36679-81-9

Basic information

• Product Name: 4-(hydroxymethyl)dihydrofuran-2(3H)-one
• Synonyms: 4-(hydroxymethyl)dihydrofuran-2(3H)-one;Dihydro-4-(Hydroxymethyl)Furan-2(3H)-One;4-Hydroxymethyl-dihydro-furan-2-one
• CAS NO: 36679-81-9
• Molecular Formula: C₅H₈O₃
• Molecular Weight: 116.11522
• Mol File: 36679-81-9.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(hydroxymethyl)dihydrofuran-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(hydroxymethyl)dihydrofuran-2(3H)-one(36679-81-9)
• EPA Substance Registry System: 4-(hydroxymethyl)dihydrofuran-2(3H)-one(36679-81-9)

Safety Data

• Hazardous Substances Data: 36679-81-9(Hazardous Substances Data)

Upstream product

• 922500-91-2 ethyl 2-(oxetan-3-ylidene)acetate 
• 81189-55-1 acetic acid 5-oxo-2,5-dihydrofuran-3-ylmethyl ester 
• 75887-43-3 4-bromo-3-(bromomethyl)but-2-enoic acid 
• 61934-55-2 3-bromomethyl-2-butenolide 
• 541-47-9 3-Methylbutenoic acid 
• 5204-92-2 ethyl 5-oxotetrahydro-3-furancarboxylate 
• 42927-61-7 methyl 5-methoxy-3-tetrahydrofuran-3-carboxylate 
• 183616-18-4 3-(hydroxymethyl)-cyclobutan-1-one 
• 5472-38-8 diethyl 2-formylbutanedioate 
• 143724-42-9 (rel)-(1S/1R,3S)-(tetrahydro-1-methoxyfuran-3-yl)methanol 
• 498-89-5 paraconic acid 
• 96-48-0 4-butanolide 
• 67-56-1 methanol 
• 80904-75-2 4-hydroxymethyl-5H-furan-2-one 

Downstream Products

• 51311-41-2 3-hydroxymethyl-2-(6-methylheptanoyl)-4-butanolide 
• 1620754-39-3 (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (5-oxotetrahydrofuran-3-yl)methyl carbonate 
• 193070-22-3 (±)-4-[(benzyloxy)methyl]-dihydrofuran-2(3H)-one 
• 1614252-03-7 10-(4-chlorothiazol-2-yl)-5-(3-fluorophenyl)-8-(hydroxymethyl)-1,3-dimethyl-7,8-dihydropyrimido[4,5-a]indolizine-2,4(1H,3H)-dione 
• 1614252-02-6 6-(2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(4-chlorothiazol-2-yl)-4-oxobutyl)-5-(3-fluorophenyl)-1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione 
• 1614252-01-5 4-((tert-butyldimethylsilyl)oxy)-3-((5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)methyl)-N-methoxy-N-methylbutanamide 
• 1614252-00-4 4-((tert-butyldimethylsilyl)oxy)-3-((5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)methyl)butanoic acid 
• 1614251-99-8 sodium 4-(5-(3-fluorophenyl)-1,3-dimethyl-2,4-dioxo-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)-3-(hydroxymethyl)butanoate 
• 1614251-98-7 5-(3-fluorophenyl)-1,3-dimethyl-6-((5-oxotetrahydrofuran-3-yl)methyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione 
• 1309477-61-9 (E)-1-(4-(4-methoxybenzyloxymethyl)-2-oxodihydrofuran-3(2H)-ylidene)ethyl dimethyl phosphate 
• 1309477-60-8 3-acetyl-4-((4-methoxybenzyloxy)methyl)dihydrofuran-2(3H)-one 
• 791856-62-7 5-(4-bromophenyl)-3-(2-tert-butyldimethylsilyloxymethyl-3-(2-phenylimidazol-1-yl)propyl)-1,2,4-triazine 
• 791856-63-8 5-(4-methoxyphenyl)-3-(2-tert-butyldimethylsilyloxymethyl-3-(2-phenylimidazol-1-yl)propyl)-1,2,4-triazine 
• 791856-61-6 5-phenyl-3-(2-tert-butyldimethylsilyloxymethyl-3-(2-phenylimidazol-1-yl)propyl)-1,2,4-triazine 

Relevant articles and documents

Synthesis method of 4-hydroxymethyl-dihydro-furan-2(3H)-ketone

The invention belongs to the field of organic synthesis and drug synthesis, and particularly relates to a synthesis method of 4-hydroxymethyl-dihydro-furan-2(3H)-ketone. The synthesis method is carried out by a first step of mixing and stirring 3-oxetanone and ethoxyformyl methylidene triphenyl phosphorane solvent and obtaining an intermediate product 2-(oxetane-3-radical) ethyl acetate; a second step of hydrolyzing the intermediate product 2-(oxetane-3-radical) ethyl acetate through palladium carbon hydrogenation reduction under the alkali condition; meanwhile, completing rearrangement of reduction and oxygen heterocycles; obtaining 4-hydroxymethyl-dihydro-furan-2(3H)-ketone. The reaction condition of the synthesis method involved in the invention is easy to control, raw materials are low-price and easy to obtain; the operation and post treatment processes are simple; besides, the method is possessed of the industrial production value.

Application of the palladium-catalysed norbornene-assisted catellani reaction towards the total synthesis of (+)-linoxepin and isolinoxepin

Our ongoing effort towards the development of highly selective transition-metal-catalysed C-H activation processes has led to the expansion of the Catellani reaction. In a Pd0/PdII/Pd IV-catalysed domino reaction, an aryl iodide, alkyl iodide and tert-butyl acrylate were combined to synthesize the carbon framework of the novel lignan (+)-linoxepin. The enantioselective synthesis highlights the work accomplished in our group and provides an excellent procedure for the reliable and scalable synthesis of architecturally complex scaffolds. This report outlines the synthetic approaches towards this interesting class of biologically active molecules. After the key Catellani/Heck reaction, our synthesis features a Leimeux-Johnson oxidation and a titanium tetrachloride mediated aldol condensation. Finally, a tuneable Mizoroki-Heck reaction was performed to furnish not only the natural product (+)-linoxepin but also its isoform, which we have named isolinoxepin. The enantioselective total synthesis of the natural product (+)-linoxepin has been accomplished in eight steps starting from commercial materials. The key Pd-catalysed Catellani step served to combine aryl iodide, alkyl iodide and tert-butyl acrylate in a domino sequence. By tuning the final Heck reaction, both the natural product and its structural isomer were synthesized. Copyright

Total synthesis of (+)-linoxepin by utilizing the catellani reaction

Molecular intelligence: The structurally novel lignan (+)-linoxepin is synthesized in an eight-step sequence. The enantioselective synthesis features the palladium-catalyzed Catellani reaction as the key step. In this highly convergent multicomponent reaction, two new carbon-carbon bonds are formed, one of which results from a C-H bond functionalization. Copyright