1-Ethenyl-2-oxabicyclo[2.2.2]octane-4-carboxylic acid

Base Information

• Chemical Name: 1-Ethenyl-2-oxabicyclo[2.2.2]octane-4-carboxylic acid
• CAS No.: 340023-04-3
• Molecular Formula: C₁₀H₁₄O₃
• Molecular Weight: 182.219
• DSSTox Substance ID: DTXSID801214545
• Mol file: 340023-04-3.mol

Synonyms:340023-04-3;1-ethenyl-2-oxabicyclo[2.2.2]octane-4-carboxylic acid;1-Vinyl-2-oxabicyclo[2.2.2]octane-4-carboxylic acid;MFCD20658989;SCHEMBL1566353;DTXSID801214545;AKOS025289980;AB91805;AS-51507;SY233987;CS-0058907;P12820;1-Vinyl-2-oxabicyclo[2.2.2]octane-4-carboxylicacid

Chemical Property of 1-Ethenyl-2-oxabicyclo[2.2.2]octane-4-carboxylic acid

Chemical Property:

• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 182.094294304
• Heavy Atom Count: 13
• Complexity: 249

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=CC12CCC(CC1)(CO2)C(=O)O

Technology Process of 1-Ethenyl-2-oxabicyclo[2.2.2]octane-4-carboxylic acid

There total 11 articles about 1-Ethenyl-2-oxabicyclo[2.2.2]octane-4-carboxylic acid 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: 74.0%

(1-vinyl-2-oxabicyclo[2.2.2]octan-4-yl)methanol (340023-03-2) → 1-vinyl-2-oxabicyclo[2.2.2]octane-4-carboxylic acid (340023-04-3)

Guidance literature:

With pyridinium dichromate; In N,N-dimethyl-formamide; at 25 - 40 ℃; for 3.5h;

DOI:10.1021/ml500069w

Reference yield:

triethyl 4-oxocyclohexane-1,1,3-tricarboxylate (57899-62-4) → 1-vinyl-2-oxabicyclo[2.2.2]octane-4-carboxylic acid (340023-04-3)

Guidance literature:

Multi-step reaction with 10 steps

1: sodium chloride / water; dimethyl sulfoxide / 1.7 h / 160 °C

2: toluene-4-sulfonic acid / toluene / 4 h / Reflux

3: lithium aluminium tetrahydride / diethyl ether / 3 h / -20 - 0 °C

4: pyridine / 20 °C / Cooling with ice

5: hydrogenchloride / tetrahydrofuran / 5 h / Reflux

6: tetrahydrofuran / 5.25 h / -78 °C

7: sodium hydride / mineral oil; 1,2-dimethoxyethane / 3 h / Cooling with ice; Reflux

8: N,N-dimethyl-formamide / 100 °C

9: potassium carbonate; water / methanol / 2 h / 20 °C / Cooling with ice

10: dipyridinium dichromate / N,N-dimethyl-formamide / 3.5 h / 40 °C / Cooling with ice

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; dipyridinium dichromate; water; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; sodium chloride; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; mineral oil;

Reference yield:

4-oxo-cyclohexane-1,1-dicarboxylic acid diethyl ester (55704-60-4) → 1-vinyl-2-oxabicyclo[2.2.2]octane-4-carboxylic acid (340023-04-3)

Guidance literature:

Multi-step reaction with 9 steps

1: toluene-4-sulfonic acid / toluene / 4 h / Reflux

2: lithium aluminium tetrahydride / diethyl ether / 3 h / -20 - 0 °C

3: pyridine / 20 °C / Cooling with ice

4: hydrogenchloride / tetrahydrofuran / 5 h / Reflux

5: tetrahydrofuran / 5.25 h / -78 °C

6: sodium hydride / mineral oil; 1,2-dimethoxyethane / 3 h / Cooling with ice; Reflux

7: N,N-dimethyl-formamide / 100 °C

8: potassium carbonate; water / methanol / 2 h / 20 °C / Cooling with ice

9: dipyridinium dichromate / N,N-dimethyl-formamide / 3.5 h / 40 °C / Cooling with ice

With pyridine; hydrogenchloride; lithium aluminium tetrahydride; dipyridinium dichromate; water; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; N,N-dimethyl-formamide; toluene; mineral oil;

upstream raw materials:

(1-vinyl-2-oxabicyclo[2.2.2]octan-4-yl)methanol

triethyl 4-oxocyclohexane-1,1,3-tricarboxylate

4-oxo-cyclohexane-1,1-dicarboxylic acid diethyl ester

8,8-diethyl 1,4-dioxaspiro[4.5]decane-8,8-dicarboxylate

Downstream raw materials:

tert-butyl N-(4-formyl-3-oxabicyclo[2.2.2]octan-1-yl)carbamate

tert-butyl (1-ethenyl-2-oxabicyclo[2.2.2]oct-4-yl)carbamate

t-butyl 1-(2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-1-hydroxyethyl)-2-oxabicyclo[2.2.2]octan-4-ylcarbamate

t-butyl 1-(2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)-1-hydroxyethyl)-2-oxabicyclo[2.2.2]octan-4-ylcarbamate