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【结 构 式】 
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【分子编号】46608 【品名】7-(benzyloxy)-3-(hydroxymethyl)-3-(methylsulfinyl)-2,3-dihydro-4H-chromen-4-one 【CA登记号】 |
【 分 子 式 】C18H18O5S 【 分 子 量 】346.40392 【元素组成】C 62.41% H 5.24% O 23.09% S 9.26% |
合成路线1
该中间体在本合成路线中的序号：(X)Methyl 2,4-dihydroxybenzoate (VII) was selectively protected as the 4-benzyl ether (VIII) with benzyl bromide in the presence of potassium carbonate. Condensation with sodium (methylsulfinyl)methyde provided the corresponding methylsulfinyl ketone (IX). This was condensed with two equivalents of formaldehyde to yield (X). Subsequent pyrolysis of the sulfoxide group furnished chromenone (XI). Deprotection of the benzyl ether was achieved by treatment with boron trichloride, and the resulting 7-hydroxychromenone (XII) was then alkylated with 1-bromo-3-chloropropane (II) to give 7-(3-chloropropoxy)-3-(hydroxymethyl)-4H-chromen-4-one (V).
| 【1】 Nieto, J.; Bolos, J.; Unpublished results . |
| 【2】 Princep, M.; Guglietta, A.; Bolos, J.; Abaperidone Hydrochloride. Drugs Fut 2001, 26, 4, 335. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (II) | 10358 | 1-Bromo-3-chloropropane | 109-70-6 | C3H6BrCl | 详情 | 详情 |
| (V) | 26822 | 7-(3-chloropropoxy)-3-(hydroxymethyl)-4H-chromen-4-one | C13H13ClO4 | 详情 | 详情 | |
| (VII) | 16623 | methyl 2,4-dihydroxybenzoate | 2150-47-2 | C8H8O4 | 详情 | 详情 |
| (VIII) | 46606 | methyl 4-(benzyloxy)-2-hydroxybenzoate | C15H14O4 | 详情 | 详情 | |
| (IX) | 46607 | 1-[4-(benzyloxy)-2-hydroxyphenyl]-2-(methylsulfinyl)-1-ethanone | C16H16O4S | 详情 | 详情 | |
| (X) | 46608 | 7-(benzyloxy)-3-(hydroxymethyl)-3-(methylsulfinyl)-2,3-dihydro-4H-chromen-4-one | C18H18O5S | 详情 | 详情 | |
| (XI) | 46609 | 7-(benzyloxy)-3-(hydroxymethyl)-4H-chromen-4-one | C17H14O4 | 详情 | 详情 | |
| (XII) | 46610 | 7-hydroxy-3-(hydroxymethyl)-4H-chromen-4-one | C10H8O4 | 详情 | 详情 |