【结 构 式】 |
【分子编号】34024 【品名】2-[4-(2-thienylcarbonyl)phenyl]propanenitrile 【CA登记号】 |
【 分 子 式 】C14H11NOS 【 分 子 量 】241.31348 【元素组成】C 69.68% H 4.59% N 5.8% O 6.63% S 13.29% |
合成路线1
该中间体在本合成路线中的序号:(VIII)The reaction of 1-(4-bromophenyl)ethanol (IV) with 3,4-dihydro-2H-pyran (C) by means of HCl yields 2-[1-(4-bromophenyl)ethoxy]tetrahydro-2H-pyran (V); this product by condensation with 2-thiophenecarbonitrile (D) through its Grignard complex in THF gives [4-(1-hydroxyethyl)phenyl](2-thienyl)ketone (VI), which without purification is treated with SOCl2 in benzene to give [4-(1-chloroethyl)phenyl](2-thienyl)ketone (VII); then the halogen is substituted by CN with NaCN in DMSO to afford alpha-methyl-4-(2-thienylcarbonyl)benzeneacetonitrile (VIII), which, without purification, is hydrolyzed with H2SO4 and acetic acid.
【1】 Van Daele, P.G.H.; et al.; Synthesis of alpha-methyl-4-(2-thienylcarbonyl)benzene acetic acid, suprofen and derivatives. Arzneim-Forsch Drug Res 1975, 25, 10, 1495-1501. |
【2】 Castaner, J.; Chatterjee, S.S.; Suprofen. Drugs Fut 1976, 1, 3, 148. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(D) | 34025 | Thiophene-2-carbonitrile; 2-thiophenecarbonitrile | 1003-31-2 | C5H3NS | 详情 | 详情 |
(IV) | 34019 | diethyl 2-methyl-2-[4-(2-thienylcarbonyl)phenyl]malonate | C19H20O5S | 详情 | 详情 | |
(V) | 34021 | 1-(4-bromophenyl)ethyl tetrahydro-2H-pyran-2-yl ether; 2-[1-(4-bromophenyl)ethoxy]tetrahydro-2H-pyran | C13H17BrO2 | 详情 | 详情 | |
(VI) | 34022 | [4-(1-hydroxyethyl)phenyl](2-thienyl)methanone | C13H12O2S | 详情 | 详情 | |
(VII) | 34023 | [4-(1-chloroethyl)phenyl](2-thienyl)methanone | C13H11ClOS | 详情 | 详情 | |
(VIII) | 34024 | 2-[4-(2-thienylcarbonyl)phenyl]propanenitrile | C14H11NOS | 详情 | 详情 | |
(C) | 13684 | 3,4-Dihydro-2H-pyran;2,3-Dihydro-4H-pyran; 5,6-Dihydro-4H-pyran;Dihydropyran | 110-87-2 | C5H8O | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(VIII)The condensation of thiophene (E) and 4-ethylbenzoyl chloride (IX) by means of SnCl4 in CH2Cl2 gives (4-ethylphenyl)(2-thienyl)ketone (X), which is brominated with N-bromosuccidine and benzoyl peroxide in CCl4 to [4-(1-bromoethyl)phenyl](2-thienyl)ketone (XI); then this product is treated with NaCN in DMSO to obtain the acetonitrile (VIII), which, without purification, is hydrolyzed with H2SO4 and acetic acid.
【1】 Van Daele, P.G.H.; et al.; Synthesis of alpha-methyl-4-(2-thienylcarbonyl)benzene acetic acid, suprofen and derivatives. Arzneim-Forsch Drug Res 1975, 25, 10, 1495-1501. |
【2】 Castaner, J.; Chatterjee, S.S.; Suprofen. Drugs Fut 1976, 1, 3, 148. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(E) | 13297 | Thiophene | 110-02-1 | C4H4S | 详情 | 详情 |
(VIII) | 34024 | 2-[4-(2-thienylcarbonyl)phenyl]propanenitrile | C14H11NOS | 详情 | 详情 | |
(IX) | 34026 | 4-ethylbenzoyl chloride | 16331-45-6 | C9H9ClO | 详情 | 详情 |
(X) | 34027 | (4-ethylphenyl)(2-thienyl)methanone | C13H12OS | 详情 | 详情 | |
(XI) | 34028 | [4-(1-bromoethyl)phenyl](2-thienyl)methanone | C13H11BrOS | 详情 | 详情 |