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&-Propiolactone
（CAS编码：57-57-8　产品编码：H0168）
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纯度/分析方法
>95.0%(GC)(T)
分子式(M.F.) / 分子量(M.W.)
C3H4O2=72.06
相关CAS编码
监管条件代码(*)
国内危险化学品序号
Purity(GC)
min. 95.0 %
Purity(Iodometric Titration)
min. 95.0 %
Specific gravity (20/20)
1.1460 to 1.1520
Refractive index n20/D
1.4110 to 1.4150
闪点(flp)
74&C(lit.)
沸点(bp)
165&C(lit.)
17(3/4)41
PubChem SID
Merck Index(14)
图形或危害标志
危险有害信息
:吞咽会中毒
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PubMed Literature
& 梯希爱(上海)化成工业发展有限公司 &&&&沪ICP备号& 57-57-8,C3H4O2,72.0641,2-oxetanone
57-57-8,C3H4O2,72.0641,2-oxetanone
摘 要：57-57-8,C3H4O2,72.0641,2-oxetanone
【化学名】2-oxetanone
【CAS登记号】57-57-8
【结构式】
【分子式】C3H4O2
【分子量】72.0641
【来源】ABCR GmbH & Co.; Acros O A George Uhe Company, Inc.; ICN Biomedical Research P Oakwood Products, Inc.; Sigma Chemical C Spectrum Quality Products, Inc.; TCI; Toronto Research Chemicals, Inc.
【合成情况】　
〖目标产物〗Beraprost sodium, RU-55100, ML-1229(free acid), ML-1129, TRK-100, Beraprost, Dorner, Procylin
〖合成路线〗
〖合成方法〗The reaction of 7-bromo-3a,8b-cis-3a,8b dihydro-3H-5-cyclopenta[b]benzofurancarboxylic acid (I) with trioxane and H2SO4, followed by methylation with diazomethane and debromination with H2 over Pd/C, gives the hydroxymethyl compound (II), which is protected with 1,1-diethoxyethane and p-toluenesulfonic acid to give the protected ester (III). Reduction of the ester (III) with LiAlH4 in THF affords the corresponding hydroxymethyl compound (IV), which by reaction with SOCl2 in DMF is converted to the chlorometnyl derivative (VI). The condensation of (V) with beta-propiolactone (VI) by means of Mg in TFH gives the phenylbutyric acid (VII), which by methylation with diazomethane and deprotection with HCl in metnanol yields the dihydroxyester (VIII). Selective acetylation of (VIII) by reaction with trimethyl-tert-butylchlorosilane, then with acetic anhydride and final desilylation with acetic acid affords methyl 4-(2alpha-acetoxy-1-hydroxymethyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuranyl)butyrate (IX), which is oxidized with DMSO. dicyclohexylcarbodiimide (DCC) and trifluoroacetic acid to the corresponding aldehyde (X). The Wittig condensation of (X) with dimethyl 3-methyl-2-oxohept-5-yn-1-yl phosphonate (XI) by means of NaH in DMF affords 11,15-dideoxy-11-acetoxy-16-methyl-15-oxo-18,19-tetradehydro-5,6,7-trinor-4,8-inter-m-phenylene-prostaglandin I2 methyl ester (XII), vvhich is reduced with cerium chloride and NaBH4 in methanol to the corresponding 15-hydroxy compound (XIII). Finally, this compound is deacetylated and saponified as usual.
〖参考〗Castaer, J.; Prous, J.; TRK-100. Drugs Fut , 956
〖目标产物〗Beraprost sodium, RU-55100, ML-1229(free acid), ML-1129, TRK-100, Beraprost, Dorner, Procylin
〖合成路线〗
〖合成方法〗The reaction of 7-bromo-3a,8b-cis-3a,8b dihydro-3H-5-cyclopenta[b]benzofurancarboxylic acid (I) with trioxane and H2SO4, followed by methylation with diazomethane and debromination with H2 over Pd/C, gives the hydroxymethyl compound (II), which is protected with 1,1-diethoxyethane and p-toluenesulfonic acid to give the protected ester (III). Reduction of the ester (III) with LiAlH4 in THF affords the corresponding hydroxymethyl compound (IV), which by reaction with SOCl2 in DMF is converted to the chlorometnyl derivative (VI). The condensation of (V) with beta-propiolactone (VI) by means of Mg in TFH gives the phenylbutyric acid (VII), which by methylation with diazomethane and deprotection with HCl in metnanol yields the dihydroxyester (VIII). Selective acetylation of (VIII) by reaction with trimethyl-tert-butylchlorosilane, then with acetic anhydride and final desilylation with acetic acid affords methyl 4-(2alpha-acetoxy-1-hydroxymethyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuranyl)butyrate (IX), which is oxidized with DMSO. dicyclohexylcarbodiimide (DCC) and trifluoroacetic acid to the corresponding aldehyde (X). The Wittig condensation of (X) with dimethyl 3-methyl-2-oxohept-5-yn-1-yl phosphonate (XI) by means of NaH in DMF affords 11,15-dideoxy-11-acetoxy-16-methyl-15-oxo-18,19-tetradehydro-5,6,7-trinor-4,8-inter-m-phenylene-prostaglandin I2 methyl ester (XII), vvhich is reduced with cerium chloride and NaBH4 in methanol to the corresponding 15-hydroxy compound (XIII). Finally, this compound is deacetylated and saponified as usual.
〖参考〗Ohno, K.; Nagase, H.; Matsumoto, K.; Nishio, S. (Toray Industries, Inc.); 5,6,7-Trinor-4,8-inter-m-phenylene protaglandin I2 derivatives useful in anti-ulcer, hypotensive and platelet aggregation inhibiting compositions. EP 0084856; JP ; US 447480i>
〖目标产物〗Beraprost sodium, RU-55100, ML-1229(free acid), ML-1129, TRK-100, Beraprost, Dorner, Procylin
〖合成路线〗
〖合成方法〗The reaction of 7-bromo-3a,8b-cis-3a,8b dihydro-3H-5-cyclopenta[b]benzofurancarboxylic acid (I) with trioxane and H2SO4, followed by methylation with diazomethane and debromination with H2 over Pd/C, gives the hydroxymethyl compound (II), which is protected with 1,1-diethoxyethane and p-toluenesulfonic acid to give the protected ester (III). Reduction of the ester (III) with LiAlH4 in THF affords the corresponding hydroxymethyl compound (IV), which by reaction with SOCl2 in DMF is converted to the chlorometnyl derivative (VI). The condensation of (V) with beta-propiolactone (VI) by means of Mg in TFH gives the phenylbutyric acid (VII), which by methylation with diazomethane and deprotection with HCl in metnanol yields the dihydroxyester (VIII). Selective acetylation of (VIII) by reaction with trimethyl-tert-butylchlorosilane, then with acetic anhydride and final desilylation with acetic acid affords methyl 4-(2alpha-acetoxy-1-hydroxymethyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuranyl)butyrate (IX), which is oxidized with DMSO. dicyclohexylcarbodiimide (DCC) and trifluoroacetic acid to the corresponding aldehyde (X). The Wittig condensation of (X) with dimethyl 3-methyl-2-oxohept-5-yn-1-yl phosphonate (XI) by means of NaH in DMF affords 11,15-dideoxy-11-acetoxy-16-methyl-15-oxo-18,19-tetradehydro-5,6,7-trinor-4,8-inter-m-phenylene-prostaglandin I2 methyl ester (XII), vvhich is reduced with cerium chloride and NaBH4 in methanol to the corresponding 15-hydroxy compound (XIII). Finally, this compound is deacetylated and saponified as usual.
〖参考〗Matsumoto, K.; Nagase, H.; Ohno, K. (Toray Industries, Inc.); Preparation of 5,6,7-trinor-4,8-inter-m-phenylene pgi2derivative. JP
〖目标产物〗SB-425076
〖合成路线〗
〖合成方法〗Condensation of 4-ethylaniline (I) with propiolactone (II) produces the beta-aminoacid (III). Intramolecular Friedel-Crafts cyclization of (III) by means of polyphosphoric acid leads to the quinolinone (IV). Then, electrophilic iodination of (IV) by using iodine monochloride provides the intermediate (V)
〖参考〗Jarvest, R.L.; Berge, J.M.; Berry, V.; et al.; Nanomolar inhibitors of Staphylococcus aureus methionyl tRNA synthetase with potent antibacterial activity against Gram-positive pathogens. J Med Chem , 1959
〖目标产物〗SB-425076
〖合成路线〗
〖合成方法〗Condensation of 4-ethylaniline (I) with propiolactone (II) produces the beta-aminoacid (III). Intramolecular Friedel-Crafts cyclization of (III) by means of polyphosphoric acid leads to the quinolinone (IV). Then, electrophilic iodination of (IV) by using iodine monochloride provides the intermediate (V)
〖参考〗Berge, J.M.; Forrest, A.K.; Elder, J.S.; Jarvest, R.L. (GlaxoSmithKline plc); Quinolones as t-RNA synthetase inhibitors and antibacterial agents. WO 0021949
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