【结 构 式】 |
【分子编号】51791 【品名】methyl (Z)-3-hydroxy-4-phenyl-2-butenoate 【CA登记号】 |
【 分 子 式 】C11H12O3 【 分 子 量 】192.21448 【元素组成】C 68.74% H 6.29% O 24.97% |
合成路线1
该中间体在本合成路线中的序号:(I)When 4-phenyl-3-oxobutanoic acid methyl ester (I) were reacted with thiourea (II), in the presence of sodium methoxide, condensation occurred with formation of 3,4-dihydro-6-benzyl-4-oxo-2-thioxopyrimidine (III). Reaction of compound (III) with cyclopentyl chloride (IV) in alkaline medium afforded the required 2-(cyclopentylthio)-6-benzyl-3,4-dihydro-4-oxopyrimidine.
【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159. |
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) | 51791 | methyl (Z)-3-hydroxy-4-phenyl-2-butenoate | C11H12O3 | 详情 | 详情 | |
(II) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
(III) | 51793 | 6-benzyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone | C11H10N2OS | 详情 | 详情 | |
(IV) | 51794 | 1-Chlorocyclopentane; Chlorocyclopentane; cyclopentyl chloride | 930-28-9 | C5H9Cl | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(I)Condensation of 4-phenyl-3-oxobutanoic acid methyl ester (I) with O-methyl isourea (II) led to the formation of 6-benzyl-3,4-dihydro-2-methoxy-4-oxopyrimidine (III). Subsequent displacement of the methoxy group linked at C-2 of the pyrimidine ring by treatment with isobutoxy sodium salt (IV) furnished 2-isobutoxy-6-benzyl-3,4-dihydro-4-oxopyrimidine
【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159. |
合成路线3
该中间体在本合成路线中的序号:(I)Condensation of 4-phenyl-3-oxobutanoic acid methyl ester (I) with O-methyl isourea (II) led to the formation of 6-benzyl-3,4-dihydro-2-methoxy-4-oxopyrimidine (III). Subsequent displacement of the methoxy group linked at C-2 of the pyrimidine ring by treatment with cyclohexoxy sodium salt (IV) furnished 2-cyclohexoxy-6-benzyl-3,4-dihydro-4-oxopyrimidine.
【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159. |
合成路线4
该中间体在本合成路线中的序号:(I)When 4-phenyl-3-oxobutanoic acid methyl ester (I) were reacted with thiourea (II), in the presence of sodium methoxide, condensation occurred with formation of 3,4-dihydro-6-benzyl-4-oxo-2-thioxopyrimidine (III). Reaction of the compound (III) with methyl chloride (IV) in alkaline medium afforded the required 2-(methylthio)-6-benzyl-3,4-dihydro-4-oxopyrimidine
【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159. |
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) | 51791 | methyl (Z)-3-hydroxy-4-phenyl-2-butenoate | C11H12O3 | 详情 | 详情 | |
(II) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
(III) | 51793 | 6-benzyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone | C11H10N2OS | 详情 | 详情 | |
(IV) | 51798 | methyl chloride; Monochloromethane; Artic; Chloromethane | 74-87-3 | CH3Cl | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号:(I)When 4-phenyl-3-oxobutanoic acid methyl ester (I) were reacted with thiourea (II), in the presence of sodium methoxide, condensation occurred with formation of 3,4-dihydro-6-benzyl-4-oxo-2-thioxopyrimidine (III). Reaction of the compound (III) with isopropyl chloride (IV) in alkaline medium afforded the required 2-(isopropylthio)-6-benzyl-3,4-dihydro-4-oxopyrimidine
【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159. |
合成路线6
该中间体在本合成路线中的序号:(I)When 4-phenyl-3-oxobutanoic acid methyl ester (I) were reacted with thiourea (II), in the presence of sodium methoxide, condensation occurred with formation of 3,4-dihydro-6-benzyl-4-oxo-2-thioxopyrimidine (III). Reaction of the compound (III) with isobutyl chloride (IV) in alkaline medium afforded the required 2-(isobutylthio)-6-benzyl-3,4-dihydro-4-oxopyrimidine
【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159. |
合成路线7
该中间体在本合成路线中的序号:(I)When 4-phenyl-3-oxobutanoic acid methyl ester (I) were reacted with thiourea (II), in the presence of sodium methoxide, condensation occurred with formation of 3,4-dihydro-6-benzyl-4-oxo-2-thioxopyrimidine (III). Reaction of the compound (III) with cyclohexyl chloride (IV) in alkaline medium afforded the required 2-(cyclohexylthio)-6-benzyl-3,4-dihydro-4-oxopyrimidine
【1】 Artico, M.; Selected non-nucleoside reverse transcriptase inhibitors (NNRTIs): the DABOs family. Drugs Fut 2002, 27, 2, 159. |
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) | 51791 | methyl (Z)-3-hydroxy-4-phenyl-2-butenoate | C11H12O3 | 详情 | 详情 | |
(II) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
(III) | 51793 | 6-benzyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone | C11H10N2OS | 详情 | 详情 | |
(IV) | 51795 | chlorocyclohexane; Hexahydrochlorobenzene; Cyclohexyl chloride | 542-18-7 | C6H11Cl | 详情 | 详情 |