• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】46519

【品名】4-[(E)-3-ethoxy-1-propenyl]benzaldehyde

【CA登记号】

【 分 子 式 】C12H14O2

【 分 子 量 】190.24196

【元素组成】C 75.76% H 7.42% O 16.82%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(VII)

Palladium-catalyzed coupling of 4-bromobenzaldehyde (I) with methyl acrylate (II) furnished methyl 4-formylcinnamate (III). After aldehyde protection as the ethylene acetal (IV), ester group reduction using DIBAL in cold CH2Cl2 gave rise to the cinnamyl alcohol (V). O-Alkylation of (V) with ethyl iodide in the presence of NaH produced the corresponding ethyl ether (VI). The acetal protecting group of (VI) was then hydrolyzed with HCl to yield aldehyde (VII).

2 Zhang, C.; Mjalli, A.M.M. (Ontogen Corp.); Imidazole derivs. as MDR modulators. EP 0999835; US 5840721; WO 9902155 .
1 Dixon, R.; Zhang, C.; Sarshar, S.; Mjalli, A.M.M.; Rodarte, J.C.; Moran, E.J.; Benbatoul, K.D.; Krane, S.; 2,4,5-Trisubstituted imidazoles: Novel nontoxic modulators of P-glycoprotein mediated multidrug resistance. Part 2. Bioorg Med Chem Lett 2000, 10, 23, 2603.
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) 22231 4-Bromobenzaldehyde 1122-91-4 C7H5BrO 详情 详情
(II) 14156 methyl acrylate 96-33-3 C4H6O2 详情 详情
(III) 46515 methyl (E)-3-(4-formylphenyl)-2-propenoate 7560-50-1 C11H10O3 详情 详情
(IV) 46516 methyl (E)-3-[4-(1,3-dioxolan-2-yl)phenyl]-2-propenoate C13H14O4 详情 详情
(V) 46517 (E)-3-[4-(1,3-dioxolan-2-yl)phenyl]-2-propen-1-ol C12H14O3 详情 详情
(VI) 46518 (E)-3-[4-(1,3-dioxolan-2-yl)phenyl]-2-propenyl ethyl ether; 2-[4-[(E)-3-ethoxy-1-propenyl]phenyl]-1,3-dioxolane C14H18O3 详情 详情
(VII) 46519 4-[(E)-3-ethoxy-1-propenyl]benzaldehyde C12H14O2 详情 详情

合成路线2

该中间体在本合成路线中的序号:(VII)

Treatment of 4,4'-difluorobenzyl (VIII) with isopropylamine and K2CO3 in hot DMSO produced 4,4'-bis(isopropylamino)benzyl (IX). This was then condensed with the intermediate aldehyde (VII) in the presence of ammonium acetate in HOAc to produce the target triaryl imidazole.

2 Zhang, C.; Mjalli, A.M.M. (Ontogen Corp.); Imidazole derivs. as MDR modulators. EP 0999835; US 5840721; WO 9902155 .
1 Dixon, R.; Zhang, C.; Sarshar, S.; Mjalli, A.M.M.; Rodarte, J.C.; Moran, E.J.; Benbatoul, K.D.; Krane, S.; 2,4,5-Trisubstituted imidazoles: Novel nontoxic modulators of P-glycoprotein mediated multidrug resistance. Part 2. Bioorg Med Chem Lett 2000, 10, 23, 2603.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 46519 4-[(E)-3-ethoxy-1-propenyl]benzaldehyde C12H14O2 详情 详情
(VIII) 46520 1,2-bis(4-fluorophenyl)-1,2-ethanedione C14H8F2O2 详情 详情
(IX) 46521 1,2-bis[4-(isopropylamino)phenyl]-1,2-ethanedione C20H24N2O2 详情 详情
Extended Information