5-(acryloyloxy)pentyl acrylate; 1,6-Hexanediol Diacrylate -Drug Synthesis Database

【结构式】

【分子编号】15470

【品名】5-(acryloyloxy)pentyl acrylate; 1,6-Hexanediol Diacrylate

【CA登记号】36840-85-4

【分子式】C₁₁H₁₆O₄

【分子量】212.24564

【元素组成】C 62.25% H 7.6% O 30.15%

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：(III)

The reaction of acryloyl chloride (I) with pentane-1,5-diol (II) by means of triethylamine and pyrogalol in hot benzene gives 1,5-pentamethylene diacrylate (III), which is condensed with tetrahydropapaverine (IV) in refluxing benzene to afford N,N'-4,10-dioxa-3,11-dioxotridecylene-1,13-bis(tetrahydropapaverine) (V). Finally, this compound is quaternized by treatment with methyl benzenesulfonate in acetonitrile.

参考文献中间体

合成目标

【1】 Dewar, G.H.; Dhar, N.C.; Sternlake, J.B.; Urwin, R.J.; Waigh, R.D. (Glaxo Wellcome Inc.); Quarternary ammonium compounds. DE 2655883; FR 2334359; JP 52077069; US 4179507 .
【2】 Serradell, M.N.; Blancafort, P.; Castaner, J.; Hillier, K.; Atracurium Besilate. Drugs Fut 1980, 5, 11, 541.

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)	11577	Acryloyl chloride; Acrylyl chloride;2-Propenoyl chloride	814-68-6	C₃H₃ClO	详情	详情
(II)	15471	1,5-pentanediol	111-29-5	C₅H₁₂O₂	详情	详情
(III)	15470	5-(acryloyloxy)pentyl acrylate; 1,6-Hexanediol Diacrylate	36840-85-4	C₁₁H₁₆O₄	详情	详情
(IV)	15468	1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline; 1-(3,4-dimethoxybenzyl)-6-methoxy-1,2,3,4-tetrahydro-7-isoquinolinyl methyl ether		C₂₀H₂₅NO₄	详情	详情
(V)	15473	5-([3-[(1R)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]propanoyl]oxy)pentyl 3-[(1R)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]propanoate		C₅₁H₆₆N₂O₁₂	详情	详情
(VI)	15474	methyl benzenesulfonate	80-18-2	C₇H₈O₃S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(III)

The optical resolution of (±)-tetrahydropapaverine (I) with N-acetyl-L-leucine yields (R)-tetrahydropapaverine (II), which is condensed with 1,5-pentamethylene diacrylate (III) (obtained by esterification of 1,5-pentanediol (IV) with 3-bromopropionic acid by means of p-toluenesulfonic acid followed by dehydromination with triethylamine) in hot glacial acetic acid and treated with oxalic acid to afford the bis-tetrahydropapaverine derivative (VI). Finally, this compound is treated with aqueous Na2CO3 to eliminate the oxalic acid and then treated with methyl benezenesulfonate (VII) at room temperature. The resulting product is a 58:34:6 mixture of the (1R-cis, 1'R-cis)- (1R-cis, 1'R-trans)- and (1R-trans, 1'R-trans)-isomers, which is resolved by column chromatography over silica gel using an 80:20:5 mixture of dichloromethane methanol and methanesulfonic acid.

参考文献中间体

合成目标

【1】 Mealy, N.; Castaner, J.; Cisatracurium Besylate. Drugs Fut 1996, 21, 1, 14.
【2】 Hill, D.A.; Turner, G.L. (Glaxo Wellcome plc); Neuromuscular blocking agents. CH 683427; EP 0539470; FR 2665791; GB 2260763; JP 1993508648; JP 1998139763; US 5453510; WO 9200965 .

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)	15468	1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline; 1-(3,4-dimethoxybenzyl)-6-methoxy-1,2,3,4-tetrahydro-7-isoquinolinyl methyl ether		C₂₀H₂₅NO₄	详情	详情
(II)	15469	(1R)-1-(3,4-dimethoxybenzyl)-6-methoxy-1,2,3,4-tetrahydro-7-isoquinolinyl methyl ether; (1R)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline		C₂₀H₂₅NO₄	详情	详情
(III)	15470	5-(acryloyloxy)pentyl acrylate; 1,6-Hexanediol Diacrylate	36840-85-4	C₁₁H₁₆O₄	详情	详情
(IV)	15471	1,5-pentanediol	111-29-5	C₅H₁₂O₂	详情	详情
(V)	15472	3-Bromopropionic acid	590-92-1	C₃H₅BrO₂	详情	详情
(VI)	15473	5-([3-[(1R)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]propanoyl]oxy)pentyl 3-[(1R)-1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-3,4-dihydro-2(1H)-isoquinolinyl]propanoate		C₅₁H₆₆N₂O₁₂	详情	详情
(VII)	15474	methyl benzenesulfonate	80-18-2	C₇H₈O₃S	详情	详情

Extended Information