【结 构 式】 ![]() |
【分子编号】59599 【品名】3-methoxy-4-(2-oxiranylmethoxy)benzaldehyde 【CA登记号】 |
【 分 子 式 】C11H12O4 【 分 子 量 】208.21388 【元素组成】C 63.45% H 5.81% O 30.74% |
合成路线1
该中间体在本合成路线中的序号:(III)The condensation of vanillin (I) with epichlorohydrin (II) in ethanolic NaOH produced the glycidyl ether (III). Epoxide ring opening in (III) by means of tert-butylamine (IV) in EtOH furnished amino alcohol (V). The title dihydropyridine derivative was then obtained by reaction between aldehyde (V), methyl acetoacetate (VI), ammonia under Hantzsch condensation conditions, and was isolated after conversion to the hydrochloride salt.
【1】 Liang, J.-C.; Chen, I.-J.; Tsai, C.-H.; Liou, S.-F.; Wang, C.-S.; Yeh, J.-L.; The new generation dihydropyridine type calcium blockers, bearing 4-phenyl oxypropanolamine, display alpha-/beta-adrenoceptor antagonist and long-acting antihypertensive activities. Bioorg Med Chem 2002, 10, 3, 719. |
【2】 Donovan, S. (Allergan, Inc.); Method for treating a neoplasm. WO 0209743 . |
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) | 22701 | 4-hydroxy-3-methoxybenzaldehyde | 121-33-5 | C8H8O3 | 详情 | 详情 |
(II) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
(III) | 59599 | 3-methoxy-4-(2-oxiranylmethoxy)benzaldehyde | C11H12O4 | 详情 | 详情 | |
(IV) | 17895 | 2-Amino-2-methylpropane; tert-butylamine; 2-methyl-2-propanamine | 75-64-9 | C4H11N | 详情 | 详情 |
(V) | 59600 | 4-[3-(tert-butylamino)-2-hydroxypropoxy]-3-methoxybenzaldehyde | C15H23NO4 | 详情 | 详情 | |
(VI) | 11791 | methyl 3-oxobutanoate; Methyl acetoacetate | 105-45-3 | C5H8O3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(IX)The condensation of vanillin (VII) with epichlorohydrin (VIII) in ethanolic NaOH produced the glycidyl ether (IX). Epoxide ring opening in (IX) by means of amine (VI) in EtOH furnished amino alcohol (X). The title dihydropyridine derivative was then obtained by reaction between aldehyde (X), methyl acetoacetate (XI), and ammonia under Hantzsch condensation conditions.
【1】 Liang, J.-C.; Chen, I.-J.; Tsai, C.-H.; Liou, S.-F.; Wang, C.-S.; Yeh, J.-L.; The new generation dihydropyridine type calcium blockers, bearing 4-phenyl oxypropanolamine, display alpha-/beta-adrenoceptor antagonist and long-acting antihypertensive activities. Bioorg Med Chem 2002, 10, 3, 719. |
【2】 Lin, T.-H.; Chen, I.-J.; Guaiacoxypropanolamines with alpha/beta-adrenergic blocking activity. EP 1108710; WO 0005209 . |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(VI) | 31105 | 2-(2-methoxyphenoxy)ethylamine; 2-(2-methoxyphenoxy)-1-ethanamine | 1836-62-0 | C9H13NO2 | 详情 | 详情 |
(VII) | 22701 | 4-hydroxy-3-methoxybenzaldehyde | 121-33-5 | C8H8O3 | 详情 | 详情 |
(VIII) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
(IX) | 59599 | 3-methoxy-4-(2-oxiranylmethoxy)benzaldehyde | C11H12O4 | 详情 | 详情 | |
(X) | 59618 | 4-(2-hydroxy-3-{[2-(2-methoxyphenoxy)ethyl]amino}propoxy)-3-methoxybenzaldehyde | C20H25NO6 | 详情 | 详情 | |
(XI) | 11791 | methyl 3-oxobutanoate; Methyl acetoacetate | 105-45-3 | C5H8O3 | 详情 | 详情 |