GB1038332A - 1,4-benzodioxan derivatives - Google Patents
1,4-benzodioxan derivativesInfo
- Publication number
- GB1038332A GB1038332A GB590163A GB590163A GB1038332A GB 1038332 A GB1038332 A GB 1038332A GB 590163 A GB590163 A GB 590163A GB 590163 A GB590163 A GB 590163A GB 1038332 A GB1038332 A GB 1038332A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzodioxan
- hydrogen
- methyl
- alkyl
- group
- 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.)
- Expired
Links
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical class C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 title abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 abstract 9
- 239000001257 hydrogen Substances 0.000 abstract 9
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- 125000005843 halogen group Chemical group 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 3
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 abstract 2
- ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- -1 amino compound Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 2
- OENICUBCLXKLJQ-UHFFFAOYSA-N ethyl 2,3-dibromopropanoate Chemical compound CCOC(=O)C(Br)CBr OENICUBCLXKLJQ-UHFFFAOYSA-N 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- PSTWEVWIDGVCNY-UHFFFAOYSA-N 2,3-dihydrobenzo[g][1,4]benzodioxine-3-carboxylic acid Chemical compound C1=CC=C2C=C(OC(C(=O)O)CO3)C3=CC2=C1 PSTWEVWIDGVCNY-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- JBVKWCMJQRCLHL-UHFFFAOYSA-N 2-amino-1-(2,3-dihydro-1,4-benzodioxin-3-yl)ethanol Chemical compound C1=CC=C2OC(C(O)CN)COC2=C1 JBVKWCMJQRCLHL-UHFFFAOYSA-N 0.000 abstract 1
- NJOHOHGFMQTANR-UHFFFAOYSA-N 2-bromo-1-(2,3-dihydro-1,4-benzodioxin-3-yl)ethanol Chemical compound C1=CC=C2OC(C(CBr)O)COC2=C1 NJOHOHGFMQTANR-UHFFFAOYSA-N 0.000 abstract 1
- YTANAAYEOKJUPV-UHFFFAOYSA-N 2-chloro-1-(2,3-dihydro-1,4-benzodioxin-3-yl)ethanol Chemical compound C1=CC=C2OC(C(CCl)O)COC2=C1 YTANAAYEOKJUPV-UHFFFAOYSA-N 0.000 abstract 1
- LVUZRMKBNBMKSP-UHFFFAOYSA-N 2-chloro-1-(2,3-dihydrobenzo[g][1,4]benzodioxin-3-yl)ethanol Chemical compound ClCC(O)C1COC2=C(O1)C=C1C=CC=CC1=C2 LVUZRMKBNBMKSP-UHFFFAOYSA-N 0.000 abstract 1
- BAALQSDAYJHANE-UHFFFAOYSA-N 2-chloro-1-(2,3-dihydrobenzo[g][1,4]benzodioxin-3-yl)ethanone Chemical compound ClCC(=O)C1COC2=C(O1)C=C1C=CC=CC1=C2 BAALQSDAYJHANE-UHFFFAOYSA-N 0.000 abstract 1
- MXFPTEVVVBVJKF-UHFFFAOYSA-N 2-diazo-1-(2,3-dihydrobenzo[g][1,4]benzodioxin-3-yl)ethanone Chemical compound [N+](=[N-])=CC(=O)C1COC2=C(O1)C=C1C=CC=CC1=C2 MXFPTEVVVBVJKF-UHFFFAOYSA-N 0.000 abstract 1
- 101100277337 Arabidopsis thaliana DDM1 gene Proteins 0.000 abstract 1
- QOKWUVJBPHAQMR-UHFFFAOYSA-N Cl.C(C)(C)(C)NCC(=O)C1COC2=C(O1)C=CC=C2 Chemical compound Cl.C(C)(C)(C)NCC(=O)C1COC2=C(O1)C=CC=C2 QOKWUVJBPHAQMR-UHFFFAOYSA-N 0.000 abstract 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001264 acyl cyanides Chemical class 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 101150113676 chr1 gene Proteins 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- GTVYMEJRCYKQDR-UHFFFAOYSA-N ethyl 2,3-dihydrobenzo[g][1,4]benzodioxine-3-carboxylate Chemical compound C1=CC=C2C=C(OC(C(=O)OCC)CO3)C3=CC2=C1 GTVYMEJRCYKQDR-UHFFFAOYSA-N 0.000 abstract 1
- 238000001640 fractional crystallisation Methods 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 150000004678 hydrides Chemical class 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- JRNGUTKWMSBIBF-UHFFFAOYSA-N naphthalene-2,3-diol Chemical compound C1=CC=C2C=C(O)C(O)=CC2=C1 JRNGUTKWMSBIBF-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB590163A GB1038332A (en) | 1963-02-13 | 1963-02-13 | 1,4-benzodioxan derivatives |
| CH149164A CH450450A (de) | 1963-02-13 | 1964-02-07 | Verfahren zur Herstellung von neuen 1,4-Benzodioxanderivaten |
| DE19641493850 DE1493850A1 (de) | 1963-02-13 | 1964-02-11 | Verfahren zur Herstellung von Benzodioxanderivaten |
| SE1702/64A SE313060B (enrdf_load_stackoverflow) | 1963-02-13 | 1964-02-12 | |
| AT122664A AT244339B (de) | 1963-02-13 | 1964-02-13 | Verfahren zur Herstellung von neuen 1, 4-Benzodioxanderivaten |
| AT796964A AT246737B (de) | 1963-02-13 | 1964-02-13 | Verfahren zur Herstellung von neuen 1,4-Benzodioxanderivaten |
| DK517164A DK107295C (da) | 1963-02-13 | 1964-02-13 | Fremgangsmåde til fremstilling af 1,4-benzodioksanderivater. |
| AT796764A AT246135B (de) | 1963-02-13 | 1964-02-13 | Verfahren zur Herstellung von neuen 1,4-Benzodioxanderivaten |
| NL6401243A NL6401243A (enrdf_load_stackoverflow) | 1963-02-13 | 1964-02-13 | |
| DK69764A DK107754C (da) | 1963-02-13 | 1964-02-13 | Fremgangsmåde til fremstilling af 1,4-benzodioksanderivater. |
| FR963699A FR1402887A (fr) | 1963-02-13 | 1964-02-13 | Procédé de préparation de dérivés de 1, 4-benzodioxane |
| BE643778A BE643778A (enrdf_load_stackoverflow) | 1963-02-13 | 1964-02-13 | |
| DK517264A DK107101C (da) | 1963-02-13 | 1964-02-13 | Fremgangsmåde til fremstilling af 1,4-benzodioksanderivater. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB590163A GB1038332A (en) | 1963-02-13 | 1963-02-13 | 1,4-benzodioxan derivatives |
| BE643778A BE643778A (enrdf_load_stackoverflow) | 1963-02-13 | 1964-02-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1038332A true GB1038332A (en) | 1966-08-10 |
Family
ID=25655689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB590163A Expired GB1038332A (en) | 1963-02-13 | 1963-02-13 | 1,4-benzodioxan derivatives |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE643778A (enrdf_load_stackoverflow) |
| CH (1) | CH450450A (enrdf_load_stackoverflow) |
| DE (1) | DE1493850A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1038332A (enrdf_load_stackoverflow) |
| NL (1) | NL6401243A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4212808A (en) * | 1979-03-09 | 1980-07-15 | Ciba-Geigy Corporation | 2-Oxiranyl-1,4-benzodioxans |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR207639A1 (es) * | 1973-12-26 | 1976-10-22 | Pfizer | Un procedimiento para preparar pirido (3,2-d)1,3-dioxin-6-epoxietanos y compuestos intermediarios desprovistos de actividad terapeutica |
-
1963
- 1963-02-13 GB GB590163A patent/GB1038332A/en not_active Expired
-
1964
- 1964-02-07 CH CH149164A patent/CH450450A/de unknown
- 1964-02-11 DE DE19641493850 patent/DE1493850A1/de active Pending
- 1964-02-13 BE BE643778A patent/BE643778A/xx unknown
- 1964-02-13 NL NL6401243A patent/NL6401243A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4212808A (en) * | 1979-03-09 | 1980-07-15 | Ciba-Geigy Corporation | 2-Oxiranyl-1,4-benzodioxans |
Also Published As
| Publication number | Publication date |
|---|---|
| BE643778A (enrdf_load_stackoverflow) | 1964-08-13 |
| DE1493850A1 (de) | 1969-07-24 |
| NL6401243A (enrdf_load_stackoverflow) | 1964-08-14 |
| CH450450A (de) | 1968-01-31 |
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