7-benzyloxy-8-methoxy-12-methyl-12-aza-benzo[h]spiro[5.6]dodec-1-ene-3,11-dione

Base Information

• Chemical Name: 7-benzyloxy-8-methoxy-12-methyl-12-aza-benzo[h]spiro[5.6]dodec-1-ene-3,11-dione
• CAS No.: 811819-72-4
• Molecular Formula: C₂₄H₂₅NO₄
• Molecular Weight: 391.467
• Mol file: 811819-72-4.mol

Synonyms:7-benzyloxy-8-methoxy-12-methyl-12-aza-benzo[h]spiro[5.6]dodec-1-ene-3,11-dione

Chemical Property of 7-benzyloxy-8-methoxy-12-methyl-12-aza-benzo[h]spiro[5.6]dodec-1-ene-3,11-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-benzyloxy-8-methoxy-12-methyl-12-aza-benzo[h]spiro[5.6]dodec-1-ene-3,11-dione

There total 13 articles about 7-benzyloxy-8-methoxy-12-methyl-12-aza-benzo[h]spiro[5.6]dodec-1-ene-3,11-dione 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: 95.0%

9-benzyloxy-10-methoxy-14-methyl-1,4-dioxa-14-aza-benzo[j]dispiro[4.2.6.2]hexadec-6-en-13-one (811819-69-9) → 7-benzyloxy-8-methoxy-12-methyl-12-aza-benzo[h]spiro[5.6]dodec-1-ene-3,11-dione (811819-72-4)

Guidance literature:

With silica gel; In methanol; at 20 ℃;

DOI:10.1016/j.tet.2004.09.044

Reference yield:

methanesulfonic acid 2-(1,4-dioxaspiro[4,5]dec-7-en-8-yl)ethyl ester (811819-77-9) → 7-benzyloxy-8-methoxy-12-methyl-12-aza-benzo[h]spiro[5.6]dodec-1-ene-3,11-dione (811819-72-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 90 percent / Et₃N / tetrahydrofuran; H₂O / Heating

2.1: SOCl₂ / tetrahydrofuran / 0.5 h / -78 °C

2.2: 73 percent / Et₃N / tetrahydrofuran / -40 - 20 °C

3.1: 28 percent / PPh₃; K₂CO₃ / Pd(OAc)2 / acetonitrile / 120 h / 130 °C

4.1: 95 percent / SiO₂ / methanol / 20 °C

With thionyl chloride; silica gel; potassium carbonate; triethylamine; triphenylphosphine; palladium diacetate; In tetrahydrofuran; methanol; water; acetonitrile; 3.1: Heck cyclization;

DOI:10.1016/j.tet.2004.09.044

Reference yield:

3-benzyloxy-2-iodo-4-methoxybenzoic acid (811819-63-3) → 7-benzyloxy-8-methoxy-12-methyl-12-aza-benzo[h]spiro[5.6]dodec-1-ene-3,11-dione (811819-72-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: SOCl₂ / tetrahydrofuran / 0.5 h / -78 °C

1.2: 73 percent / Et₃N / tetrahydrofuran / -40 - 20 °C

2.1: 28 percent / PPh₃; K₂CO₃ / Pd(OAc)2 / acetonitrile / 120 h / 130 °C

3.1: 95 percent / SiO₂ / methanol / 20 °C

With thionyl chloride; silica gel; potassium carbonate; triphenylphosphine; palladium diacetate; In tetrahydrofuran; methanol; acetonitrile; 2.1: Heck cyclization;

DOI:10.1016/j.tet.2004.09.044

upstream raw materials:

9-benzyloxy-10-methoxy-14-methyl-1,4-dioxa-14-aza-benzo[j]dispiro[4.2.6.2]hexadec-6-en-13-one

methanesulfonic acid 2-(1,4-dioxaspiro[4,5]dec-7-en-8-yl)ethyl ester

3-benzyloxy-2-iodo-4-methoxybenzoic acid

3-benzyloxy-N-[2-(1,4-dioxaspiro[4,5]dec-7-en-8-yl)ethyl]-2-iodo-4-methoxy-N-methyl-benzamide