67498-53-7

Basic information

• Product Name: 7a-methyl-3-methylidenehexahydro-1-benzofuran-2(3H)-one
• Synonyms: 7a-Methyl-3-methylenehexahydro-1-benzofuran-2(3H)-one; 7a-Methyl-3-methylenehexahydrobenzofuran-2-one
• CAS NO: 67498-53-7
• Molecular Formula: C₁₀H₁₄O₂
• Molecular Weight: 166.217
• Mol File: 67498-53-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 284.5°C at 760 mmHg
• Flash Point: 114.6°C
• Density: 1.06g/cm³
• Vapor Pressure: 0.00296mmHg at 25°C
• Refractive Index: 1.496
• CAS DataBase Reference: 7a-methyl-3-methylidenehexahydro-1-benzofuran-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7a-methyl-3-methylidenehexahydro-1-benzofuran-2(3H)-one(67498-53-7)
• EPA Substance Registry System: 7a-methyl-3-methylidenehexahydro-1-benzofuran-2(3H)-one(67498-53-7)

Safety Data

• Hazardous Substances Data: 67498-53-7(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 74723-73-2 1-bromo-8-oxonon-2-yne 
• 50-00-0 formaldehyd 
• 128071-58-9 (E)-3-Chloro-2-(2-chloro-2-methyl-cyclohexyl)-acrylic acid 
• 128071-53-4 2-Chloro-3-(2-chloro-2-methyl-cyclohexyl)-cycloprop-2-enone 
• 113426-65-6 1-Chloro-1-methyl-2-(2,3,3-trichloro-cycloprop-1-enyl)-cyclohexane 
• 128071-71-6 (2-Chloro-2-methyl-cyclohexyl)-propynoyl chloride 
• 591-49-1 1-methylcyclohex-1-ene 
• 150546-39-7 3-Methyl-3-(1,2-propadienyloxy)-1-cyclohexene 
• 13373-66-5 1-Methyl-2-oxabicyclo<3.3.0^1,5>nonan-3-one 
• 118893-25-7 diethyl 2-(2-methyl-2-cyclohexen-1-yl)propane-1,3-dioate 
• 321166-01-2 (2-methyl-cyclohex-2-enyl)-acetic acid 
• 71593-68-5 ethyl (2-methyl-2-cyclohexenyl)acetate 
• 13295-90-4 2-methyl-2-cyclohexen-1-yl acetate 

Relevant articles and documents

Lactones, part 28: A new approach for the synthesis of α-methylene lactones from alkenes

A facile two-step procedure for synthesis of α-methylene lactones from alkenes and cycloalkenes is presented. Reactions carried out on some monoterpene alkenes afforded corresponding lactones in enantiomerically pure forms. Georg Thieme Verlag Stuttgart.

Synthetic studies towards (+)-Dihydroampullicin. Michael addition of N-Boc-2-(tert-butyldimethylsiloxy)-3-methyl-pyrrole to α-methylene lactones

The Michael addition of N-(tert-butoxycarbonyl)-2-(tert-butyldimethylsiloxy)-3-methyl-pyrrole (4) to several α-methylene lactones catalyzed by fluoride ions yielded the corresponding homologated products (26-30) with good yields. Application of this react

Tungsten-Mediated Syntheses of Fused α-Methylenebutyrolactones from Propargyl Bromides Containing Tethered Aldehydes and Ketones

The reaction of CpW(CO)3Na with a number of propargyl bromides with tethered aldehydes and ketones afforded η1-propargyl species that were subsequently transformed into tungsten-η3-2-(methoxycarbonyl)allyl compounds upon treatment with p-TSA/CH3OH; the overall yields exceeded 60%. Sequential treatment of these tungsten-η3-allyl complexes with NOBF4 and NaI in CH3CN led to intramolecular allyltungsten-carbonyl cyclization, yielding fused α-methylene butyrolactones of five-, six-, and seven-membered carbocyclic rings. All the reactions proceeded with high diastereoselectivities except for 9-methylene-7-oxabicyclo[4.3.0]nonan-8-one (22) and 10-methylene-8-oxabicyclo[5.3.0]decan-9-one (23). Modification of the metal center with a chloride ligand led to significant improvement of the trans-stereoselection of 22; the chloride modification did not significantly enhance stereoselection of 23. The stereochemical course of the reaction products is rationalized on the basis of a bicyclic transition-state mechanism.