7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Base Information

• Chemical Name: 7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
• CAS No.: 24363-23-3
• Molecular Formula: C7H8O3
• Molecular Weight: 140.139
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID60390171
• Nikkaji Number: J1.577.948I
• Mol file: 24363-23-3.mol

Synonyms:24363-23-3;7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid;7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid;C7H8O3;HMS1695J14;SCHEMBL950906;DTXSID60390171;HLZLZWREBWOZCZ-UHFFFAOYSA-N;MFCD06589820;7-oxanorborn-2-ene-5-carboxylic acid;AKOS015840950;BB 0220348;CS-0270782;FT-0689561;EN300-217224;7-Oxabicyclo[2.2.1]hept-5-en-2-carboxylic acid;7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylicacid;7-Oxabicyclo[2.2.1]hepta-5-ene-2-carboxylic acid

Chemical Property of 7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Chemical Property:

• Boiling Point: 299℃
• PKA: 4.25±0.20(Predicted)
• Flash Point: 132℃
• PSA: 46.53000
• Density: 1.376
• LogP: 0.41450
• Solubility.: Chloroform
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 140.047344113
• Heavy Atom Count: 10
• Complexity: 197

Purity/Quality:

98%Min ^*data from raw suppliers

7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C=CC(C1C(=O)O)O2
• Uses: 7-Oxabicyclo[2.2.1]hept-5-ene-2-carboxylic Acid is used in the study of UV and thermally triggered ring-opening metathesis polymerization.

Technology Process of 7-Oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

There total 1 articles about 7-Oxa-bicyclo[2.2.1]hept-5-ene-2-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:

furan (110-00-9) + triacetoxyborane (4887-24-5) + acrylic acid (79-10-7) → 7-oxabicyclo[2.2.1]hept-2-ene-endo-5-carboxylic acid (24363-23-3)

Guidance literature:

Reference yield: 82.0%

(+/-)-7-oxabicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid (24363-23-3,38263-45-5,38263-46-6,64589-22-6,90760-55-7,90760-56-8,117772-64-2) + benzenesulfenyl chloride (931-59-9) → (1R,2S,4S,5R,6S)-6-Hydroxy-5-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid (139277-16-0)

Guidance literature:

In chloroform; for 48h; 0 deg C to r.t.;

DOI:10.1021/jo00033a002

Reference yield:

(+/-)-7-oxabicyclo[2.2.1]hept-5-ene-2-exo-carboxylic acid (24363-23-3,38263-45-5,38263-46-6,64589-22-6,90760-55-7,90760-56-8,117772-64-2) → DL-(1,4/2,3,5)-1,4-diacetamido-5-acethoxymethyl-2,3-di-O-acetyl-2,3-cyclohexanediol

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / acetyl chloride / 3 h / Ambient temperature

2: 83 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / Ambient temperature

3: 12 percent / hydrogen bromide (20percent) / acetic acid / 36 h / 80 °C

4: 87 percent / sodium azide / 2-methoxy-ethanol; H₂O / 1.5 h / Heating

5: 1.) H₂ / 1.) Raney nickel / 1.) 3.4 kg/cm2, methanol, room t; 2.) methanol, room t.

With sodium azide; hydrogen bromide; hydrogen; acetyl chloride; 3-chloro-benzenecarboperoxoic acid; nickel; In dichloromethane; 2-methoxy-ethanol; water; acetic acid;

DOI:10.1016/0008-6215(88)85054-7

upstream raw materials:

furan

triacetoxyborane

acrylic acid

Downstream raw materials:

7-oxabicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid methyl ester

(1RS,2SR,4RS)-7-oxabicyclo[2.2.1]hept-5-ene-2-methanol

Benzoic acid (1R,2S,4R)-1-(7-oxa-bicyclo[2.2.1]hept-5-en-2-yl)methyl ester

(1R,2S,4S,5R,6S)-6-Hydroxy-5-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid