4,4-Dimethyl-5-methylideneoxolan-2-one

Base Information

• Chemical Name: 4,4-Dimethyl-5-methylideneoxolan-2-one
• CAS No.: 65371-43-9
• Molecular Formula: C₇H₁₀O₂
• Molecular Weight: 126.155
• DSSTox Substance ID: DTXSID40369168
• Nikkaji Number: J392.628A
• Wikidata: Q82156202
• Mol file: 65371-43-9.mol

Synonyms:65371-43-9;4,4-DIMETHYL-5-METHYLENE-GAMMA-BUTYROLACTONE;4,4-dimethyl-5-methylideneoxolan-2-one;SCHEMBL8394043;DTXSID40369168;AKOS000279304;FT-0641014;4,4-Dimethyl-5-methylenetetrahydrofuran-2-one;4,4-dimethyl-5-methylenedihydro-2(3H)-furanone;4,4-dimethyl-5-methylenedihydrofuran-2(3H)-one;EN300-23904331

Chemical Property of 4,4-Dimethyl-5-methylideneoxolan-2-one

Chemical Property:

• Refractive Index: 1.449-1.451
• Boiling Point: 52-55 °C(Press: 5-6 Torr)
• PSA: 26.30000
• Density: 1.01±0.1 g/cm3(Predicted)
• LogP: 1.47320
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 126.068079557
• Heavy Atom Count: 9
• Complexity: 168

Purity/Quality:

97% ^*data from raw suppliers

4,4-DIMETHYL-5-METHYLENE-G-BUTYROLACTONE 95.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC(=O)OC1=C)C

Technology Process of 4,4-Dimethyl-5-methylideneoxolan-2-one

There total 11 articles about 4,4-Dimethyl-5-methylideneoxolan-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

3,3-dimethyl-4-pentynoic acid (67099-40-5) → 3,3-Dimethyl-4-penten-4-olide (65371-43-9)

Guidance literature:

With palladium dichloride;

DOI:10.1021/ja983698d

Reference yield: 81.0%

5-iodomethyl-4,4-dimethyltetrahydrofuran-2-one (65371-41-7) → 3,3-Dimethyl-4-penten-4-olide (65371-43-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; at 70 - 80 ℃; for 3h;

Reference yield: 74.0%

4,5-dihydro-4,4-dimethyl-5-phenylsulfoxymethyl (3H)-furan-2-(one) (121402-78-6) → 3,3-Dimethyl-4-penten-4-olide (65371-43-9)

Guidance literature:

With sodium carbonate; at 160 - 180 ℃; under 10 Torr;

upstream raw materials:

5-iodomethyl-4,4-dimethyltetrahydrofuran-2-one

3,3-dimethylpent-4-enoic acid

4,5-dihydro-4,4-dimethyl-5-phenylsulfoxymethyl (3H)-furan-2-(one)

3-chloro-3-methylbut-1-yne

Refernces

• 1、 Mori, Kenji. "Pheromone synthesis. Part 264: Synthesis of the core 3-oxabicyclo[3.3.0]octane structures of gomadalactones A, B and C, the components of the contact sex pheromone of the white-spotted longicorn beetle, Anoplophora malasiaca". . p. 3387 - 3398. Retrieved 2019/05/15.
• 2、 Maeno, Zen,Mitsudome, Takato,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi. "Intramolecular cyclization of γ-acetylenic acids using dendrimer-encapsulated Pd2+ catalysts". . p. 947 - 954. Retrieved 2013/08/15.