Claims
- 1. A 2-substituted-2-cyclopentenone compound represented by the following formula (I): ##STR865## wherein R.sup.1 stands for a substituted or unsubstituted monocyclic or bicyclic heterocyclic group having 1 to 9 carbon atoms and having at least one element selected from the group consisting of nitrogen, oxygen and sulfur, or any combined group thereof; said substituent being selected from the group consisting of (i) a halogen atom; (ii) an oxo group; (iii) a cyano group; (iv) a nitro group; (v) --COOR.sup.61, wherein R.sup.61 stands for a hydrogen atom; one equivalent of a cation; a residue of a saccharide; or an aliphatic hydrocarbon group having 1 to 10 carbon atoms which may be substituted with a halogen atom, an oxo group, a hydroxyl group, a tri(C.sub.1 -C.sub.7) hydrocarbon silyloxy group, an acyloxy group having 2 to 7 carbon atoms, an alkoxycarbonyloxy group having 2 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group having 4 to 10 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms; (vi) --OR.sup.71, wherein R.sup.71 stands for a hydrogen atom; an acyl group having 2 to 7 carbon atoms; an alkoxycarbonyl group having 2 to 5 carbon atoms; a tri(C.sub.1 -C.sub.7) hydrocarbon silyl group; a group capable of forming an acetal bond together with the oxygen atom bonded to the R.sup.71 ; an aliphatic hydrocarbon group having 1 to 10 carbon atoms or an alicyclic hydrocarbon group having 4 to 10 carbon atoms which may be substituted with a halogen atom, an oxo group, a hydroxyl group, a carboxyl group, a tri(C.sub.1 -C.sub.7) hydrocarbon silyloxy group; an acyloxy group having 7 to 7 carbon atoms, an alkoxycarbonylxoy group having 2 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkoxycarbonyl group having 2 to 5 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms; or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with a halogen atom, a hydroxyl group, a nitro group, a tri(C.sub.1 -C.sub.7)hydrocarbon silyloxy group, an alkoxy group having 1 to 4 carbon atoms, an acyloxy group having 2 to 7 carbon atoms, an alkoxycarbonyloxy group having 2 to 5 carbon atoms, an acyl group having 2 to 7 carbon atoms, a carboxyl group, an alkoxycarbonyl group having 2 to 5 carbon atoms or an alkyl group having 1 to 4 carbon atoms; (vii) --CONR.sup.81 R.sup.810, wherein R.sup.81 and R.sup.810, which may be the same or different from each other, stand for a hydrogen atom; an aliphatic hydrocarbon group having 1 to 10 carbon atoms or an alicyclic hydrocarbon group having 4 to 10 carbon atoms which may be substituted with a halogen atom, an oxo group, a hydroxyl group, a tri(C.sub.1 -C.sub.7)hydrocarbon silyloxy group, an acyloxy group having 2 to 7 carbon atoms, an alkoxycarbvonyloxy group having 2 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms; an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with a halogen atom, a hydroxyl group, a nitro group, a tri-(C.sub.1 -C.sub. 7) hydrocarbon silyloxy group, an acyloxy group having 2 to 7 carbon atoms, an alkoxycarbonylxoy group having 2 to 5carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an acyl group having 2 to 7 carbon atoms, a carboxyl group, an alkoxycarbonyl group having 2 to 5 carbon atoms or an alkyl group having 1 to 4 carbon atoms; or a group wherein R.sup.81 and R.sup.810 are combined with each other to form a five- or six-membered ring; (vii) --NR.sup.91 R.sup.910, wherein R.sup.91 and R.sup.910, which may be the same of different from each other, stand for a hydrogen atom; an aliphatic hydrocarbon group having 1 to 10 carbon atoms or an alicyclic hydrocarbon group having 4 to 10 carbon atoms which may be substituted with a halogen atom, an oxo group, a hydroxyl group, a tri(C.sub.1 -C.sub.7) hydrocarbon silyloxy group, an acyloxy group having 2 to 7 carbon atoms, an alkoxycarbonyloxy group having 2 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms; an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with a halogen atom, a hydroxy group, a nitro group, a tri(C.sub.1 -C.sub.7)hydrocarbon silyloxy group, an acyloxy group having 2 to 7 carbon atoms, an alkoxycarbonylkoxy group having 2 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms; or a group wherein R.sup.91 and R.sup.910 are combined with each other to form a five- or six-membered ring; (ix) an aliphatic hydrocarbon group having 1 to 10 carbon atoms; (x) an alicyclic hydrocarbon group having 4 to 10 carbon atoms; (xi) an aromatic hydrocarbon group having 6 to 10 carbon atoms; and (xii) a heterocyclic group having 1 to 9 carbon atoms;
- R.sup.2 stands for a substituted or unsubstituted (i) aliphatic hydrocarbon group having 1 to 10 carbon atoms, (ii) alicyclic hydrocarbon group having 4 to 10 carbon atoms, (iii) aromatic hydrocarbon group having 6 to 10 carbon atoms or (iv) heterocyclic group having 1 to 9 carbon atoms; wherein the substituent for R.sup.2 is defined in the same way as the substituent for R.sup.1, provided that the substituent --COOR.sup.61 in the definition of R.sup.1 is --COOR.sup.62 where R.sup.62 is defined in the same way as R.sup.61 except that R.sup.62 further stands for an aliphatic hydrocarbon having 1 to 10 carbon atoms substituted with a nitro group, (b) the substituent --OR.sup.71 in the definition or R.sup.1 is OR.sup.72 where R.sup.72 is defined in the same way as R.sup.71 except that R.sup.72 does not represent an aromatic hydrocarbon group having 6 to 10 carbon atoms which is substituted with an alkoxy group having 1 to 4 carbon atoms or an acyloxy group having 2 to 7 carbon atoms, (c) the substituent --CONR.sup.81 R.sup.810 in the definition of R.sup.1 is --CONR.sup.82 R.sup.820 where R.sup.82 and R.sup.820 are defined in the same way as R.sup.81 and R.sup.810, respectively, (d) the substituent --NR.sup.91 R.sup.910 in the definition of R.sup.1 is --NR.sup.92 R.sup.920 independently further stand for an aromatic hydrocarbon group having 6 to 10 carbon atoms which is substituted with an acyl group having 2 to 7 carbon atoms, a carboxyl group, or an alkoxycarbonyl group having 2 to 5 carbon atoms, and (e) R.sup.2 further may stand for --SR.sup.76, wherein R.sup.76 stands for an aliphatic hydrocarbon group having 1 to 10 carbon atoms or an alicyclic hydrocarbon group having 4 to 10 carbon atoms which may be substituted with a halogen atom, an oxo group, a hydroxyl group, a carboxyl group, a tri(C.sub.1 -C.sub.7) hydrocarbon silyloxy group, an acyloxy group having 2 to 7 carbon atoms, an alkoxycarbonylxoy group having 2 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylcarbonyl group having 2 to 5 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms; an aromatic hydrocarbon having 6 to 10 carbon atoms which may be substituted with a halogen atom, a hydroxyl group, a tri(C.sub.1 -C.sub.7)hydrocarbon silyloxy group, a nitro group, an acyloxy group having 2 to 7 carbon atoms, an alkoxycarbonyloxy group having 2 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an acyl group having 2 to 7 carbon atoms, a carboxyl group, an alkoxycarbonyl group having 2 to 5 carbon atoms or an alkyl group having 1 to 4 carbon atoms; p1 R.sup.3 stands for a hydrogen atom or a substituted or unsubstituted (i) aliphatic hydrocarbon group having 1 to 10 carbon atoms, (ii) alicyclic hydrocarbon group having 4 to 10 carbon atoms or (iii) aromatic hydrocarbon group having 6 to 10 carbon atoms; wherein the substituent for R.sup.3 is defined in the same way as the substituent for R.sup.1, provide that (a) the substituent --COOR.sup.61 in the definition of R.sup.1 is --COOR.sup.63 where R.sup.63 is defined in the same way as R.sup.61 except that R.sup.63 further stands for an aliphatic hydrocarbon group having 1 to 10 carbon atoms substituted with a nitro group, (b) the substituent --OR.sup.71 in the definition of R.sup.1 is --OR.sup.73 where R.sup.73 is defined in the same way as R.sup.71, (c) the substituent --CONR.sup.81 R.sup.810 in the definition of R.sup.1 is --CONR.sup.83 R.sup.830 where R.sup.83 and R.sup.830 are defined in the same way as R.sup.81 and R.sup.810, respectively, and (d) the substituent --NR.sup.91 R.sup.910 is --NR.sup.93 R.sup.930 where R.sup.93 and R.sup.930 are defined in the same way as R.sup.91 and R.sup.910, respectively, except that R.sup.93 and R.sup.930 independently further stand for an aromatic hydrocarbon group having 6 to 10 carbon atoms which is substituted with an acyl group having 2 to 7 carbon atoms, a carboxyl group, or an alkoxycarbonyl group having 2 to 5 carbon atoms;
- X stands for a hydrogen atom or --OR.sup.4, wherein R.sup.4 stands for a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an acyl group having 2 to 7 carbon atoms, an alkoxycarbonyl group having 2 to 5 carbon atoms, a tri(C.sub.1 -C.sub.7) hydrocarbon silyl group or a group capable of forming an acetal bond together with the oxygen atom attached to the R.sup.4, provided that X is absent when R.sup.3 is bonded to the carbon atom bonding thereto through a double bond;
- R.sup.5 stands for a hydrogen atom, or a substituted or unsubstituted (i) aliphatic hydrocarbon group having 1 to 10 carbon atoms or (ii) an alicyclic hydrocarbon group having 4 to 10 carbon atoms; wherein the substituent for R.sup.5 is defined in the same way as the substituent for R.sup.1, provided that (a) the substituent --COOR.sup.61 in the definition of R.sup.1 is --COOR.sup.65 where R.sup.65 is defined in the same way as R.sup.61 except that R.sup.65 further stands for an aliphatic hydrocarbon group having 1 to 10 carbon atoms substituted with a nitro group, (b) the substituent --OR.sup.71 in the definition of R.sup.1 is --OR.sup.75 where R.sup.75 is defined in the same way as R.sup.71, (c) the substituent --CONR.sup.81 R.sup.810 in the definition of R.sup.1 is --CONR.sup.85 R.sup.850 where R.sup.85 and R.sup.850 are defined in the same way as R.sup.81 and R.sup.810, respectively, and (d) the substituent --NR.sup.91 R.sup.910 in the definition of R.sup.1 is --NR.sup.95 R.sup.950 where R.sup.95 and R.sup.950 are defined in the same way as R.sup.91 and R.sup.910, respectively, except that R.sup.95 and R.sup.950 independently further stand for an aromatic hydrocarbon group having 6 to 10 carbon atoms which is substituted with an acyl group having 2 to 7 carbon atoms, a carboxyl group, or an alkoxycarbonyl group having 2 to 5 carbon atoms;
- B stands for a hydrogen atom where A stands for a hydrogen atom, a hydroxyl group, an acyloxy group having 2 to 7 carbon atoms, an alkoxycarbonyloxy group having 2 to 5 carbon atoms, a sulfonyloxy group having 1 to 7 carbon atoms or ##STR866## or A and B are combined with each other to form a bond; m and n, which may be the same or different from each other, stand for 0, 1 or 2.
- 2. A 2-substituted-2-cyclopentenone compound according to claim 1, which is represented by the following formula (I.sub.A -A): ##STR867## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.5, X and n are as defined in claim 1 and represents that the substituent attached to the double bond is in an E-configuration or a Z-configuration or a mixture thereof in any proportion.
- 3. A 2-substituted-2-cyclopentenone compound according to claim 1, which is represented by the following formula (I.sub.A -B): ##STR868## wherein A.sup.A1 stands for a hydrogen atom, a hydroxyl group, an acyloxy group having 2 to 7 carbon atoms, an alkoxycarbonyloxy group having 2 to 5 carbon atoms, a sulfonyloxy group having 1 to 7 carbon atoms or ##STR869## and R.sup.1, R.sup.2, R.sup.3, R.sup.5, X, m and n are as defined in claim 1.
- 4. A 2-substituted-2-cyclopentenone compound according to claim 1 or 2, which is represented by the following formula (I.sub.A -A-2): ##STR870## wherein R.sup.1, R.sup.2, R.sup.4, R.sup.5, and n are as defined in claim 1; and represents that the substituent attached to the double bond is in an E-configuration or a Z-configuration or a mixture thereof in any proportion; and
- R.sub.30 stands for a hydrogen atom or a substituted or unsubstituted (i) aliphatic hydrocarbon group having 1 to 10 carbon atoms, (ii) alicyclic hydrocarbon group having 4 to 10 carbon atoms or (iii) aromatic hydrocarbon group having 6 to 10 carbon atoms.
- 5. A 2-substituted-2-cyclopentenone compound according to claim 1 or 2, which is represented by the following formula (I.sub.A -A-3): ##STR871## wherein R.sup.1, R.sup.2, R.sup.5, and n are as defined in claim 1 and represents that the substituent attached to the double bond is in an E-configuration or a Z-configuration or a mixture thereof in any proportion; and
- R.sup.31 and R.sup.32 which may be the same of different from each other stand for a hydrogen atom or a substituted or unsubstituted (i) aliphatic hydrocarbon group having 1 to 9 carbon atoms (ii) alicyclic hydrocarbon group having 4 to 10 carbon atoms or (iii) aromatic hydrocarbon group having 6 to 10 carbon atoms, or a group wherein the R.sup.31 and R.sup.32 are combined with each other to form an alicyclic hydrocarbon group having a four to ten-membered ring.
- 6. A 2-substituted-2-cyclopentenone compound according to claim 1 or 3, which is represented by the following formula (I.sub.A -B-2): ##STR872## wherein R.sup.1, R.sup.2, R.sup.4, R.sup.5 and n are as defined in claim 1;
- R.sup.30 stands for a hydrogen atom or a substituted or unsubstituted (i) aliphatic hydrocarbon group having 1 to 10 carbon atoms, (ii) alicyclic hydrocarbon group having 4 to 10 carbon atoms or (iii) aromatic hydrocarbon group having 6 to 10 carbon atoms; and
- A.sup.A2 stands for a hydrogen atom, a hydroxyl group, an acyloxy group having 2 to 7 carbon atoms or an alkoxycarbonyloxy group having 2 to 5 carbon atoms.
- 7. A 2-substituted-2-cyclopentenone compound according to claim 1, 2 or 4, which is represented by the following formula (I.sub.A0 -A-2): ##STR873## wherein R.sup.1, R.sup.2, R.sup.4, and n are as defined in claim 1 and represents that the substituent attached to the double bond is in an E-configuration or a Z-configuration or a mixture thereof in any proportion; and
- R.sup.33 stands for a substituted or unsubstituted (i) aliphatic hydrocarbon group having 1 to 10 carbon atoms, (ii) alicyclic hydrocarbon group having 4 to 10 carbon atoms or (iii) aromatic hydrocarbon group having 6 to 10 carbon atoms.
- 8. A 2-substituted-2-cyclopentenone compound according to claim 1, 2 or 5 which is represented by the following formula (I.sub.AO -A-3): ##STR874## wherein R.sup.1, R.sup.2, and n are as defined in claim 1; and R.sup.31 and R.sup.32 which may be the same of different from each other stand for a hydrogen atom or a substituted or unsubstituted (i) aliphatic hydrocarbon group having 1 to 9 carbon atoms or (ii) alicyclic hydrocarbon group having 4 to 10 carbon atoms or a group wherein the R.sup.31 and R.sup.32 are combined with each other to form an alicyclic hydrocarbon group having a four to ten-membered ring.
- and represents that the substituent attached to the double bond is in the E-configuration or a Z-configuration or a mixture thereof in an proportion.
- 9. A 2-substituted-2-cyclopentenone compound according to claim 1, 3 or 6 which is represented by the following formula ##STR875## wherein R.sup.1, R.sup.2, R.sup.4 and n are as defined in claim 1, R.sup.33 stands for a substituted or unsubstituted (i) aliphatic hydrocarbon group having 1 to 10 carbon atoms, (ii) alicyclic hydrocarbon group having 4 to 10 carbon atoms or (iii) aromatic hydrocarbon group having 6 to 10 carbon atoms; and
- R.sup.aO stands for a hydrogen atom, an acyl group having 2 to 7 carbon atoms or an alkoxycarbonyl group having 2 to 5 carbon atoms.
Priority Claims (1)
Number |
Date |
Country |
Kind |
1-272296 |
Oct 1989 |
JPX |
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Parent Case Info
This is a continuation of application Ser. No. 07/690,889, filed Jun. 19, 1991, now abandoned.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
5116869 |
Sugiura |
May 1992 |
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Foreign Referenced Citations (3)
Number |
Date |
Country |
0131441 |
Jan 1985 |
EPX |
2357542 |
Feb 1978 |
FRX |
58-109468 |
Jun 1983 |
JPX |
Continuations (1)
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Number |
Date |
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Parent |
690889 |
Jun 1991 |
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