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【结 构 式】

【分子编号】52234

【品名】sodium (Z)-2-[3-(benzyloxy)-4-methoxyphenyl]-2-cyano-1-ethenolate

【CA登记号】

【 分 子 式 】C17H14NNaO3

【 分 子 量 】303.292868

【元素组成】C 67.32% H 4.65% N 4.62% Na 7.58% O 15.83%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(XIX)

In an alternative procedure, isovanillin (XI) was protected by O-benzylation, giving (XII), and its aldehyde group was subsequently reduced to alcohol (XIII) with NaBH4. The benzylic alcohol (XIII) was chlorinated to (XIV), which was converted to nitrile (XV) by chloride displacement with tetraethylammonium cyanide. Nitrile (XV) was subjected to Claisen condensation with ethyl formate, yielding (XVI), followed by sulfonylation with benzenesulfonyl chloride to afford (XVII), which was cyclized to the amino thiophene (XVIII) by treatment with ethyl thioglycolate (IV) as above. Condensation of (XVIII) with 2,5-dimethoxytetrahydrofuran (VI) produced the corresponding pyrrole derivative (XIX). After conversion of the ester group of (XIX) to amide (XX) upon heating with pyrrolidine (VIII), its cyclization with POCl3 furnished the thienopyrrolizinone (XXI). The O-benzyl protecting group of (XXI) was finally cleaved by treatment with HBr in HOAc.

1 Lisowski, V.; et al.; Design, synthesis and antiproliferative activity of tripentones: A new series of antitubulin agents. Bioorg Med Chem Lett 2001, 11, 16, 2205.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 18838 methyl 2-sulfanylacetate 2365-48-2 C3H6O2S 详情 详情
(VI) 12121 (Z)-4-(Dimethylamino)-3-imidazo[1,2-a]pyridin-6-yl-3-buten-2-one C13H15N3O 详情 详情
(VIII) 11376 Pyrrolidine 123-75-1 C4H9N 详情 详情
(XI) 18455 3-hydroxy-4-methoxybenzaldehyde; Isovanillin 621-59-0 C8H8O3 详情 详情
(XII) 10966 3-(Benzyloxy)-4-methoxybenzaldehyde; 3-Benzyloxy-4-methoxybenzaldehyde 6346-05-0 C15H14O3 详情 详情
(XIII) 23823 5-[4-hydroxy-2-(3-hydroxybutyl)-3,5,6-trimethylphenoxy]-2,2-dimethylpentanoic acid C20H32O5 详情 详情
(XIV) 52232 benzyl 5-(chloromethyl)-2-methoxyphenyl ether; 2-(benzyloxy)-4-(chloromethyl)-1-methoxybenzene C15H15ClO2 详情 详情
(XV) 52233 (3-Benzyloxy-4-methoxyphenyl)acetonitrile C16H15NO2 详情 详情
(XVI) 52234 sodium (Z)-2-[3-(benzyloxy)-4-methoxyphenyl]-2-cyano-1-ethenolate C17H14NNaO3 详情 详情
(XVII) 52235 (Z)-2-[3-(benzyloxy)-4-methoxyphenyl]-2-cyanoethenyl benzenesulfonate C23H19NO5S 详情 详情
(XVIII) 52236 methyl 3-amino-4-[3-(benzyloxy)-4-methoxyphenyl]-2-thiophenecarboxylate C20H19NO4S 详情 详情
(XIX) 52234 sodium (Z)-2-[3-(benzyloxy)-4-methoxyphenyl]-2-cyano-1-ethenolate C17H14NNaO3 详情 详情
(XX) 52238 [4-[3-(benzyloxy)-4-methoxyphenyl]-3-(1H-pyrrol-1-yl)-2-thienyl](1-pyrrolidinyl)methanone C27H26N2O3S 详情 详情
(XXI) 52239 3-[3-(benzyloxy)-4-methoxyphenyl]-8H-thieno[2,3-b]pyrrolizin-8-one C23H17NO3S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(XVI)

In an alternative procedure, isovanillin (XI) was protected by O-benzylation, giving (XII), and its aldehyde group was subsequently reduced to alcohol (XIII) with NaBH4. The benzylic alcohol (XIII) was chlorinated to (XIV), which was converted to nitrile (XV) by chloride displacement with tetraethylammonium cyanide. Nitrile (XV) was subjected to Claisen condensation with ethyl formate, yielding (XVI), followed by sulfonylation with benzenesulfonyl chloride to afford (XVII), which was cyclized to the amino thiophene (XVIII) by treatment with ethyl thioglycolate (IV) as above. Condensation of (XVIII) with 2,5-dimethoxytetrahydrofuran (VI) produced the corresponding pyrrole derivative (XIX). After conversion of the ester group of (XIX) to amide (XX) upon heating with pyrrolidine (VIII), its cyclization with POCl3 furnished the thienopyrrolizinone (XXI). The O-benzyl protecting group of (XXI) was finally cleaved by treatment with HBr in HOAc.

1 Lisowski, V.; et al.; Design, synthesis and antiproliferative activity of tripentones: A new series of antitubulin agents. Bioorg Med Chem Lett 2001, 11, 16, 2205.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 18838 methyl 2-sulfanylacetate 2365-48-2 C3H6O2S 详情 详情
(VI) 12121 (Z)-4-(Dimethylamino)-3-imidazo[1,2-a]pyridin-6-yl-3-buten-2-one C13H15N3O 详情 详情
(VIII) 11376 Pyrrolidine 123-75-1 C4H9N 详情 详情
(XI) 18455 3-hydroxy-4-methoxybenzaldehyde; Isovanillin 621-59-0 C8H8O3 详情 详情
(XII) 10966 3-(Benzyloxy)-4-methoxybenzaldehyde; 3-Benzyloxy-4-methoxybenzaldehyde 6346-05-0 C15H14O3 详情 详情
(XIII) 23823 5-[4-hydroxy-2-(3-hydroxybutyl)-3,5,6-trimethylphenoxy]-2,2-dimethylpentanoic acid C20H32O5 详情 详情
(XIV) 52232 benzyl 5-(chloromethyl)-2-methoxyphenyl ether; 2-(benzyloxy)-4-(chloromethyl)-1-methoxybenzene C15H15ClO2 详情 详情
(XV) 52233 (3-Benzyloxy-4-methoxyphenyl)acetonitrile C16H15NO2 详情 详情
(XVI) 52234 sodium (Z)-2-[3-(benzyloxy)-4-methoxyphenyl]-2-cyano-1-ethenolate C17H14NNaO3 详情 详情
(XVII) 52235 (Z)-2-[3-(benzyloxy)-4-methoxyphenyl]-2-cyanoethenyl benzenesulfonate C23H19NO5S 详情 详情
(XVIII) 52236 methyl 3-amino-4-[3-(benzyloxy)-4-methoxyphenyl]-2-thiophenecarboxylate C20H19NO4S 详情 详情
(XIX) 52234 sodium (Z)-2-[3-(benzyloxy)-4-methoxyphenyl]-2-cyano-1-ethenolate C17H14NNaO3 详情 详情
(XX) 52238 [4-[3-(benzyloxy)-4-methoxyphenyl]-3-(1H-pyrrol-1-yl)-2-thienyl](1-pyrrolidinyl)methanone C27H26N2O3S 详情 详情
(XXI) 52239 3-[3-(benzyloxy)-4-methoxyphenyl]-8H-thieno[2,3-b]pyrrolizin-8-one C23H17NO3S 详情 详情
Extended Information