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【结 构 式】 
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【药物名称】KP-136, AL-136 【化学名称】8-Hexyloxy-3-(1H-tetrazol-5-yl)-2H-1-benzopyran-2-one 【CA登记号】76239-32-2 【 分 子 式 】C16H18N4O3 【 分 子 量 】314.34686 |
【开发单位】Kaken (Originator) 【药理作用】Antiallergy/Antiasthmatic Drugs, Asthma Therapy, RESPIRATORY DRUGS, Mediator Release Inhibitors |
合成路线1
The demethylation ot o-vanillin (I) with AlCl3 dissolved in pyridine gives 2,3 dihydroxybenzaldehyde (II). Subsequent alkylation by means of hexyl bromide with NaH gives 3-hexyloxy-2-hydroxybenzaldehyde (III), which is then condensed with malononitrile and piperidine, yielding 3-cyano-8-hexyloxycromen-2-one (IV), a needle-like yellow crystalline substance. Finally, compound (IV) is treated with sodium azide and AlCl3 in refluxing THF, yielding the formation of the tetrazole ring.
| 【1】 Tasaka, K.; KP-136. Drugs Fut 1988, 13, 10, 915. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10158 | Piperidine | 110-89-4 | C5H11N | 详情 | 详情 | |
| 11108 | n-Hexyl bromide; 1-Bromohexane | 111-25-1 | C6H13Br | 详情 | 详情 | |
| (I) | 12620 | o-Vanillin; 2-Hydroxy-3-methoxybenzaldehyde | 148-53-8 | C8H8O3 | 详情 | 详情 |
| (II) | 12380 | 2,3-Dihydroxybenzaldehyde | 24677-78-9 | C7H6O3 | 详情 | 详情 |
| (III) | 23096 | 3-(hexyloxy)-2-hydroxybenzaldehyde | C13H18O3 | 详情 | 详情 | |
| (IV) | 23097 | 8-(hexyloxy)-2-oxo-2H-chromene-3-carbonitrile | C16H17NO3 | 详情 | 详情 |