N [SiH4].N#CC#N Chemical compound [SiH4].N#CC#N DANBQHLZCHUINA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 claims description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 2
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 claims description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 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
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 claims 1
- 125000005956 isoquinolyl group Chemical group 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 6
- 239000011261 inert gas Substances 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-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
- 238000001514 detection method Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- ZEMNVPLWDUWKEG-UHFFFAOYSA-N 3,4-dihydro-1h-isoquinoline-2-carbaldehyde Chemical compound C1=CC=C2CN(C=O)CCC2=C1 ZEMNVPLWDUWKEG-UHFFFAOYSA-N 0.000 description 2
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003863 metallic catalyst Substances 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ZGZUKKMFYTUYHA-HNNXBMFYSA-N (2s)-2-amino-3-(4-phenylmethoxyphenyl)propane-1-thiol Chemical group C1=CC(C[C@@H](CS)N)=CC=C1OCC1=CC=CC=C1 ZGZUKKMFYTUYHA-HNNXBMFYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 231100000004 severe toxicity Toxicity 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Abstract
Description
Claims (5)
Priority Applications (1)
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CN201510054946.0A CN105985263B (zh) | 2015-02-03 | 2015-02-03 | 一种n,n-二取代氨基-丙二腈类化合物的合成方法 |
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CN201510054946.0A CN105985263B (zh) | 2015-02-03 | 2015-02-03 | 一种n,n-二取代氨基-丙二腈类化合物的合成方法 |
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Publication Number | Publication Date |
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CN105985263A true CN105985263A (zh) | 2016-10-05 |
CN105985263B CN105985263B (zh) | 2019-02-15 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114249724A (zh) * | 2020-09-25 | 2022-03-29 | 鲁南制药集团股份有限公司 | 一种唑吡坦中间体的制备方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3019261A (en) * | 1959-03-12 | 1962-01-30 | Du Pont | Nu-fluorinatedalkyl-amides of alkanoic acids and process of preparation |
DE1128431B (de) * | 1960-11-16 | 1962-04-26 | Bayer Ag | Verfahren zur Herstellung basisch substituierter Malonsaeuredinitrile |
DE10057055A1 (de) * | 2000-11-17 | 2002-05-23 | Bayer Ag | Verfahren zur Herstellung von aminosubstituierten Malonsäuredinitrilen |
-
2015
- 2015-02-03 CN CN201510054946.0A patent/CN105985263B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3019261A (en) * | 1959-03-12 | 1962-01-30 | Du Pont | Nu-fluorinatedalkyl-amides of alkanoic acids and process of preparation |
DE1128431B (de) * | 1960-11-16 | 1962-04-26 | Bayer Ag | Verfahren zur Herstellung basisch substituierter Malonsaeuredinitrile |
DE10057055A1 (de) * | 2000-11-17 | 2002-05-23 | Bayer Ag | Verfahren zur Herstellung von aminosubstituierten Malonsäuredinitrilen |
Non-Patent Citations (2)
Title |
---|
ALBERT PADWA等: "Synthetic Application of Cyanoaminosilanes as Azomethine Ylide", 《J. ORG. CHEM.》 * |
P. SARAVANAN等: "Cu(OTf)2 Catalyzed Trimethylsilyl Cyanide Addition to Carbonyl Compounds", 《TETRAHEDRON LETTERS》 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114249724A (zh) * | 2020-09-25 | 2022-03-29 | 鲁南制药集团股份有限公司 | 一种唑吡坦中间体的制备方法 |
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Effective date of registration: 20240118 Address after: 055550 Building C7, Fangda Science and Technology Park, Ningjin County, Xingtai City, Hebei Province Patentee after: Lanqimengda Pharmaceutical Technology (Ningjin) Co.,Ltd. Address before: 730000 Lanzhou University, 222 Tianshui South Road, Chengguan District, Lanzhou City, Gansu Province Patentee before: LANZHOU University |
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