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【结 构 式】 
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【分子编号】35854 【品名】1-(5,8-dimethyl-2-naphthyl)-2-propen-1-one 【CA登记号】 |
【 分 子 式 】C15H14O 【 分 子 量 】210.27556 【元素组成】C 85.68% H 6.71% O 7.61% |
合成路线1
该中间体在本合成路线中的序号：(III)This compound has been obtained by two related ways: 1) The Grignard reaction of 5,8-dimethylnaphthalene-2-carbaldehyde (I) with vinylmagnesium bromide in ether/THF gives the expected carbinol (II), which is oxidized with MnO2 in dichloromethane yielding the propenone (III). The condensation of (III) with 4-formylbenzoic acid methyl ester (IV) by means of 3-benzyl-5-(hydroxymethyl)-4-methylthiazolium chloride (BHMT) in refluxing ethanol affords the 1,4-butanedione (V), which is cyclized with ammonium acetate in refluxing methanol to give the substituted pyrrole (VI). Finally, the ester group of (V) is hydrolyzed with NaOH in refluxing ethanol/water. 2) 1,4-Butanedione (V) can also be obtained by condensation of 5,8-dimethylnaphthalene-2-carbaldehyde (I) with 4-acryloylbenzoic acid methyl ester (VII) by means of BHMT in hot DMF.
| 【1】 Tagami, K.; Yoshimura, H.; Nagai, M.; Hibi, S.; Kikuchi, K.; Sato, T.; Okita, M.; Okamoto, Y.; Nagasaka, Y.; Kobayashi, N.; Hida, T.; Tai, K.; Tokuhara, N.; Kobayashi, S. (Eisai Co., Ltd.); Fused-ring carboxylic acid derivs.. EP 0889032; US 6110959; US 6121309; WO 9734869 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 16524 | bromo(vinyl)magnesium | 1826-67-1 | C2H3BrMg | 详情 | 详情 | |
| (I) | 35852 | 5,8-dimethyl-2-naphthaldehyde | C13H12O | 详情 | 详情 | |
| (II) | 35853 | 1-(5,8-dimethyl-2-naphthyl)-2-propen-1-ol | C15H16O | 详情 | 详情 | |
| (III) | 35854 | 1-(5,8-dimethyl-2-naphthyl)-2-propen-1-one | C15H14O | 详情 | 详情 | |
| (IV) | 10170 | methyl 4-formylbenzoate | 1571-08-0 | C9H8O3 | 详情 | 详情 |
| (V) | 35855 | methyl 4-[4-(5,8-dimethyl-2-naphthyl)-4-oxobutanoyl]benzoate | C24H22O4 | 详情 | 详情 | |
| (VI) | 35856 | methyl 4-[5-(5,8-dimethyl-2-naphthyl)-1H-pyrrol-2-yl]benzoate | C24H21NO2 | 详情 | 详情 | |
| (VII) | 35857 | methyl 4-acryloylbenzoate | C11H10O3 | 详情 | 详情 |