10-(1,3-benzodioxol-5-yl)furo[3',4':6,7]naphtho[1,2-d][1,3]dioxole-7,9-dione -Drug Synthesis Database

【结构式】

【分子编号】46640

【品名】10-(1,3-benzodioxol-5-yl)furo[3',4':6,7]naphtho[1,2-d][1,3]dioxole-7,9-dione

【CA登记号】

【分子式】C₂₀H₁₀O₇

【分子量】362.2952

【元素组成】C 66.31% H 2.78% O 30.91%

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：(XII)

Alternatively, the condensation of 1,3-benzodioxole-5-carbaldehyde ethylene ketal (VIII) with carbaldehyde (V) by means of n-BuLi gives the hydroxy ketal (IX), which is treated with Ac2O, HOAc and maleic anhydride (XI) at 140 C to perform a Diels-Alder cyclization between the nonisolated isobenzofuran (X) (a reactive diene) and the maleic anhydride (the dienophile), giving rise to the cyclic anhydride (XII). Finally, this compound is reduced with NaBH4 to the target compound along with some structural isomer (XIII) that is separated by chromatography.

参考文献中间体

合成目标

【1】 Urasaki, Y.; et al.; Activity of a novel camptothecin analogue, homocamptothecin, in camptothecin-resistant cell lines with topoisomerase I alterations. Cancer Res 2000, 60, 23, 6577.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV)	10127	1,3-Benzodioxole-5-carbaldehyde; Heliotropine	120-57-0	C₈H₆O₃	详情	详情
(VIII)	46637	5-(1,3-dioxolan-2-yl)-1,3-benzodioxole		C₁₀H₁₀O₄	详情	详情
(IX)	46638	1,3-benzodioxol-5-yl[5-(1,3-dioxolan-2-yl)-1,3-benzodioxol-4-yl]methanol		C₁₈H₁₆O₇	详情	详情
(X)	46639	8-(1,3-benzodioxol-5-yl)furo[3,4-e][1,3]benzodioxole		C₁₆H₁₀O₅	详情	详情
(XI)	11182	2,5-Furandione; Maleic anhydride	108-31-6	C₄H₂O₃	详情	详情
(XII)	46640	10-(1,3-benzodioxol-5-yl)furo[3',4':6,7]naphtho[1,2-d][1,3]dioxole-7,9-dione		C₂₀H₁₀O₇	详情	详情
(XIII)	46641	10-(1,3-benzodioxol-5-yl)furo[3',4':6,7]naphtho[1,2-d][1,3]dioxol-9(7H)-one		C₂₀H₁₂O₆	详情	详情

Extended Information