【结 构 式】 |
【分子编号】22631 【品名】3-bromopropyl 3-oxobutanoate 【CA登记号】 |
【 分 子 式 】C7H11BrO3 【 分 子 量 】223.06654 【元素组成】C 37.69% H 4.97% Br 35.82% O 21.52% |
合成路线1
该中间体在本合成路线中的序号:(VI)By cyclization of 3-nitrobenzaldehyde (I) with 3-nitratopropyl-3-aminocrotonate (II) and 2-nitratopropyl acetoacetate (III) in refluxing benzene. The starting products (II) and (III) are obtained as follows: The reaction of diketene (IV) with 3-bromopropanol (V) by means of sodium acetate at 50 C gives 3-bromopropyl acetoacetate (VI), which by reaction with AgNO3 in refluxing acetonitrile is converted to 3-nitratopropyl acetoacetate (VII). Finally, this compound is treated with NH3 in THF to afford the aminocrotonic ester (II). The reaction of diketene (IV) with 2-chloropropanol (VIII) as before gives 2-chloropropyl acetoacetate (IX), which is treated with AgNO3 as before to yield acetoacetate (III).
【1】 Hatayama, K.; Sawada, J.; Nakazato, A.; Ogawa, T.; Ito, S. (Taisho Pharmaceutical Co., Ltd.); 1,4-Dihydropyridine derivs.. EP 0092936; US 4472411 . |
【2】 Prous, J.; Castaner, J.; CD-349. Drugs Fut 1988, 13, 7, 610. |
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) | 12646 | 3-Nitrobenzaldehyde | 99-61-6 | C7H5NO3 | 详情 | 详情 |
(II) | 13999 | 3-(nitrooxy)propyl (E)-3-amino-2-butenoate | C7H12N2O5 | 详情 | 详情 | |
(III) | 22628 | 2-(nitrooxy)propyl 3-oxobutanoate | C7H11NO6 | 详情 | 详情 | |
(IV) | 21896 | 4-methyl-2H-oxet-2-one | C4H4O2 | 详情 | 详情 | |
(V) | 12573 | 3-Bromo-1-propanol; 3-Bromopropanol | 627-18-9 | C3H7BrO | 详情 | 详情 |
(VI) | 22631 | 3-bromopropyl 3-oxobutanoate | C7H11BrO3 | 详情 | 详情 | |
(VII) | 22632 | 3-(nitrooxy)propyl 3-oxobutanoate | C7H11NO6 | 详情 | 详情 | |
(VIII) | 22633 | 2-chloro-1-propanol | 78-89-7 | C3H7ClO | 详情 | 详情 |
(IX) | 22634 | 2-chloropropyl 3-oxobutanoate | C7H11ClO3 | 详情 | 详情 |