Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 2-methyl-, (1R,2R,4R)-(9CI)

Base Information

• Chemical Name: Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 2-methyl-, (1R,2R,4R)-(9CI)
• CAS No.: 176774-82-6
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.193
• DSSTox Substance ID: DTXSID80474508
• Nikkaji Number: J1.416.443J
• Wikidata: Q82304560
• Mol file: 176774-82-6.mol

Synonyms:176774-82-6;Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 2-methyl-, (1R,2R,4R)- (9CI);(1R,2R,4R)-2-METHYLBICYCLO[2.2.1]HEPT-5-ENE-2-CARBOXYLIC ACID;CTK0H1103;DTXSID80474508;Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 2-methyl-, (1R,2R,4R)-(9CI)

Chemical Property of Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 2-methyl-, (1R,2R,4R)-(9CI)

Chemical Property:

• PSA: 37.30000
• LogP: 1.67330
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 152.083729621
• Heavy Atom Count: 11
• Complexity: 232

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC2CC1C=C2)C(=O)O
• Isomeric SMILES: C[C@]1(C[C@H]2C[C@@H]1C=C2)C(=O)O

Technology Process of Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 2-methyl-, (1R,2R,4R)-(9CI)

There total 3 articles about Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 2-methyl-, (1R,2R,4R)-(9CI) 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: 96.0%

<3R-(3α,3aβ,5α,6β,6aβ)>-hexahydro-6-iodo-3-methyl-3,5-methano-2H-cyclopentafuran-2-one (13432-80-9) → (1R,2R,4R)-2-Methyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (176774-82-6)

Guidance literature:

With acetic acid; zinc; for 3h; Ambient temperature;

DOI:10.1021/ja9525317

Reference yield:

poly(methacrylic acid) (79-41-4,25087-26-7,50867-57-7) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (1S-endo)-2-methylbicyclo<2.2.1>hept-5-ene-2-carboxylic acid (176774-74-6) + (1S)-endo-2-methylbicyclo<2.2.1>hept-5-ene-2-carboxylic acid (92007-58-4) + (1R-exo)-2-methylbicyclo<2.2.1>hept-5-ene-2-carboxylic acid (575465-35-9) + (1R,2R,4R)-2-Methyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (176774-82-6)

Guidance literature:

at 40 ℃; for 24h;

Reference yield:

(1R,4R)-2-Methyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid → (1R,2R,4R)-2-Methyl-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (176774-82-6)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH, I₂, KI, NaHCO₃ / 0.67 h / 0 °C

2: 96 percent / Zn, AcOH / 3 h / Ambient temperature

With sodium hydroxide; iodine; sodium hydrogencarbonate; acetic acid; potassium iodide; zinc;

DOI:10.1021/ja9525317

upstream raw materials:

<3R-(3α,3aβ,5α,6β,6aβ)>-hexahydro-6-iodo-3-methyl-3,5-methano-2H-cyclopentafuran-2-one

poly(methacrylic acid)

cyclopenta-1,3-diene