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【结 构 式】 
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【分子编号】16899 【品名】2-(Acetoxy)benzoic acid; Aspirin; Acetylsalicylic acid 【CA登记号】50-78-2 |
【 分 子 式 】C9H8O4 【 分 子 量 】180.16012 【元素组成】C 60% H 4.48% O 35.52% |
合成路线1
该中间体在本合成路线中的序号：(III)2) By condensation of an organic salt of 2-acetyloxybenzoic acid (III) with 3-bromophthalide.
| 【1】 Los, M.A. (Laboratorios Bagó); Methods of treating mammals suffering from inflammation and pain. BE 0858864; JP 8162049; US 4256760 . |
| 【2】 Castaner, J.; Prous, J.; Talosalate. Drugs Fut 1986, 11, 5, 394. |
合成路线2
该中间体在本合成路线中的序号：(I)Acetylsalicylic acid (I) was converted to acid chloride (II) by refluxing in a SOCl2 solution. Condensation of acid chloride (II) with guaiacol (III) either in the absence or in the presence of tertiary amines gave rise to the target orthoester derivative. Alternatively, the title compound has been prepared by treatment of acetylsalicylic acid (I) with several acid anhydrides, followed by guaiacol (III).
| 【1】 Hundewadt, M.; Senning, A.; Aspirin prodrugs: 2-Methyl-2-aryloxy-4H-1,3-benzodioxin-4-ones acting as true aspirin prodrugs. Acta Chem Scand 1990, 44, 7, 746. |
| 【2】 Quadro, G. (Dr. Lo. Zambeletti SpA); 2,4-Dioxacyclohexanone deriv.. BE 0890731; US 4358444 . |
| 【3】 Beck, C.; Preparation of 3-methyl-3-(O-methoxyphenoxy)benzo-2,4-dioxacycloheanone. GB 2101127 . |
合成路线3
该中间体在本合成路线中的序号：(I)Acetylsalicylic (I) acid was refluxed in SOCl2 to give acetylsalicylyl chloride (II), which is condensed with maltol (III) by means of triethylamine in chloroform to afford aspalatone.
| 【1】 Underwood, M.J.; More, R.S.; The aspirin papers. Brit Med J 1994, 308, 71-2. |
| 【2】 Han, B.H.; Suh, D.-Y.; Yang, H.O.; Park, Y.-H.; Kang, Y.H.; Kim, Y.C.; Synthesis and antiplatelet effects of the new antithrombotic agent aspalatone with low ulcerogenicity. Arzneim-Forsch Drug Res 1994, 44, 10, 1122-6. |
| 【3】 Han, B.H.; Aspalatone. Drugs Fut 1995, 20, 11, 1109. |
| 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) | 16899 | 2-(Acetoxy)benzoic acid; Aspirin; Acetylsalicylic acid | 50-78-2 | C9H8O4 | 详情 | 详情 |
| (II) | 16900 | 2-(chlorocarbonyl)phenyl acetate; Acetylsalicyloyl chloride | 5538-51-2 | C9H7ClO3 | 详情 | 详情 |
| (III) | 13671 | Hydroxymethylpyrone; 3-Hydroxy-2-methyl-4H-pyran-4-one；Maltol;3-Hydroxy-2-methyl-4-pyrone | 118-71-8 | C6H6O3 | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(I)Reaction of acetylsalicylic acid (I) with 4-bromomethyl-3-carbamoylfuroxan (II) provides the furoxanylmethyl ester (III). Subsequent trifluoroacetic anhydride-promoted dehydration of amide (III) yields the corresponding cyano derivative.
| 【1】 Cena, C.; Lolli, M.L.; Lazzarato, L.; Guaita, E.; Morini, G.; Coruzzi, G.; McElroy, S.P.; Megson, I.L.; Fruttero, R.; Gasco, A.; Antiinflammatory, gastrosparing, and antiplatelet properties of new NO-donor esters of aspirin. J Med Chem 2003, 46, 5, 747. |
| 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) | 16899 | 2-(Acetoxy)benzoic acid; Aspirin; Acetylsalicylic acid | 50-78-2 | C9H8O4 | 详情 | 详情 |
| (II) | 64270 | 3-(aminocarbonyl)-4-(bromomethyl)-1,2,5-oxadiazol-2-ium-2-olate | C4H4BrN3O3 | 详情 | 详情 | |
| (III) | 64271 | 4-({[2-(acetyloxy)benzoyl]oxy}methyl)-3-(aminocarbonyl)-1,2,5-oxadiazol-2-ium-2-olate | C13H11N3O7 | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号：(II)
| 【1】 Rossignol JF. 2006. Alkylbenzamides. US20060194853 |
| 【2】 Rossignol JF, Cavier R 1976. New derivatives of 2-benzamido-5-nitro thiazoles. US 3950351 |
| 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) | 15240 | 2-Hydroxybenzoic acid; Salicylic acid | 69-72-7 | C7H6O3 | 详情 | 详情 |
| (II) | 16899 | 2-(Acetoxy)benzoic acid; Aspirin; Acetylsalicylic acid | 50-78-2 | C9H8O4 | 详情 | 详情 |
| (III) | 16900 | 2-(chlorocarbonyl)phenyl acetate; Acetylsalicyloyl chloride | 5538-51-2 | C9H7ClO3 | 详情 | 详情 |
| (IV) | 66544 | 2-Amino-5-nitrothiazole;5-Nitro-2-aminothiazole | 121-66-4 | C3H3N3O2S | 详情 | 详情 |