GB1446343A - Cyclopenta-6-furan derivatives - Google Patents
Cyclopenta-6-furan derivativesInfo
- Publication number
- GB1446343A GB1446343A GB1420176A GB1420176A GB1446343A GB 1446343 A GB1446343 A GB 1446343A GB 1420176 A GB1420176 A GB 1420176A GB 1420176 A GB1420176 A GB 1420176A GB 1446343 A GB1446343 A GB 1446343A
- Authority
- GB
- United Kingdom
- Prior art keywords
- double bond
- hydrogen
- corresponding compound
- cyclopenta
- furan derivatives
- 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
- -1 3,4 - methylenedioxyphenyl Chemical group 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- XSDLSEOIVCVTQZ-UHFFFAOYSA-N 2h-cyclopenta[b]furan Chemical class C1=CC2=CCOC2=C1 XSDLSEOIVCVTQZ-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000000468 ketone group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 abstract 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 abstract 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 150000002240 furans Chemical class 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B63—SHIPS OR OTHER WATERBORNE VESSELS; RELATED EQUIPMENT
- B63B—SHIPS OR OTHER WATERBORNE VESSELS; EQUIPMENT FOR SHIPPING
- B63B2211/00—Applications
- B63B2211/02—Oceanography
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1446343 Cyclopenta(b)furan derivatives PFIZER Inc 13 July 1973 [13 July 1972] 14201/76 Divided out of 1446341 Heading C2C Novel cyclopenta(6)furan derivatives of the general Formula I wherein Ar is α- or #-furyl, -thienyl or -naphthyl, 3,4 - methylenedioxyphenyl, 3,4,5 - trimethoxyphenyl or biphenylyl, Z is a single or transdouble bond and n is 1-5, with the proviso that when Ar is substituted phenyl, biphenylyl or naphthyl, n is 1, are prepared (a) when Z is a double bond, by reacting an aldehyde of the Formula IV with wherein R<SP>1</SP> is a C 1 - 4 alkyl group, and (b) when Z is a single bond, by oxidizing the corresponding compound wherein the side-chain keto group is replaced by -CH(OH)-. Novel cyclopenta(b)furan derivatives of the general Formula II wherein R is hydrogen or C 1-4 alkyl and Q is hydrogen or p-biphenylylcarbonyl, are prepared (c) when Z is a double bond and R is hydrogen, by reducing the corresponding compound having a keto group instead of the -C(R)(OH)- group, (d) when Z is a double bond and R is C 1-4 alkyl, by treating the starting material of (c) with the appropriate lithium alkyl or Grignard reagent, (e) when Q is hydrogen and Z is a double bond, by treating the corresponding compound in which Q is p-biphenylylcarbonyl with K 2 CO 3 and (f) when Z is a single bond, by reduction of the corresponding compound in which Z is a double bond. Novel cyclopenta(b)furan derivatives of the general Formula III wherein THP is 2-tetrahydropyranyl and X is = O or (H, OH), are prepared (g) when X is =O, by reacting a compound II in which Q is hydrogen with 2,3-dihydropyran in the presence of an acid catalyst, (h) when X is (H, OH), by reacting the product of (g) with diisobutylaluminium hydride and (i) when Z is a single bond and X is = 0, by catalytically hydrogenating the corresponding compound in which Z is a double bond.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27122072A | 1972-07-13 | 1972-07-13 | |
| GB3121773A GB1446341A (en) | 1972-07-13 | 1973-07-13 | 15-substituted-omega-pentanorprostaglandins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1446343A true GB1446343A (en) | 1976-08-18 |
Family
ID=26260791
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1420176A Expired GB1446343A (en) | 1972-07-13 | 1973-07-13 | Cyclopenta-6-furan derivatives |
| GB1355676A Expired GB1446342A (en) | 1972-07-13 | 1973-07-13 | Substituted alkyl phosphonate diesters |
| GB1444976A Expired GB1446344A (en) | 1972-07-13 | 1973-07-13 | Bis-tetrahydropyranyl-ethers |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1355676A Expired GB1446342A (en) | 1972-07-13 | 1973-07-13 | Substituted alkyl phosphonate diesters |
| GB1444976A Expired GB1446344A (en) | 1972-07-13 | 1973-07-13 | Bis-tetrahydropyranyl-ethers |
Country Status (1)
| Country | Link |
|---|---|
| GB (3) | GB1446343A (en) |
-
1973
- 1973-07-13 GB GB1420176A patent/GB1446343A/en not_active Expired
- 1973-07-13 GB GB1355676A patent/GB1446342A/en not_active Expired
- 1973-07-13 GB GB1444976A patent/GB1446344A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1446344A (en) | 1976-08-18 |
| GB1446342A (en) | 1976-08-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |