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【结 构 式】 
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【分子编号】46784 【品名】6-benzhydryl-2-[[(2S)-5-hydroxy-1,2,3,4-tetrahydro-2-naphthalenyl]methyl]-1,6-dihydro-3(2H)-pyridazinone 【CA登记号】 |
【 分 子 式 】C28H28N2O2 【 分 子 量 】424.5426 【元素组成】C 79.22% H 6.65% N 6.6% O 7.54% |
合成路线1
该中间体在本合成路线中的序号：(XII)Dehydroxylation of compound (I) by hydrogenation over Pd/C in MeOH provides tetralinecarboxylic acid methyl ester (II), which is then reduced by means of LiAlH4 in THF to afford tetralinemethanol as a mixture of enantiomers (III). Separation of isomers in (III) is then achieved by first acylation of the alcohol with (-)-menthyl chloroformate (IV) in pyridine, followed by the separation of the two resulting diastereomers by recrystallization to give (-)-menthyl carbonate (V) and its subsequent hydrolysis with NaOH in THF/H2O to furnish compound (VI).
| 【1】 Tsubaki, K.; Hattori, K.; Tabuchi, S.; Okitsu, O.; Sakane, K.; Tanaka, H.; Taniguchi, K.; A novel pyridazinone derivative as a nonprostanoid PGI2 agonist. Bioorg Med Chem Lett 2000, 10, 24, 2787. |
| 【2】 Taniguchi, K.; Nagano, M.; Hattori, K.; Tsubaki, K.; Okitsu, O.; Tabuchi, S. (Fujisawa Pharmaceutical Co., Ltd.); Naphthalene derivs. as prostaglandin I2 agonists. EP 0749424; JP 1997509958; US 5763489; WO 9524393 . |
| 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) | 46774 | methyl (1R,2S)-1-hydroxy-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenecarboxylate | C13H16O4 | 详情 | 详情 | |
| (II) | 46775 | methyl (2S)-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenecarboxylate | C13H16O3 | 详情 | 详情 | |
| (III) | 46776 | (5-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl)methanol | C12H16O2 | 详情 | 详情 | |
| (IV) | 46777 | (1S,2R,4R)-2-[(chlorocarbonyl)oxy]-1-isopropyl-4-methylcyclohexane | 14602-86-9 | C11H19ClO2 | 详情 | 详情 |
| (V) | 46778 | (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl [(2S)-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl]methyl carbonate | C23H34O4 | 详情 | 详情 | |
| (VI) | 46779 | [(2S)-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl]methanol | C12H16O2 | 详情 | 详情 | |
| (VII) | 46780 | 1,1-diphenylacetone | 781-35-1 | C15H14O | 详情 | 详情 |
| (VIII) | 15618 | 2-Oxoacetic acid; Glyoxylic Acid | 298-12-4 | C2H2O3 | 详情 | 详情 |
| (IX) | 46781 | 2-hydroxy-4-oxo-5,5-diphenylpentanoic acid | C17H16O4 | 详情 | 详情 | |
| (X) | 46782 | 6-benzhydryl-1,6-dihydro-3(2H)-pyridazinone | C17H16N2O | 详情 | 详情 | |
| (XI) | 46783 | 6-benzhydryl-2-[[(2S)-5-methoxy-1,2,3,4-tetrahydro-2-naphthalenyl]methyl]-1,6-dihydro-3(2H)-pyridazinone | C29H30N2O2 | 详情 | 详情 | |
| (XII) | 46784 | 6-benzhydryl-2-[[(2S)-5-hydroxy-1,2,3,4-tetrahydro-2-naphthalenyl]methyl]-1,6-dihydro-3(2H)-pyridazinone | C28H28N2O2 | 详情 | 详情 | |
| (XIII) | 16640 | Ethyl 2-bromoacetate; Ethyl bromoacetate | 105-36-2 | C4H7BrO2 | 详情 | 详情 |
| (XIV) | 46785 | ethyl 2-[((6S)-6-[[3-benzhydryl-6-oxo-3,6-dihydro-1(2H)-pyridazinyl]methyl]-5,6,7,8-tetrahydro-1-naphthalenyl)oxy]acetate | C32H34N2O4 | 详情 | 详情 |