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

Base Information

• Chemical Name: Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 2-ethyl-, (1S,2R,4S)- (9CI)
• CAS No.: 154279-11-5
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.221
• Mol file: 154279-11-5.mol

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

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

Chemical Property:

• PSA: 0.00000
• LogP: 0.00000

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 24 articles about Bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde, 2-ethyl-, (1S,2R,4S)- (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%

ethylacrolein (922-63-4) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (1R,2S,4R)-bicyclo[2.2.1]hept-5-ene-2-ethyl-2-carboxaldehyde (136577-69-0,154279-11-5,166020-89-9,174757-35-8)

Guidance literature:

With C₅₀H₃₁BF₁₅NO₂*C₁₈BF₁₅; In dichloromethane; at -78 ℃; for 3h; stereoselective reaction; Molecular sieve;

DOI:10.1055/s-0035-1561362

Reference yield: 68.0%

ethylacrolein (922-63-4) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (1S,2R,4S)-bicyclo[2.2.1]hept-5-ene-2-ethyl-2-carboxaldehyde (136577-69-0,154279-11-5,166020-89-9,174757-35-8)

Guidance literature:

With trifluorormethanesulfonic acid; (R)-3,3'-bis(3,5-di-tert-butylphenyl)-1,1'-binaphthyl-2,2'-diamine; In 1,3,5-trimethyl-benzene; at -20 ℃; for 48h; optical yield given as %ee; enantioselective reaction;

DOI:10.1039/b819034h

Reference yield:

ethylacrolein (922-63-4) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (1S,2R,4S)-bicyclo[2.2.1]hept-5-ene-2-ethyl-2-carboxaldehyde (136577-69-0,154279-11-5,166020-89-9,174757-35-8) + (1R,2S,4R)-bicyclo[2.2.1]hept-5-ene-2-ethyl-2-carboxaldehyde (136577-69-0,154279-11-5,166020-89-9,174757-35-8)

Guidance literature:

With (R)-3,3'-bis(2-hydroxyphenyl)-2,2'-dihydroxy-1,1'-binaphthyl-boric acid; In tetrahydrofuran; dichloromethane; at -78 ℃; for 4h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/ja00083a048

upstream raw materials:

ethylacrolein

cyclopenta-1,3-diene