(E)-2-heptenal -Drug Synthesis Database

【结构式】

【分子编号】65170

【品名】(E)-2-heptenal

【CA登记号】18829-55-5

【分子式】C₇H₁₂O

【分子量】112.17168

【元素组成】C 74.95% H 10.78% O 14.26%

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：　

The condensation of (3R,4S,6S,9aS)-3-(methoxymethoxy)-4-methyl-6-(phenylsulfonylmethyl)perhydroquinolizine (I) with trans-2-heptenal, followed by a treatment wit Na/Hg gives the 1,3-octadienyl-perhydroquinolizine (II), which is deprotected with HCl in refluxing methanol yielding the alcohol (III). Finally this compound is acetylated with acetic anhydride and pyridine to afford the target (-)-pictamine.

参考文献中间体

合成目标

【1】 Toyooka, N.; Nemoto, H.; Application of chiral building blocks to the synthesis of drugs. Drugs Fut 2002, 27, 2, 143.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	65170	(E)-2-heptenal	18829-55-5	C₇H₁₂O	详情	详情
(I)	51726	[(4S,6S,7R,9aS)-7-(methoxymethoxy)-6-methyloctahydro-2H-quinolizin-4-yl]methyl phenyl sulfone; (3R,4S,6S,9aS)-3-(methoxymethoxy)-4-methyl-6-[(phenylsulfonyl)methyl]octahydro-2H-quinolizine		C₁₉H₂₉NO₄S	详情	详情
(II)	51727	(3R,4S,6S,9aS)-3-(methoxymethoxy)-4-methyl-6-[(1E,3E)-1,3-octadienyl]octahydro-2H-quinolizine; (3R,4S,6S,9aS)-4-methyl-6-[(1E,3E)-1,3-octadienyl]octahydro-2H-quinolizin-3-yl methoxymethyl ether		C₂₀H₃₅NO₂	详情	详情
(III)	51728	(3R,4S,6S,9aS)-4-methyl-6-[(1E,3E)-1,3-octadienyl]octahydro-2H-quinolizin-3-ol		C₁₈H₃₁NO	详情	详情

合成路线2

该中间体在本合成路线中的序号：　

The condensation of the chiral octahydroquinoline (I) with phenyl(phenylsulfanylmethyl)sulfone by means of BuLi in THF gives the perhydroquinoline adduct (II), which is treated with Bu3SnH and AIBN in refluxing benzene to yield the phenylsulfonylmethyl derivative (III). The reduction of the ketonic group of (III) with NaBH4, followed by elimination of the resulting OH group by reaction with thiocarbonyldiimidazole and then with Bu3SnH in refluxing benzene affords the chiral perhydroquinoline-1-carboxylic acid methyl ester derivative (IV). Decarboxylation of (IV) by means of Pr-S-Li in THF/HMPA, followed by reprotection with Boc2O in refluxing benzene provides the chiral tert-butyl carbamate (V), which is condensed with trans-2-heptenal by means of BuLi in THF and then treated with Na/Hg in methanol to give the 5-(1,3-octadienyl) derivative (VI). Finally compound (VI) is decarboxylated by means of HCl in refluxing methanol o afford the target lepadin B.

参考文献中间体

合成目标

【1】 Toyooka, N.; Nemoto, H.; Application of chiral building blocks to the synthesis of drugs. Drugs Fut 2002, 27, 2, 143.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	65170	(E)-2-heptenal	18829-55-5	C₇H₁₂O	详情	详情
(I)	51773	methyl (2S,3S,4aS,8aR)-3-(methoxymethoxy)-2-methyl-7-oxo-3,4,4a,7,8,8a-hexahydro-1(2H)-quinolinecarboxylate		C₁₄H₂₁NO₅	详情	详情
(II)	51774	methyl (2S,3S,4aS,8aR)-3-(methoxymethoxy)-2-methyl-7-oxo-5-[(phenylsulfanyl)(phenylsulfonyl)methyl]octahydro-1(2H)-quinolinecarboxylate		C₂₇H₃₃NO₇S₂	详情	详情
(III)	51775	methyl (2S,3S,4aS,5R,8aR)-3-(methoxymethoxy)-2-methyl-7-oxo-5-[(phenylsulfonyl)methyl]octahydro-1(2H)-quinolinecarboxylate		C₂₁H₂₉NO₇S	详情	详情
(IV)	51776	methyl (2S,3S,4aS,5R,8aR)-3-(methoxymethoxy)-2-methyl-5-[(phenylsulfonyl)methyl]octahydro-1(2H)-quinolinecarboxylate		C₂₁H₃₁NO₆S	详情	详情
(V)	51777	tert-butyl (2S,3S,4aS,5R,8aR)-3-(methoxymethoxy)-2-methyl-5-[(phenylsulfonyl)methyl]octahydro-1(2H)-quinolinecarboxylate		C₂₄H₃₇NO₆S	详情	详情
(VI)	51778	tert-butyl (2S,3S,4aS,5S,8aR)-3-(methoxymethoxy)-2-methyl-5-[(1E,3E)-1,3-octadienyl]octahydro-1(2H)-quinolinecarboxylate		C₂₅H₄₃NO₄	详情	详情

Extended Information