2,3,5,6-tetramethylidene-7-oxabicyclo[2.2.1]heptane

Base Information

• Chemical Name: 2,3,5,6-tetramethylidene-7-oxabicyclo[2.2.1]heptane
• CAS No.: 53011-99-7
• Molecular Formula: C10H10O
• Molecular Weight: 146.189
• Mol file: 53011-99-7.mol

Synonyms:7-Oxabicyclo[2.2.1]heptane,2,3,5,6-tetramethylidene;2,3,5,6-tetrakis(methylene)-7-oxabicyclo<2.2.1>AC1L3M96;2,3,5,6-tetrakis(methylene)-7-oxanorbornane;2,3,5,6-tetramethylidene-7-oxanorbornane;2,3,5,6-tetramethylidene-7-oxatrinorbornane;2,3,5,6-tetramethylidene-7-oxabicyclo{2.2.1}heptane;2,3,5,6-tetramethylene-7-oxabicyclo<2,3,5,6-Tetramethylidene-7-oxabicyclo<

Chemical Property of 2,3,5,6-tetramethylidene-7-oxabicyclo[2.2.1]heptane

Chemical Property:

• Vapor Pressure: 0.235mmHg at 25°C
• Melting Point: 35-36 °C
• Boiling Point: 213.8°C at 760 mmHg
• Flash Point: 78.1°C
• PSA: 9.23000
• Density: 1.01g/cm³
• LogP: 1.99220

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,3,5,6-tetramethylidene-7-oxabicyclo[2.2.1]heptane

There total 2 articles about 2,3,5,6-tetramethylidene-7-oxabicyclo[2.2.1]heptane 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:

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride (6118-51-0) → 2,3,5,6-tetramethylidene-7-oxabicyclo<2.2.1>heptane (53011-99-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 71 percent / CuCl₂, NaOAc, 10percent Pd/C / 8 h / 2280 Torr / Ambient temperature

2: 46 percent / LiAlH₄ / tetrahydrofuran / 4 h / Heating

3: 83 percent / SOCl₂, pyridine / 2 h / 60 - 70 °C

4: 89 percent / t-BuOK / tetrahydrofuran / 14 h / 0 °C

With pyridine; palladium on activated charcoal; lithium aluminium tetrahydride; thionyl chloride; potassium tert-butylate; sodium acetate; copper dichloride; In tetrahydrofuran;

DOI:10.1021/ja00042a009

Reference yield:

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride (6118-51-0) → 2,3,5,6-tetrakis(methylene)-7-oxabicyclo<2.2.1>heptane (53011-99-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / CuCl₂ / 10percent Pd/C / 4 h / 3040 Torr / Ambient temperature

2: 83 percent / LiAlH₄ / tetrahydrofuran / 1) 0 deg C, 1.5 h, 2) reflux, 4 h

3: 85 percent / SOCl₂, pyridine / 2 h / 60 - 70 °C

4: 98 percent / t-BuOK / tetrahydrofuran / 12 h / Ambient temperature

With pyridine; lithium aluminium tetrahydride; thionyl chloride; potassium tert-butylate; copper dichloride; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1002/hlca.19800630506

Reference yield: 55.0%

2,3,5,6-tetrakis(methylene)-7-oxabicyclo<2.2.1>heptane (53011-99-7) → 3,5,6-Trimethylidene-7-oxabicyclo<2.2.1>heptane-2-one (127750-96-3)

Guidance literature:

With oxygen; ozone; In toluene; at -90 ℃;

DOI:10.1002/hlca.19900730102

upstream raw materials:

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride

Downstream raw materials:

3,5,6-Trimethylidene-7-oxabicyclo<2.2.1>heptane-2-one

3,5-Dimethylidene-7-oxabicyclo<2.2.1>heptane-2,6-dione

3,6-Dimethylidene-7-oxabicyclo<2.2.1>heptane-2,5-dione

2,5-Bis<<(Z)-(2-nitrophenyl)sulfenyl>methylene>-3,6-dimethylene-7-oxabicyclo<2.2.1>heptane

Refernces

• 1、 Mahaim, Cyril,Carrupt, Pierre-Alain,Hagenbuch, Jean-Pierre,Florey, Andre,Vogel, Pierre. "An Efficient Synthesis of 2,3,5,6-Tetramethylidene-7-oxanorbornane". . p. 1149 - 1157. Retrieved 2007/10/02.