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【结 构 式】 
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【分子编号】16637 【品名】1-[2-hydroxy-4-[(3-methyl-2-butenyl)oxy]phenyl]-1-ethanone 【CA登记号】 |
【 分 子 式 】C13H16O3 【 分 子 量 】220.26824 【元素组成】C 70.89% H 7.32% O 21.79% |
合成路线1
该中间体在本合成路线中的序号：(I)The reaction of 2-hydroxy-4-(3-methyl-2-butenyloxy)acetophenone (I) with ethyl bromoacetate (II) by means of KOH in acetone gives 2-ethoxycarbonylmethoxy-4-(3-methyl-2-butenyloxy)acetophenone (III), which is then condensed with 4-(3-methyl-2-butenyloxy)benzaldehyde (IV) by means of KOH in ethanol.
| 【1】 Grau, M.; Castaner, J.; Blancafort, P.; Serradell, M.N.; SU-88. Drugs Fut 1983, 8, 6, 513. |
| 【2】 Kyogoku, K.; Hatayama, K.; Yokomori, S.; Sawada, J.; Tanaka, I. (Taisho Pharmaceutical Co., Ltd.); 2-(Carboxymethoxy)chalcones. DE 2705603; ES 455620; FR 2340924; GB 1523241; JP 52097950; US 4085135 . |
| 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) | 16637 | 1-[2-hydroxy-4-[(3-methyl-2-butenyl)oxy]phenyl]-1-ethanone | C13H16O3 | 详情 | 详情 | |
| (II) | 16640 | Ethyl 2-bromoacetate; Ethyl bromoacetate | 105-36-2 | C4H7BrO2 | 详情 | 详情 |
| (III) | 36017 | ethyl 2-[2-acetyl-5-[(3-methyl-2-butenyl)oxy]phenoxy]acetate | C17H22O5 | 详情 | 详情 | |
| (IV) | 19019 | 4-[(3-methyl-2-butenyl)oxy]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：(I)The synthesis of free compound is performed as follows: The condensation of 2-hydroxy-4-(3-methyl-2-butenyloxy)acetophenone (I) with 4-tert-butylbenzaldehyde (II) by means of KOH in hot ethanol gives 3-(4-tert-butylphenyl)-1-[4-hydroxy-4-(3-methyl-2-butenyloxy)phenyl]-2(E)-propen-1-one (III), which is condensed with ethyl bromoacetate (IV) by means of KOH in acetone to afford (E)-2-[2-(4-tert-butylcinnamoyl)-4-(3-methyl-2-butenyloxy)phenoxy] acetic acid ethyl ester (V). Finally, this compound is hydrolyzed with KOH in hot ethanol-water.
| 【1】 Yokomori, S.; Saijo, K.; Matsunaga, T.; Nakashima, Y.; Hatayama, K. (Taisho Pharmaceutical Co., Ltd.); Chalcone derivs. EP 0412803; JP 1991163042 . |
| 【2】 Yokomori, S.; Saijo, K.; Hatayama, M. (Taisho Pharmaceutical Co., Ltd.); Antiulcerative agents. JP 1993058885 . |
| 【3】 Rabasseda, X.; Castañer, J.; Mealy, N.; SU-840. Drugs Fut 1994, 19, 10, 923. |
| 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) | 16637 | 1-[2-hydroxy-4-[(3-methyl-2-butenyl)oxy]phenyl]-1-ethanone | C13H16O3 | 详情 | 详情 | |
| (II) | 16638 | 4-(tert-butyl)benzaldehyde; 4-tert-Butyl-benzaldehyde | 939-97-9 | C11H14O | 详情 | 详情 |
| (III) | 16639 | (E)-3-[4-(tert-butyl)phenyl]-1-[2-hydroxy-4-[(3-methyl-2-butenyl)oxy]phenyl]-2-propen-1-one | C24H28O3 | 详情 | 详情 | |
| (IV) | 16640 | Ethyl 2-bromoacetate; Ethyl bromoacetate | 105-36-2 | C4H7BrO2 | 详情 | 详情 |
| (V) | 16641 | ethyl 2-[2-[(E)-3-[4-(tert-butyl)phenyl]-2-propenoyl]-5-[(3-methyl-2-butenyl)oxy]phenoxy]acetate | C28H34O5 | 详情 | 详情 |