endo-(1R,2S,3S,4S)-3-(4-methoxyphenyl)bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde

Base Information

• Chemical Name: endo-(1R,2S,3S,4S)-3-(4-methoxyphenyl)bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde
• CAS No.: 1301133-89-0
• Molecular Formula: C₁₅H₁₆O₂
• Molecular Weight: 228.291
• Mol file: 1301133-89-0.mol

Synonyms:endo-(1R,2S,3S,4S)-3-(4-methoxyphenyl)bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde

Chemical Property of endo-(1R,2S,3S,4S)-3-(4-methoxyphenyl)bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of endo-(1R,2S,3S,4S)-3-(4-methoxyphenyl)bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde

There total 9 articles about endo-(1R,2S,3S,4S)-3-(4-methoxyphenyl)bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde 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:

4-methoxy-trans-cinnamaldehyde (24680-50-0,71277-11-7,1963-36-6) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (1S,2S,3S,4R)-3‐(4-methoxyphenyl)bicyclo[2.2.1]hept‐5‐ene‐2‐carbaldehyde (1069084-47-4) + 3‐(4-methoxyphenyl)bicyclo[2.2.1]hept‐5‐ene‐2‐carbaldehyde (1032817-87-0) + endo-(1S,2R,3R,4R)-3-(4-methoxyphenyl)bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde (1032817-88-1) + endo-(1R,2S,3S,4S)-3-(4-methoxyphenyl)bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde (1301133-89-0)

Guidance literature:

With perchloric acid; (2S,2'S,3R,3'R)-3,3'-bis(benzyloxy)-2,2'-bipyrrolidine; In water; at 20 ℃; for 3.5h; optical yield given as %ee; enantioselective reaction;

DOI:10.1016/j.tet.2010.03.042

Reference yield:

4-methoxycinnamaldehyde (1963-36-6) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (1S,2S,3S,4R)-3‐(4-methoxyphenyl)bicyclo[2.2.1]hept‐5‐ene‐2‐carbaldehyde (1069084-47-4) + 3‐(4-methoxyphenyl)bicyclo[2.2.1]hept‐5‐ene‐2‐carbaldehyde (1032817-87-0) + endo-(1R,2S,3S,4S)-3-(4-methoxyphenyl)bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde (1301133-89-0)

Guidance literature:

With 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide immobilized MacMillan imidazolidine catalyst in silica bed; In tert-Amyl alcohol; at 20 ℃; for 46h; optical yield given as %ee; enantioselective reaction;

DOI:10.1002/adsc.200900865

Reference yield:

4-methoxy-trans-cinnamaldehyde (24680-50-0,71277-11-7,1963-36-6) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → 3‐(4-methoxyphenyl)bicyclo[2.2.1]hept‐5‐ene‐2‐carbaldehyde (1032817-87-0) + endo-(1R,2S,3S,4S)-3-(4-methoxyphenyl)bicyclo[2.2.1]hept-5-ene-2-carboxaldehyde (1301133-89-0)

Guidance literature:

With perchloric acid; C₅₇H₇₆N₈O₈; In water; acetonitrile; at 25 ℃; for 24h; Overall yield = 82 %; Overall yield = 187.2 mg; stereoselective reaction;

upstream raw materials:

4-methoxy-trans-cinnamaldehyde

cyclopenta-1,3-diene

4-methoxycinnamaldehyde

3-(4-methoxyphenyl)propional