4-PENTENOYL CHLORIDE -Drug Synthesis Database

【结构式】

【分子编号】61648

【品名】4-PENTENOYL CHLORIDE

【CA登记号】

【分子式】C₅H₇ClO

【分子量】118.56268

【元素组成】C 50.65% H 5.95% Cl 29.9% O 13.49%

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：(VII)

Treatment of methyl 3-hydroxy-8-oxabicyclo[3.2.1]oct-2-ene-2-carboxylate (I) with N-phenyl trifluoromethanesulfonimide leads to the vinyl triflate (II). Suzuki coupling of triflate (II) with 3,4-dichlorophenylboronic acid (III) furnishes the oxabicyclooctene adduct (IV), which is further reduced to the oxabicyclooctane (V) with SmI2. Ester reduction in (V) with LiAlH4 provides alcohol (VI). This is finally esterified with 4-pentenoyl chloride (VII) to furnish the title compound.

参考文献中间体

合成目标

【1】 Meltzer, P.C.; Liu, S.; Blanchette, H.; Blundell, P.; Madras, B.; Design and synthesis of an irreversible dopamine-sparing cocaine antagonist. Bioorg Med Chem 2002, 10, 11, 3583.

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)	61643	methyl (1R,5S)-3-hydroxy-8-oxabicyclo[3.2.1]oct-2-ene-2-carboxylate		C₉H₁₂O₄	详情	详情
(II)	61644	methyl (1R,5S)-3-{[(trifluoromethyl)sulfonyl]oxy}-8-oxabicyclo[3.2.1]oct-2-ene-2-carboxylate		C₁₀H₁₁F₃O₆S	详情	详情
(III)	34040	3,4-Dichlorophenylboronic acid	151169-75-4	C₆H₅BCl₂O₂	详情	详情
(IV)	61645	methyl (1R,5S)-3-(3,4-dichlorophenyl)-8-oxabicyclo[3.2.1]oct-2-ene-2-carboxylate		C₁₅H₁₄Cl₂O₃	详情	详情
(V)	61646	methyl (1R,2S,3R,5S)-3-(3,4-dichlorophenyl)-8-oxabicyclo[3.2.1]octane-2-carboxylate		C₁₅H₁₆Cl₂O₃	详情	详情
(VI)	61647	[(1R,2R,3R,5S)-3-(3,4-dichlorophenyl)-8-oxabicyclo[3.2.1]oct-2-yl]methanol		C₁₄H₁₆Cl₂O₂	详情	详情
(VII)	61648	4-PENTENOYL CHLORIDE		C₅H₇ClO	详情	详情

合成路线2

该中间体在本合成路线中的序号：

Dihydroxylation of the benzo[b]pyrano[3,2-h]acridinone derivative (I) by means of N-methylmorpholine-N-oxide in the presence of OsO4 leads to the cis-diol (II), which upon esterification with 4-pentenoyl chloride in pyridine furnishes a mixture of diester (III) and the title mono-pentenoate ester, which can be separated employing flash chromatography.

参考文献中间体

合成目标

【1】 Mai, H.D.T.; Gaslonde, T.; Michel, S.; Tillequin, F.; Koch, M.; Bongui, J.-B.; Elomri, A.; Seguin, E.; Pfeiffer, B.; Renard, P.; David-Cordonnier, M.-H.; Laine, W.; Bailly C.; Kraus-Berthier, L.; Leonce, S.; Hickman, J.A.; Pierre, A.; Structure-activity relationships and mechanism of action of antitumor benzo[b]pyrano[3,2-h]acridin-7-one acronycine analogues. J Med Chem 2003, 46, 14, 3072.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
	61648	4-PENTENOYL CHLORIDE	C₅H₇ClO	详情	详情
(I)	47435	6-methoxy-3,3,14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one	C₂₄H₂₁NO₃	详情	详情
(II)	47436	(1S,2S)-1,2-dihydroxy-6-methoxy-3,3,14-trimethyl-1,2,3,14-tetrahydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one	C₂₄H₂₃NO₅	详情	详情
(III)	64870	3,3,14-trimethyl-6-(methyloxy)-7-oxo-1-(4-pentenoyloxy)-2,3,7,14-tetrahydro-1H-benzo[b]pyrano[3,2-h]acridin-2-yl 4-pentenoate	C₃₄H₃₅NO₇	详情	详情

Extended Information