Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 2,3-dimethyl-, (1S,2R,3R,4R)- (9CI)

Base Information

• Chemical Name: Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 2,3-dimethyl-, (1S,2R,3R,4R)- (9CI)
• CAS No.: 154279-12-6
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.221
• Mol file: 154279-12-6.mol

Synonyms:Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde,2,3-dimethyl-, (1S-exo)-

Chemical Property of Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 2,3-dimethyl-, (1S,2R,3R,4R)- (9CI)

Chemical Property:

• PSA: 17.07000
• LogP: 2.03360

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 2,3-dimethyl-, (1S,2R,3R,4R)- (9CI)

There total 32 articles about Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 2,3-dimethyl-, (1S,2R,3R,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: 99.0%

2-methylbut-2-enal (497-03-0) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (1S,2R,3S,4S)-2,3-dimethylbicyclo[2.2.1]hept-5-ene-2-carboxaldehyde (154279-12-6,509149-25-1,509149-30-8,509149-31-9)

Guidance literature:

With (R)-3,3'-bis(2-hydroxyphenyl)-2,2'-dihydroxy-1,1'-binaphthyl-boric acid; In tetrahydrofuran; dichloromethane; at -78 ℃; for 4h;

DOI:10.1021/ja00083a048

Reference yield: 92.0%

2-methyl-2-pentenal (1115-11-3) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (1RS,2SR,3RS,4SR)-2,3-dimethylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde (154279-12-6,509149-25-1,509149-30-8,509149-31-9)

Guidance literature:

With trifluorormethanesulfonic acid; ethyl 1,2-diazepane-1-carboxylate; In acetonitrile; at 20 ℃; for 4h; diastereoselective reaction;

DOI:10.1002/ejoc.201801009

Reference yield: 80.0%

2-methylbut-2-enal (497-03-0) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → 2,3-dimethylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde (154279-12-6,509149-25-1,509149-30-8,509149-31-9)

Guidance literature:

With C₃₃H₃₂BF₃NO₅P*2C₁₈BF₁₅; In dichloromethane; at -78 ℃; for 3h; stereoselective reaction; Molecular sieve;

DOI:10.1055/s-0035-1561362

upstream raw materials:

2-methyl-2-pentenal

cyclopenta-1,3-diene

2-methylbut-2-enal

(Z)-2-methyl-2-butenal

Downstream raw materials:

[(1RS,2SR,3RS,4SR)-2,3-dimethylbicyclo[2.2.1]hept-5-en-2-yl]methanol

[(1RS,2SR,3SR,4SR)-2,3-dimethylbicyclo[2.2.1]hept-5-en-2-yl]methanol