2-[(E)-4-(1,3-benzodioxol-5-yl)-3-butenyl]-1H-isoindole-1,3(2H)-dione -Drug Synthesis Database

【结构式】

【分子编号】24414

【品名】2-[(E)-4-(1,3-benzodioxol-5-yl)-3-butenyl]-1H-isoindole-1,3(2H)-dione

【CA登记号】

【分子式】C₁₉H₁₅NO₄

【分子量】321.33244

【元素组成】C 71.02% H 4.71% N 4.36% O 19.92%

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：(VI)

6-Fluoro-8-hydroxychroman-4-one (I) was converted to ethylene ketal (II) upon treatment with ethylene glycol and triethyl orthoformate, and subsequently alkylated with 1,2-dibromoethane under phase-transfer conditions to afford the bromoethyl ether (III). Wittig condensation of piperonal (V) with the (3-phthalimidopropyl)phosphonium salt (IV) in the presence of NaOMe in dioxan provided olefin (VI), which was hydrogenated over Pd/C to furnish the arylbutyl phthalimide (VII). Further deprotection of the phthalimido group of (VII) with CH3NH2 gave amine (VIII). Then, alkylation of (VIII) with bromide (III), followed by acid hydrolysis of the ketal function yielded the title compound.

参考文献中间体

合成目标

【1】 Yasunaga, T.; Wanibuchi, F.; Yamaguchi, T.; Yamashita, H.; Kontani, T.; Tsukamoto, S.; Nomura, T.; Naito, R.; Kimura, T.; Mase, T.; Synthesis and pharmacological characterization of novel 6-fluorochroman derivatives as potential 5-HT1A receptor antagonists. J Med Chem 1998, 41, 15, 2765.

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)	24409	6-fluoro-8-hydroxy-2,3-dihydro-4H-chromen-4-one		C₉H₇FO₃	详情	详情
(II)	24410	6-Fluoro-3,4-dihydro-2H-spiro[1-benzopyran-4,2'-1,3-dioxolan]-8-ol		C₁₁H₁₁FO₄	详情	详情
(III)	24411	8-(2-Bromoethoxy)-6-fluoro-3,4-dihydro-2H-spiro[1-benzopyran-4,2'-1,3-dioxolane]		C₁₃H₁₄BrFO₄	详情	详情
(IV)	24412	[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl](triphenyl)phosphonium bromide		C₂₉H₂₅BrNO₂P	详情	详情
(V)	10127	1,3-Benzodioxole-5-carbaldehyde; Heliotropine	120-57-0	C₈H₆O₃	详情	详情
(VI)	24414	2-[(E)-4-(1,3-benzodioxol-5-yl)-3-butenyl]-1H-isoindole-1,3(2H)-dione		C₁₉H₁₅NO₄	详情	详情
(VII)	24415	2-[4-(1,3-benzodioxol-5-yl)butyl]-1H-isoindole-1,3(2H)-dione		C₁₉H₁₇NO₄	详情	详情
(VIII)	24416	4-(1,3-benzodioxol-5-yl)-1-butanamine		C₁₁H₁₅NO₂	详情	详情

Extended Information