1-(Methoxymethyl)-6-oxabicyclo[3.1.0]hex-3-en-2-one

Base Information

• Chemical Name: 1-(Methoxymethyl)-6-oxabicyclo[3.1.0]hex-3-en-2-one
• CAS No.: 112698-65-4
• Molecular Formula: C₇H₈O₃
• Molecular Weight: 140.139
• DSSTox Substance ID: DTXSID00561707
• Mol file: 112698-65-4.mol

Synonyms:112698-65-4;1-(Methoxymethyl)-6-oxabicyclo[3.1.0]hex-3-en-2-one;DTXSID00561707

Chemical Property of 1-(Methoxymethyl)-6-oxabicyclo[3.1.0]hex-3-en-2-one

Chemical Property:

• XLogP3: -0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 140.047344113
• Heavy Atom Count: 10
• Complexity: 209

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COCC12C(O1)C=CC2=O

Technology Process of 1-(Methoxymethyl)-6-oxabicyclo[3.1.0]hex-3-en-2-one

There total 10 articles about 1-(Methoxymethyl)-6-oxabicyclo[3.1.0]hex-3-en-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: 57.0%

(-)-exo-4,5-Epoxy-endo-4-methoxymethyl-exo-10-oxatricyclo<5.2.1.02,6>deca-8-en-3-one (112698-62-1,130790-88-4) → (+)-4,5-Epoxy-5-methoxymethyl-2-cyclopentenone (112698-65-4,129076-44-4,130195-91-4)

Guidance literature:

at 360 ℃; flash vacuum pyrolysis;

DOI:10.1016/S0040-4020(01)86766-1

Reference yield:

4-methoxymethyl-exo-10-oxatricyclo<5.2.1.02,6>deca-4,8-dien-3-one (112723-14-5,130195-88-9,130195-89-0,130195-90-3) → 4,5-epoxy-5-methoxymethyl-2-cyclopentenone (112698-65-4,129076-44-4,130195-91-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / 33percent hydrogen peroxide, 0.2 N sodium hydroxide / methanol; CH₂Cl₂; H₂O / 2 h

2: 1.5 h / 0.05 - 0.06 Torr / flash vacuum thermolysis; T₁ 90 deg C / T₂ 360 deg C

With sodium hydroxide; dihydrogen peroxide; In methanol; dichloromethane; water;

DOI:10.1016/S0040-4020(01)89180-8

Reference yield:

5-ethoxy-4-(p-tolylsulphonyl)methyl-exo-10-oxatricyclo<5.2.1.02,6>deca-4,8-dien-3-one (112698-71-2) → 4,5-epoxy-5-methoxymethyl-2-cyclopentenone (112698-65-4,129076-44-4,130195-91-4)

Guidance literature:

Multi-step reaction with 4 steps

1: methanol / 0.17 h / Heating

2: DIBAL / hexane

3: H₂O₂, OH^(1-)

4: 330 °C / flash vacuum thermolysis

With hydroxide; dihydrogen peroxide; diisobutylaluminium hydride; In methanol; hexane;

DOI:10.1016/S0040-4039(00)95362-0

upstream raw materials:

exo-4,5-epoxy-endo-4-methoxymethyl-exo-oxatricyclo<5.2.1.0^2,6>deca-8-en-3-one

4-methoxymethyl-exo-10-oxatricyclo<5.2.1.0^2,6>deca-4,8-dien-3-one

5-ethoxy-4-(p-tolylsulphonyl)methyl-exo-10-oxatricyclo<5.2.1.0^2,6>deca-4,8-dien-3-one

5-hydroxy-exo-10-oxatricyclo<5.2.1.0^2,6>deca-4,8-dien-3-one

Downstream raw materials:

(4S^*,5R^*)-5-(3,5-Dinitrophenylcarbonyloxy)-4-methoxy-5-methoxymethyl-2-cyclopentenone