methyl 8-(4-formylphenoxy)octanoate -Drug Synthesis Database

【结构式】

【分子编号】53131

【品名】methyl 8-(4-formylphenoxy)octanoate

【CA登记号】n/a

【分子式】C₁₆H₂₂O₄

【分子量】278.34828

【元素组成】C 69.04% H 7.97% O 22.99%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(IX)

The intermediate aldehyde (IX) was synthesized by alkylation of the sodium salt of 4-hydroxybenzaldehyde (VII) with methyl 8-bromooctanoate (VIII).

参考文献中间体

合成目标

【1】 Folkes, A.; et al.; Synthesis and in vitro evaluation of a series of diketopiperazine inhibitors of plasminogen activator inhibitor-1. Bioorg Med Chem Lett 2001, 11, 19, 2589.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VII)	13433	4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde	123-08-0	C₇H₆O₂	详情	详情
(VIII)	53130	methyl 8-bromooctanoate	26825-92-3	C₉H₁₇BrO₂	详情	详情
(IX)	53131	methyl 8-(4-formylphenoxy)octanoate	n/a	C₁₆H₂₂O₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IX)

Dioxopiperazine (X) was diacetylated in refluxing acetic anhydride to yield (XI). Aldol condensation of (XI) with the precursor aldehyde (VI) using potassium tert-butoxide in THF gave the mono-arylidene piperazine (XII). Further condensation of (XII) with the intermediate aldehyde (IX) in the presence of Cs2CO3 in DMF furnished the deacetylated bis-arylidene piperazine (XIII). The methyl ester group of (XIII) was finally hydrolyzed to the title carboxylic acid using NaOH in H2O/MeOH/THF.

参考文献中间体

合成目标

【1】 Folkes, A.; et al.; Synthesis and in vitro evaluation of a series of diketopiperazine inhibitors of plasminogen activator inhibitor-1. Bioorg Med Chem Lett 2001, 11, 19, 2589.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VI)	53129	N-(4-formylphenyl)-2-thiophenecarboxamide	n/a	C₁₂H₉NO₂S	详情	详情
(IX)	53131	methyl 8-(4-formylphenoxy)octanoate	n/a	C₁₆H₂₂O₄	详情	详情
(X)	29800	2,5-piperazinedione；2,5-diketopiperazine;cycloglycylglycine；2,5-dioxopiperazine;cyclodiglycine;cyclo(glycylglycyl)	106-57-0	C₄H₆N₂O₂	详情	详情
(XI)	19188	1,4-diacetyl-2,5-piperazinedione;N,N'-DIACETYLGLYCINE ANHYDRIDE;1,4-DIACETYL-PIPERAZINE-2,5-DIONE;1,4-DIACETYLTETRAHYDRO-2,5-PYRAZINEDIONE;1,4-DIACETYL-2,5-DIKETOPIPERAZINE;1,4-DIACETYL-2,5-DIOXOPIPERAZINE	3027-05-2	C₈H₁₀N₂O₄	详情	详情
(XII)	53132	N-{4-[(4-acetyl-3,6-dioxo-2-piperazinylidene)methyl]phenyl}-2-thiophenecarboxamide	n/a	C₁₈H₁₅N₃O₄S	详情	详情
(XIII)	53133	methyl 8-(4-{[3,6-dioxo-5-((Z)-{4-[(2-thienylcarbonyl)amino]phenyl}methylidene)-2-piperazinylidene]methyl}phenoxy)octanoate	n/a	C₃₂H₃₃N₃O₆S	详情	详情

Extended Information