5-(hydroxymethyl)-1,3-cyclohexanedione -Drug Synthesis Database

【结构式】

【分子编号】47758

【品名】5-(hydroxymethyl)-1,3-cyclohexanedione

【CA登记号】

【分子式】C₇H₁₀O₃

【分子量】142.1546

【元素组成】C 59.14% H 7.09% O 33.76%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(II)

Acidic hydrolysis of the enol ether groups of 1,4-dihydro-3,5-dimethoxybenzyl alcohol (I) gave diketone (II). Subsequent condensation of (II) with chloroacetaldehyde in the presence of NaHCO3, followed by dehydration of the intermediate (III) upon acidic treatment, yielded the tetrahydrobenzofuranone (IV). Tosylate (V) was then prepared by reaction of alcohol (IV) with p-toluenesulfonyl chloride in cold pyridine. Finally, nucleophilic displacement of the tosylate group with benzisoxazolylpiperidine (VI) in N-methylpyrrolidone provided the title amine.

参考文献中间体

合成目标

【1】 Casariego, I.; et al.; New CNS agent precursors. A simple and efficient route for synthesis of 6-aminomethyl-4,5,6,7-tetrahydrobenzofuran-4-ones as conformationally constrained butyrophenone analogues. Tetrahedron Lett 1997, 38, 31, 5555.
【2】 Masaguer, C.F.; Casariego, I.; Raviña, E.; et al.; Conformationally constrained butyrophenones with affinity for dopamine (D1, D2, D4) and serotonin (5-HT2A, 5-HT2C) receptors: Synthesis of aminomethylbenzo[b]furanones and their evaluation as antipsychotics. J Med Chem 2000, 43, 24, 4678.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	25566	(3,5-dimethoxy-2,5-cyclohexadien-1-yl)methanol	C₉H₁₄O₃	详情	详情
(II)	47758	5-(hydroxymethyl)-1,3-cyclohexanedione	C₇H₁₀O₃	详情	详情
(III)	47759	2-[4-(hydroxymethyl)-2,6-dioxocyclohexyl]acetaldehyde	C₉H₁₂O₄	详情	详情
(IV)	47760	6-(hydroxymethyl)-6,7-dihydro-1-benzofuran-4(5H)-one	C₉H₁₀O₃	详情	详情
(V)	47761	(4-oxo-4,5,6,7-tetrahydro-1-benzofuran-6-yl)methyl 4-methylbenzenesulfonate	C₁₆H₁₆O₅S	详情	详情
(VI)	17910	6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole	C₁₂H₁₃FN₂O	详情	详情

Extended Information