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【结 构 式】

【分子编号】40150

【品名】(1S,4R,5R,9R,10R,12R,13R,17R)-19-isopropyl-5,9-dimethyl-14,16-dioxo-15-oxapentacyclo[10.5.2.0(1,10).0(4,9).0(13,17)]nonadec-18-ene-5-carboxylic acid

【CA登记号】

【 分 子 式 】C24H32O5

【 分 子 量 】400.51508

【元素组成】C 71.97% H 8.05% O 19.97%

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:(I)

The reaction of maleopimaric acid (I) with aqueous ammonia and heating at 170 C gives maleopimarimide (II), which by reaction with oxalyl chloride in benzene is converted into the corresponding acyl chloride (III). The reaction of (III) with morpholine (A) in benzene yields maleopimarimidyl morpholide (IV), which is finally condensed with ethanolamine (B) in refluxing methanol.

1 Danswan, G.W.; Ramm, P.J.; Matharu, S.; Taylor, J.B.; hepatoprotective agents. II. Maleopimaridyl morpholides. Arzneim-Forsch Drug Res 1976, 26, 12, 2190-92.
2 Thorpe, P.; Castaner, J.; RU 18492. Drugs Fut 1977, 2, 9, 623.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(B) 10259 Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol;2-Aminoethyl alcohol 141-43-5 C2H7NO 详情 详情
(A) 10388 Morpholine 110-91-8 C4H9NO 详情 详情
(I) 40150 (1S,4R,5R,9R,10R,12R,13R,17R)-19-isopropyl-5,9-dimethyl-14,16-dioxo-15-oxapentacyclo[10.5.2.0(1,10).0(4,9).0(13,17)]nonadec-18-ene-5-carboxylic acid C24H32O5 详情 详情
(II) 40151 (1S,4R,5R,9R,10R,12R,13R,17R)-19-isopropyl-5,9-dimethyl-14,16-dioxo-15-azapentacyclo[10.5.2.0(1,10).0(4,9).0(13,17)]nonadec-18-ene-5-carboxylic acid C24H33NO4 详情 详情
(III) 40152 (1S,4R,5R,9R,10R,12R,13R,17R)-19-isopropyl-5,9-dimethyl-14,16-dioxo-15-azapentacyclo[10.5.2.0(1,10).0(4,9).0(13,17)]nonadec-18-ene-5-carbonyl chloride C24H32ClNO3 详情 详情
(IV) 40153 (1S,4R,5R,9R,10R,12R,13R,17R)-19-isopropyl-5,9-dimethyl-5-(4-morpholinylcarbonyl)-15-azapentacyclo[10.5.2.0(1,10).0(4,9).0(13,17)]nonadec-18-ene-14,16-dione C28H40N2O4 详情 详情

合成路线2

该中间体在本合成路线中的序号:(I)

The reaction of maleopimaric acid (I) with SOCl2 in benzene produces the corresponding acyl chloride (V), which is then condensed with morpholine (A) by means of Et3N in benzene yielding maleopimaryl morpholide (VI). Finally, (VI) is condensed with ethanolamine (B) in refluxing ethanol.

1 Taylor, J.B.; et al. (Aventis Pharma SA); Novel derivatives of maleopimaric acid. DE 2351343; FR 2202691; GB 1417996; JP 49093356; US 3998823 .
2 Thorpe, P.; Castaner, J.; RU 18492. Drugs Fut 1977, 2, 9, 623.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(B) 10259 Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol;2-Aminoethyl alcohol 141-43-5 C2H7NO 详情 详情
(A) 10388 Morpholine 110-91-8 C4H9NO 详情 详情
(I) 40150 (1S,4R,5R,9R,10R,12R,13R,17R)-19-isopropyl-5,9-dimethyl-14,16-dioxo-15-oxapentacyclo[10.5.2.0(1,10).0(4,9).0(13,17)]nonadec-18-ene-5-carboxylic acid C24H32O5 详情 详情
(V) 40155 (1S,4R,5R,9R,10R,12R,13R,17R)-19-isopropyl-5,9-dimethyl-14,16-dioxo-15-oxapentacyclo[10.5.2.0(1,10).0(4,9).0(13,17)]nonadec-18-ene-5-carbonyl chloride C24H31ClO4 详情 详情
(VI) 40154 (1S,4R,5R,9R,10R,12R,13R,17R)-19-isopropyl-5,9-dimethyl-5-(4-morpholinylcarbonyl)-15-oxapentacyclo[10.5.2.0(1,10).0(4,9).0(13,17)]nonadec-18-ene-14,16-dione C28H39NO5 详情 详情
Extended Information