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【结 构 式】 
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【分子编号】33891 【品名】Methyl ethyl ketone; 2-Butanone 【CA登记号】78-93-3 |
【 分 子 式 】C4H8O 【 分 子 量 】72.10692 【元素组成】C 66.63% H 11.18% O 22.19% |
合成路线1
该中间体在本合成路线中的序号：(A)Compound can be prepared by several different ways: 1) By condensation of cyclohexylidenebis(4-hydroxyphenyl) (I) with 2-butanone (A) and CHCl3 by means of NaOH or KOH at 50-150 C. 2) By alkylation of cyclohexylidenebis(4,1-phenyleneoxy)bis(2-butanoic acid) diethyl ester (III) with NaH and methyl iodide in DMF to give the ester (IV), which is then hydrolyzed with K2CO3 in methanol. 3) By oxidation of cyclohexylidenebis(4,1-phenyleneoxy)bis(2-oxo-3-methyl-3-pentyl) (II) with sodium hypobromite or potassium hypochlorite in dioxane - water.
| 【1】 Nakamura, Y.; et al.; Phenoxy carboxylic acid derivative. BE 0748970; FR 2042333; US 3716583 . |
| 【2】 Yoshitake, A.; et al.; JP 7354047 . |
| 【3】 Nakamura, Y.; et al.; JP 7248378 . |
| 【4】 Roberts, P.J.; Castaner, J.; S-8527. Drugs Fut 1977, 2, 5, 328. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 33891 | Methyl ethyl ketone; 2-Butanone | 78-93-3 | C4H8O | 详情 | 详情 |
| (I) | 33890 | 4-[1-(4-hydroxyphenyl)cyclohexyl]phenol | 843-55-0 | C18H20O2 | 详情 | 详情 |
| (II) | 33892 | 3-(4-[1-[4-(1-ethyl-1-methyl-2-oxopropoxy)phenyl]cyclohexyl]phenoxy)-3-methyl-2-pentanone | C30H40O4 | 详情 | 详情 | |
| (III) | 33893 | ethyl 2-[4-(1-[4-[1-(ethoxycarbonyl)propoxy]phenyl]cyclohexyl)phenoxy]butanoate | C30H40O6 | 详情 | 详情 | |
| (IV) | 33894 | ethyl 2-[4-(1-[4-[1-(ethoxycarbonyl)-1-methylpropoxy]phenyl]cyclohexyl)phenoxy]-2-methylbutanoate | C32H44O6 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IV)Synthesis of undecenoic ester intermediate (XXI): The reaction of 2,2-dimethylpropane-1,3-diol (I) with benzaldehyde, TsOH and DIBAL gives the monobenzyl ether (II), which is oxidized with SO3/pyridine in dichloromethane, yielding the propionaldehyde (III). The condensation of (III) with butanone (IV) by means of LDA and TFAA affords the heptenone (V), which is epoxidated with H2O2 and NaOH in aq. methanol to provide the racemic epoxide (rac)-(VI). The reaction of ketone (VI) with O-methylhydroxylamine and NaOAc in methanol gives the corresponding oxime (rac)-(VII), which is treated with CuCN and Me-Li in ethyl ether to yield the beta-hydroxy oxime (rac)-(VIII). The treatment of (VIII) with H2 and Raney-Ni in acetone/THF affords the corresponding beta-hydroxy ketone (rac)-(IX), which is allylated with allyl bromide (X) and LHMDS in the presence of 1,3-dimethylperhydropyrimidin-2-one to give the beta-hydroxynonen-5-one (rac)-(XI). The reduction of (XI) with Me4NBH(OAc)3 and HOAc in acetonitrile yields the diol (rac)-(XII), which is protected with 2-methoxypropene (XIII) and TsOH, affording the 1,3-dioxane (rac)-(XIV). The reaction of (XIV) with Li in liquid ammonia, tert-butanol and THF provides the debenzylated primary alcohol (rac)-(XV), which is oxidized with tetrapropylammonium perrhuthenate in dichloromethane, giving the corresponding aldehyde (rac)-(XVI).
| 【1】 Sawada, D.; et al.; Enantioselective total synthesis of epothilones A and B using multifunctional asymmetric catalysis. J Am Chem Soc 2000, 122, 43, 10521. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 12641 | Neopentyl glycol; 2,2-Dimethyl-1,3-propanediol | 126-30-7 | C5H12O2 | 详情 | 详情 |
| (II) | 44529 | 3-(benzyloxy)-2,2-dimethyl-1-propanol | C12H18O2 | 详情 | 详情 | |
| (III) | 44504 | 3-(benzyloxy)-2,2-dimethylpropanal | C12H16O2 | 详情 | 详情 | |
| (IV) | 33891 | Methyl ethyl ketone; 2-Butanone | 78-93-3 | C4H8O | 详情 | 详情 |
| (V) | 44505 | (E)-7-(benzyloxy)-6,6-dimethyl-4-hepten-3-one | C16H22O2 | 详情 | 详情 | |
| (VI) | 44506 | 1-[3-[2-(benzyloxy)-1,1-dimethylethyl]-2-oxiranyl]-1-propanone | C16H22O3 | 详情 | 详情 | |
| (VII) | 44507 | 1-[3-[2-(benzyloxy)-1,1-dimethylethyl]-2-oxiranyl]-1-propanone O-methyloxime | C17H25NO3 | 详情 | 详情 | |
| (VIII) | 44508 | (4R,5R)-7-(benzyloxy)-5-hydroxy-4,6,6-trimethyl-3-heptanone O-methyloxime | C18H29NO3 | 详情 | 详情 | |
| (IX) | 44509 | (4S,5R)-7-(benzyloxy)-5-hydroxy-4,6,6-trimethyl-3-heptanone | C17H26O3 | 详情 | 详情 | |
| (X) | 11463 | 3-Bromo-1-propene; 3-Bromopropene；allyl bromide | 106-95-6 | C3H5Br | 详情 | 详情 |
| (XI) | 44510 | (4S,6S,7R)-9-(benzyloxy)-7-hydroxy-4,6,8,8-tetramethyl-1-nonen-5-one | C20H30O3 | 详情 | 详情 | |
| (XII) | 44511 | (3R,4R,5S,6S)-1-(benzyloxy)-2,2,4,6-tetramethyl-8-nonene-3,5-diol | C20H32O3 | 详情 | 详情 | |
| (XIII) | 17354 | isopropenyl methyl ether; 2-methoxy-1-propene | 116-11-0 | C4H8O | 详情 | 详情 |
| (XIV) | 44512 | benzyl 2-methyl-2-[(4R,5S,6S)-2,2,5-trimethyl-6-[(1S)-1-methyl-3-butenyl]-1,3-dioxan-4-yl]propyl ether; (4R,5S,6S)-4-[2-(benzyloxy)-1,1-dimethylethyl]-2,2,5-trimethyl-6-[(1S)-1-methyl-3-butenyl]-1,3-dioxane | C23H36O3 | 详情 | 详情 | |
| (XV) | 44513 | 2-methyl-2-[(4R,5S,6S)-2,2,5-trimethyl-6-[(1S)-1-methyl-3-butenyl]-1,3-dioxan-4-yl]-1-propanol | C16H30O3 | 详情 | 详情 | |
| (XVI) | 44514 | 2-methyl-2-[(4R,5S,6S)-2,2,5-trimethyl-6-[(1S)-1-methyl-3-butenyl]-1,3-dioxan-4-yl]propanal | C16H28O3 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(IV)The reaction of 2,2-dimethylpropane-1,3-diol (I) with benzaldehyde, Ts-OH and DIBAL gives the monobenzyl ether (II), which is oxidized with SO3/pyridine in dichloromethane, yielding the propionaldehyde (III). The condensation of (III) with butanone (IV) by means of LDA and TFAA affords the heptenone (V), which is epoxidated with H2O2 and NaOH in aq. methanol to provide the racemic epoxide (rac)-(VI). The reaction of ketone (VI) with O-methylhydroxylamine and NaOAc in methanol gives the corresponding oxime (rac)-(VII), which is treated with CuCN and MeLi in ethyl ether to yield the beta-hydroxy oxime (rac)-(VIII). The treatment of (VIII) with H2 and Raney-Ni in acetone/THF affords the corresponding beta-hydroxy ketone (rac)-(IX), which is allylated with allyl bromide (X) and LHMDS in the presence of 1,3-dimethylperhydropyrimidin-2-one to give the beta-hydroxynonen-5-one (rac)-(XI). The reduction of (XI) with Me4NBH(OAc)3 and HOAc in acetonitrile yields the diol (rac)-(XII), which is protected with 2-methoxypropene (XIII) and Ts-OH, affording the 1,3-dioxane (rac)-(XIV). The reaction of (XIV) with Li in liquid ammonia, tert-butanol and THF provides the debenzylated primary alcohol (rac)-(XV), which is oxidized with tetrapropylammonium perrhuthenate in dichloromethane, giving the corresponding aldehyde (rac)-(XVI).
| 【1】 Sawada, D.; et al.; Enantioselective total synthesis of epothilones A and B using multifunctional asymmetric catalysis. J Am Chem Soc 2000, 122, 43, 10521. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 12641 | Neopentyl glycol; 2,2-Dimethyl-1,3-propanediol | 126-30-7 | C5H12O2 | 详情 | 详情 |
| (II) | 44529 | 3-(benzyloxy)-2,2-dimethyl-1-propanol | C12H18O2 | 详情 | 详情 | |
| (III) | 44504 | 3-(benzyloxy)-2,2-dimethylpropanal | C12H16O2 | 详情 | 详情 | |
| (IV) | 33891 | Methyl ethyl ketone; 2-Butanone | 78-93-3 | C4H8O | 详情 | 详情 |
| (V) | 44505 | (E)-7-(benzyloxy)-6,6-dimethyl-4-hepten-3-one | C16H22O2 | 详情 | 详情 | |
| (VI) | 44506 | 1-[3-[2-(benzyloxy)-1,1-dimethylethyl]-2-oxiranyl]-1-propanone | C16H22O3 | 详情 | 详情 | |
| (VII) | 44507 | 1-[3-[2-(benzyloxy)-1,1-dimethylethyl]-2-oxiranyl]-1-propanone O-methyloxime | C17H25NO3 | 详情 | 详情 | |
| (VIII) | 44508 | (4R,5R)-7-(benzyloxy)-5-hydroxy-4,6,6-trimethyl-3-heptanone O-methyloxime | C18H29NO3 | 详情 | 详情 | |
| (IX) | 44509 | (4S,5R)-7-(benzyloxy)-5-hydroxy-4,6,6-trimethyl-3-heptanone | C17H26O3 | 详情 | 详情 | |
| (X) | 11463 | 3-Bromo-1-propene; 3-Bromopropene；allyl bromide | 106-95-6 | C3H5Br | 详情 | 详情 |
| (XI) | 44510 | (4S,6S,7R)-9-(benzyloxy)-7-hydroxy-4,6,8,8-tetramethyl-1-nonen-5-one | C20H30O3 | 详情 | 详情 | |
| (XII) | 44511 | (3R,4R,5S,6S)-1-(benzyloxy)-2,2,4,6-tetramethyl-8-nonene-3,5-diol | C20H32O3 | 详情 | 详情 | |
| (XIII) | 17354 | isopropenyl methyl ether; 2-methoxy-1-propene | 116-11-0 | C4H8O | 详情 | 详情 |
| (XIV) | 44512 | benzyl 2-methyl-2-[(4R,5S,6S)-2,2,5-trimethyl-6-[(1S)-1-methyl-3-butenyl]-1,3-dioxan-4-yl]propyl ether; (4R,5S,6S)-4-[2-(benzyloxy)-1,1-dimethylethyl]-2,2,5-trimethyl-6-[(1S)-1-methyl-3-butenyl]-1,3-dioxane | C23H36O3 | 详情 | 详情 | |
| (XV) | 44513 | 2-methyl-2-[(4R,5S,6S)-2,2,5-trimethyl-6-[(1S)-1-methyl-3-butenyl]-1,3-dioxan-4-yl]-1-propanol | C16H30O3 | 详情 | 详情 | |
| (XVI) | 44514 | 2-methyl-2-[(4R,5S,6S)-2,2,5-trimethyl-6-[(1S)-1-methyl-3-butenyl]-1,3-dioxan-4-yl]propanal | C16H28O3 | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(IV)The reaction of 2,2-dimethylpropane-1,3-diol (I) with benzaldehyde, Ts-OH and DIBAL gives the monobenzyl ether (II), which is oxidized with SO3/pyridine in dichloromethane, yielding the propionaldehyde (III). The condensation of (III) with butanone (IV) by means of LDA and TFAA affords the heptenone (V), which is epoxidated with H2O2 and NaOH in aq. methanol to provide the racemic epoxide (rac)-(VI). The reaction of ketone (VI) with O-methylhydroxylamine and NaOAc in methanol gives the corresponding oxime (rac)-(VII), which is treated with CuCN and MeLi in ethyl ether to yield the beta-hydroxy oxime (rac)-(VIII). The treatment of (VIII) with H2 and Raney-Ni in acetone/THF affords the corresponding beta-hydroxy ketone (rac)-(IX), which is allylated with allyl bromide (X) and LHMDS in the presence of 1,3-dimethylperhydropyrimidin-2-one to give the beta-hydroxynonen-5-one (rac)-(XI). The reduction of (XI) with Me4NBH(OAc)3 and HOAc in acetonitrile yields the diol (rac)-(XII), which is protected with 2-methoxypropene (XIII) and Ts-OH, affording the 1,3-dioxane (rac)-(XIV). The reaction of (XIV) with Li in liquid ammonia, tert-butanol and THF provides the debenzylated primary alcohol (rac)-(XV), which is oxidized with tetrapropylammonium perrhuthenate in dichloromethane, giving the corresponding aldehyde (rac)-(XVI).
| 【1】 Sawada, D.; et al.; Enantioselective total synthesis of epothilones A and B using multifunctional asymmetric catalysis. J Am Chem Soc 2000, 122, 43, 10521. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 12641 | Neopentyl glycol; 2,2-Dimethyl-1,3-propanediol | 126-30-7 | C5H12O2 | 详情 | 详情 |
| (II) | 44529 | 3-(benzyloxy)-2,2-dimethyl-1-propanol | C12H18O2 | 详情 | 详情 | |
| (III) | 44504 | 3-(benzyloxy)-2,2-dimethylpropanal | C12H16O2 | 详情 | 详情 | |
| (IV) | 33891 | Methyl ethyl ketone; 2-Butanone | 78-93-3 | C4H8O | 详情 | 详情 |
| (V) | 44505 | (E)-7-(benzyloxy)-6,6-dimethyl-4-hepten-3-one | C16H22O2 | 详情 | 详情 | |
| (VI) | 44506 | 1-[3-[2-(benzyloxy)-1,1-dimethylethyl]-2-oxiranyl]-1-propanone | C16H22O3 | 详情 | 详情 | |
| (VII) | 44507 | 1-[3-[2-(benzyloxy)-1,1-dimethylethyl]-2-oxiranyl]-1-propanone O-methyloxime | C17H25NO3 | 详情 | 详情 | |
| (VIII) | 44508 | (4R,5R)-7-(benzyloxy)-5-hydroxy-4,6,6-trimethyl-3-heptanone O-methyloxime | C18H29NO3 | 详情 | 详情 | |
| (IX) | 44509 | (4S,5R)-7-(benzyloxy)-5-hydroxy-4,6,6-trimethyl-3-heptanone | C17H26O3 | 详情 | 详情 | |
| (X) | 11463 | 3-Bromo-1-propene; 3-Bromopropene；allyl bromide | 106-95-6 | C3H5Br | 详情 | 详情 |
| (XI) | 44510 | (4S,6S,7R)-9-(benzyloxy)-7-hydroxy-4,6,8,8-tetramethyl-1-nonen-5-one | C20H30O3 | 详情 | 详情 | |
| (XII) | 44511 | (3R,4R,5S,6S)-1-(benzyloxy)-2,2,4,6-tetramethyl-8-nonene-3,5-diol | C20H32O3 | 详情 | 详情 | |
| (XIII) | 17354 | isopropenyl methyl ether; 2-methoxy-1-propene | 116-11-0 | C4H8O | 详情 | 详情 |
| (XIV) | 44512 | benzyl 2-methyl-2-[(4R,5S,6S)-2,2,5-trimethyl-6-[(1S)-1-methyl-3-butenyl]-1,3-dioxan-4-yl]propyl ether; (4R,5S,6S)-4-[2-(benzyloxy)-1,1-dimethylethyl]-2,2,5-trimethyl-6-[(1S)-1-methyl-3-butenyl]-1,3-dioxane | C23H36O3 | 详情 | 详情 | |
| (XV) | 44513 | 2-methyl-2-[(4R,5S,6S)-2,2,5-trimethyl-6-[(1S)-1-methyl-3-butenyl]-1,3-dioxan-4-yl]-1-propanol | C16H30O3 | 详情 | 详情 | |
| (XVI) | 44514 | 2-methyl-2-[(4R,5S,6S)-2,2,5-trimethyl-6-[(1S)-1-methyl-3-butenyl]-1,3-dioxan-4-yl]propanal | C16H28O3 | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号：(IV)Synthesis of undecenoic ester intermediate (XXI): The reaction of 2,2-dimethylpropane-1,3-diol (I) with benzaldehyde, Ts-OH and DIBAL gives the monobenzyl ether (II), which is oxidized with SO3/pyridine in dichloromethane, yielding the propionaldehyde (III). The condensation of (III) with butanone (IV) by means of LDA and TFAA affords the heptenone (V), which is epoxidated with H2O2 and NaOH in aq. methanol to provide the racemic epoxide (rac)-(VI). The reaction of ketone (VI) with O-methylhydroxylamine and NaOAc in methanol gives the corresponding oxime (rac)-(VII), which is treated with CuCN and Me-Li in ethyl ether to yield the beta-hydroxy oxime (rac)-(VIII). The treatment of (VIII) with H2 and RaNi in acetone/THF affords the corresponding beta-hydroxy ketone (rac)-(IX), which is allylated with allyl bromide (X) and LHMDS in the presence of 1,3-dimethylperhydropyrimidin-2-one to give the beta-hydroxynonen-5-one (rac)-(XI). The reduction of (XI) with Me4NBH(OAc)3 and HOAc in acetonitrile yields the diol (rac)-(XII), which is protected with 2-methoxypropene (XIII) and Ts-OH, affording the 1,3-dioxane (rac)-(XIV). The reaction of (XIV) with Li in liquid ammonia, tert-butanol and THF provides the debenzylated primary alcohol (rac)-(XV), which is oxidized with tetrapropylammonium perrhuthenate in dichloromethane, giving the corresponding aldehyde (rac)-(XVI).
| 【1】 Sawada, D.; et al.; Enantioselective total synthesis of epothilones A and B using multifunctional asymmetric catalysis. J Am Chem Soc 2000, 122, 43, 10521. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 12641 | Neopentyl glycol; 2,2-Dimethyl-1,3-propanediol | 126-30-7 | C5H12O2 | 详情 | 详情 |
| (II) | 44529 | 3-(benzyloxy)-2,2-dimethyl-1-propanol | C12H18O2 | 详情 | 详情 | |
| (III) | 44504 | 3-(benzyloxy)-2,2-dimethylpropanal | C12H16O2 | 详情 | 详情 | |
| (IV) | 33891 | Methyl ethyl ketone; 2-Butanone | 78-93-3 | C4H8O | 详情 | 详情 |
| (V) | 44505 | (E)-7-(benzyloxy)-6,6-dimethyl-4-hepten-3-one | C16H22O2 | 详情 | 详情 | |
| (VI) | 44506 | 1-[3-[2-(benzyloxy)-1,1-dimethylethyl]-2-oxiranyl]-1-propanone | C16H22O3 | 详情 | 详情 | |
| (VII) | 44507 | 1-[3-[2-(benzyloxy)-1,1-dimethylethyl]-2-oxiranyl]-1-propanone O-methyloxime | C17H25NO3 | 详情 | 详情 | |
| (VIII) | 44508 | (4R,5R)-7-(benzyloxy)-5-hydroxy-4,6,6-trimethyl-3-heptanone O-methyloxime | C18H29NO3 | 详情 | 详情 | |
| (IX) | 44509 | (4S,5R)-7-(benzyloxy)-5-hydroxy-4,6,6-trimethyl-3-heptanone | C17H26O3 | 详情 | 详情 | |
| (X) | 11463 | 3-Bromo-1-propene; 3-Bromopropene；allyl bromide | 106-95-6 | C3H5Br | 详情 | 详情 |
| (XI) | 44510 | (4S,6S,7R)-9-(benzyloxy)-7-hydroxy-4,6,8,8-tetramethyl-1-nonen-5-one | C20H30O3 | 详情 | 详情 | |
| (XII) | 44511 | (3R,4R,5S,6S)-1-(benzyloxy)-2,2,4,6-tetramethyl-8-nonene-3,5-diol | C20H32O3 | 详情 | 详情 | |
| (XIII) | 17354 | isopropenyl methyl ether; 2-methoxy-1-propene | 116-11-0 | C4H8O | 详情 | 详情 |
| (XIV) | 44512 | benzyl 2-methyl-2-[(4R,5S,6S)-2,2,5-trimethyl-6-[(1S)-1-methyl-3-butenyl]-1,3-dioxan-4-yl]propyl ether; (4R,5S,6S)-4-[2-(benzyloxy)-1,1-dimethylethyl]-2,2,5-trimethyl-6-[(1S)-1-methyl-3-butenyl]-1,3-dioxane | C23H36O3 | 详情 | 详情 | |
| (XV) | 44513 | 2-methyl-2-[(4R,5S,6S)-2,2,5-trimethyl-6-[(1S)-1-methyl-3-butenyl]-1,3-dioxan-4-yl]-1-propanol | C16H30O3 | 详情 | 详情 | |
| (XVI) | 44514 | 2-methyl-2-[(4R,5S,6S)-2,2,5-trimethyl-6-[(1S)-1-methyl-3-butenyl]-1,3-dioxan-4-yl]propanal | C16H28O3 | 详情 | 详情 |
合成路线6
该中间体在本合成路线中的序号：(XI)Claisen condensation between diethyl oxalate (X) and 2-butanone (XI) leads to the diketo ester (XII), which is subsequently cyclized with hydrazine hydrate to furnish the pyrazolecarboxylate (XIII). After alkaline hydrolysis of ester (XIII), the resultant pyrazolecarboxylic acid (XIV) is nitrated by fuming HNO3 in hot H2SO4 to provide (XV). Chlorination of acid (XV) with SOCl2, followed by treatment with ammonia in THF yields the pyrazolecarboxamide (XVI). The alkylation of pyrazole (XVI) with iodomethane and Cs2CO3 leads to a mixture of N-methylated regioisomers (XVII) and (XVIII), which are separated by crystallization, followed by column chromatography. The desired isomer (XVII) is further reduced by catalytic hydrogenation to the aminopyrazole (XIX)
| 【1】 Street, S.D.A.; Wood, A.; Bunnage, M.E.; Mathias, J.P. (Pfizer Inc.; Pfizer Ltd.); Pyrazolopyrimidinone cGMP PDE5 inhibitors for the treatment of sexual dysfunction. WO 9954333 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (X) | 17571 | Diethyl oxalate; Ethyl 2-ethoxy-2-oxoacetate | 95-92-1 | C6H10O4 | 详情 | 详情 |
| (XI) | 33891 | Methyl ethyl ketone; 2-Butanone | 78-93-3 | C4H8O | 详情 | 详情 |
| (XII) | 62099 | ethyl 2,4-dioxohexanoate | C8H12O4 | 详情 | 详情 | |
| (XIII) | 62100 | ethyl 3-ethyl-1H-pyrazole-5-carboxylate | C8H12N2O2 | 详情 | 详情 | |
| (XIV) | 62101 | 3-ethyl-1H-pyrazole-5-carboxylic acid | C6H8N2O2 | 详情 | 详情 | |
| (XV) | 62102 | 3-ethyl-4-nitro-1H-pyrazole-5-carboxylic acid | C6H7N3O4 | 详情 | 详情 | |
| (XVI) | 62103 | 3-ethyl-4-nitro-1H-pyrazole-5-carboxamide | C6H8N4O3 | 详情 | 详情 | |
| (XVII) | 62105 | 5-ethyl-1-methyl-4-nitro-1H-pyrazole-3-carboxamide | C7H10N4O3 | 详情 | 详情 | |
| (XVIII) | 62104 | 3-ethyl-1-methyl-4-nitro-1H-pyrazole-5-carboxamide | C7H10N4O3 | 详情 | 详情 | |
| (XIX) | 62106 | 4-amino-5-ethyl-1-methyl-1H-pyrazole-3-carboxamide | C7H12N4O | 详情 | 详情 |