benzyl 3-[(E)-2-nitroethenyl]phenyl ether; 1-(benzyloxy)-3-[(E)-2-nitroethenyl]benzene -Drug Synthesis Database

【结构式】

【分子编号】38829

【品名】benzyl 3-[(E)-2-nitroethenyl]phenyl ether; 1-(benzyloxy)-3-[(E)-2-nitroethenyl]benzene

【CA登记号】

【分子式】C₁₅H₁₃NO₃

【分子量】255.27316

【元素组成】C 70.58% H 5.13% N 5.49% O 18.8%

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：(III)

Acid chloride (II) was prepared by treatment of 3,5-diiodo-4-methoxyphenylacetic acid with oxalyl chloride (1). Coupling of (II) with amine (IV), obtained by reducing its nitro precursor (III) with LiAlH4, under Schotten-Baumann conditions furnished amide (V). Bischler-Napieralski cyclization of amide (V), followed by NaBH4 reduction of the intermediate dihydroisoquinoline yielded tetrahydroisoquinoline (VI). Finally, deprotection of the benzyl ether of (VI) by refluxing in the presence of HCl provided the title compound.

参考文献中间体

合成目标

【1】 Shams, G.; Feller, D.R.; Zheng, W.; Konkar, A.A.; Miller, D.D.; Nikulin, V.I.; Vansal, S.S.; 2-Amino-4-benzyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridines: Novel selective beta3-adrenoceptor agonists. J Med Chem 1999, 42, 12, 2287.
【2】 Feller, D.R.; Miller, D.D.; He, Y.; Vansal, S.S.; Nikulin, V.I.; Synthesis and human beta-adrenoceptor activity of 1-(3,5-diiodo-4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinolin-6-ol derivatives in vitro. J Med Chem 2000, 43, 4, 591.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	35234	2-(3,5-diiodo-4-methoxyphenyl)acetic acid	C₉H₈I₂O₃	详情	详情
(II)	35235	2-(3,5-diiodo-4-methoxyphenyl)acetyl chloride	C₉H₇ClI₂O₂	详情	详情
(III)	38829	benzyl 3-[(E)-2-nitroethenyl]phenyl ether; 1-(benzyloxy)-3-[(E)-2-nitroethenyl]benzene	C₁₅H₁₃NO₃	详情	详情
(IV)	38830	3-(benzyloxy)phenethylamine; 2-[3-(benzyloxy)phenyl]-1-ethanamine	C₁₅H₁₇NO	详情	详情
(V)	38831	N-[3-(benzyloxy)phenethyl]-2-(3,5-diiodo-4-methoxyphenyl)acetamide	C₂₄H₂₃I₂NO₃	详情	详情
(VI)	38832	6-(benzyloxy)-1-(3,5-diiodo-4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinoline; benzyl 1-(3,5-diiodo-4-methoxybenzyl)-1,2,3,4-tetrahydro-6-isoquinolinyl ether	C₂₄H₂₃I₂NO₂	详情	详情

Extended Information