6,7-dimethoxy-1H-isochromene-1,3(4H)-dione -Drug Synthesis Database

【结构式】

【分子编号】55162

【品名】6,7-dimethoxy-1H-isochromene-1,3(4H)-dione

【CA登记号】

【分子式】C₁₁H₁₀O₅

【分子量】222.1974

【元素组成】C 59.46% H 4.54% O 36%

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)

Isoquinoline (III) was prepared by the condensation of piperonal N-propylimine (I) with 4,5-dimethoxyhomophthalic anhydride (II). Subsequent intramolecular Friedel-Crafts acylation of (III) in the presence of Eaton's reagent gave rise to the indenoisoquinoline (IV). Reduction of the ketone and lactam functions of (IV) using borane-tetrahydrofuran complex provided alcohol (V). This underwent simultaneous dehydration and dehydrogenation in the presence of Pd/C in refluxing HOAc to afford, after treatment with NaCl, the target indenoisoquinolinium chloride salt.

参考文献中间体

合成目标

【1】 Jayaraman, M.; Fox, B.M.; Hollingshead, M.; Kohlhagen, G.; Pommier, Y.; Cushman, M.; Synthesis of new dihydroindeno[1,2-c]isoquinoline and indenoisoquinolinium chloride topoisomerase I inhibitor having high in vivo anticancer activity in the hollow fiber animal model. J Med Chem 2002, 45, 1, 242.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	55161	N-[(E)-1,3-benzodioxol-5-ylmethylidene]-N-propylamine; N-[(E)-1,3-benzodioxol-5-ylmethylidene]-1-propanamine	C₁₁H₁₃NO₂	详情	详情
(II)	55162	6,7-dimethoxy-1H-isochromene-1,3(4H)-dione	C₁₁H₁₀O₅	详情	详情
(III)	55163	(3S,4R)-3-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-2-propyl-1,2,3,4-tetrahydro-4-isoquinolinecarboxylic acid	C₂₂H₂₃NO₇	详情	详情
(IV)	55164	(6aS,12aR)-2,3-dimethoxy-6-propyl-6a,12a-dihydro-5H-[1,3]dioxolo[4',5':5,6]indeno[1,2-c]isoquinoline-5,12(6H)-dione	C₂₂H₂₁NO₆	详情	详情
(V)	55165	(6aS,12R,12aR)-2,3-dimethoxy-6-propyl-6,6a,12,12a-tetrahydro-5H-[1,3]dioxolo[4',5':5,6]indeno[1,2-c]isoquinolin-12-ol	C₂₂H₂₅NO₅	详情	详情

Extended Information