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【结 构 式】

【分子编号】56182

【品名】allyl 2-methoxy-5-nitrophenyl ether; 2-(allyloxy)-1-methoxy-4-nitrobenzene

【CA登记号】

【 分 子 式 】C10H11NO4

【 分 子 量 】209.20168

【元素组成】C 57.41% H 5.3% N 6.7% O 30.59%

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)

Alkylation of the sodium salt of 5-nitroguaiacol (I) with allyl bromide (II) gave the allyl ether (III). The methoxy group of (III) was then displaced by NaOH in hot DMSO to produce 2-(allyloxy)-4-nitrophenol (IV), which was further alkylated with (R)-glycidyl tosylate (V), yielding the chiral oxirane (VI). Claisen rearrangement of the allyl ether function of (VI), followed by intramolecular cyclization between the phenol and epoxide groups in hot mesitylene furnished the benzodioxane derivative (VII). Treatment of (VII) with p-toluenesulfonyl chloride afforded tosylate (VIII). Oxidative cleavage of the allyl group of (VIII) with KMnO4 under phase-transfer conditions gave rise to the carboxylic acid (IX). Catalytic hydrogenation of the nitro group of (IX), followed by lactamization of the resultant aminoacid (X) under acidic conditions produced the dioxinoindolone system (XI). Then, nucleophilic displacement of the tosylate group of (XI) with benzylamine (XII) yielded the desired amine, which was finally converted to the corresponding fumarate salt.

1 Stack, G.P.; Mewshaw, R.E.; Bravo, B.A.; Kang, Y.H. (Wyeth); Dioxino derivs. and their use as dopamine agonists. EP 0771800; JP 1997249671; US 5756532 .
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) 56181 sodium 2-methoxy-5-nitrobenzenolate C7H6NNaO4 详情 详情
(II) 11463 3-Bromo-1-propene; 3-Bromopropene;allyl bromide 106-95-6 C3H5Br 详情 详情
(III) 56182 allyl 2-methoxy-5-nitrophenyl ether; 2-(allyloxy)-1-methoxy-4-nitrobenzene C10H11NO4 详情 详情
(IV) 56183 2-(allyloxy)-4-nitrophenol C9H9NO4 详情 详情
(V) 16242 (2R)oxiranylmethyl 4-methylbenzenesulfonate; (2R)-(-)-Glycidyl tosylate 113826-06-5 C10H12O4S 详情 详情
(VI) 56184 (2R)-2-{[2-(allyloxy)-4-nitrophenoxy]methyl}oxirane; allyl 5-nitro-2-[(2R)oxiranylmethoxy]phenyl ether C12H13NO5 详情 详情
(VII) 56185 [(2S)-8-allyl-7-nitro-2,3-dihydro-1,4-benzodioxin-2-yl]methanol C12H13NO5 详情 详情
(VIII) 56186 [(2R)-8-allyl-7-nitro-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate C19H19NO7S 详情 详情
(IX) 56187 2-[(3R)-3-({[(4-methylphenyl)sulfonyl]oxy}methyl)-6-nitro-2,3-dihydro-1,4-benzodioxin-5-yl]acetic acid C18H17NO9S 详情 详情
(X) 56188 2-[(3R)-6-amino-3-({[(4-methylphenyl)sulfonyl]oxy}methyl)-2,3-dihydro-1,4-benzodioxin-5-yl]acetic acid C18H19NO7S 详情 详情
(XI) 56189 [(2R)-8-oxo-2,3,8,9-tetrahydro-7H-[1,4]dioxino[2,3-e]indol-2-yl]methyl 4-methylbenzenesulfonate C18H17NO6S 详情 详情
(XII) 15147 Benzylamine; Phenylmethanamine 100-46-9 C7H9N 详情 详情
Extended Information