(2Z,6E,8E)-3-Acetoxy-5-benzenesulfonyl-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6,8-trienoic acid methyl ester

Base Information

• Chemical Name: (2Z,6E,8E)-3-Acetoxy-5-benzenesulfonyl-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6,8-trienoic acid methyl ester
• CAS No.: 80367-82-4
• Molecular Formula: C₂₈H₃₆O₆S
• Molecular Weight: 500.656
• Mol file: 80367-82-4.mol

Synonyms:

Chemical Property of (2Z,6E,8E)-3-Acetoxy-5-benzenesulfonyl-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6,8-trienoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2Z,6E,8E)-3-Acetoxy-5-benzenesulfonyl-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6,8-trienoic acid methyl ester

There total 2 articles about (2Z,6E,8E)-3-Acetoxy-5-benzenesulfonyl-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6,8-trienoic acid methyl ester 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:

E,Z-methyl 3-acetoxybutenoate (3666-79-3) → (2Z,6E,8E)-3-Acetoxy-5-benzenesulfonyl-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6,8-trienoic acid methyl ester (80367-82-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 30 percent / NBS, azobis(isobutyronitrile) / CCl₄ / Heating; Irradiation

2: 1.) MeLi, diisopropylamine / 1.) THF, Et₂O, from -78 deg C to 0 deg C, 10 min, 2.) THF, -78 deg C, 20 min

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); methyllithium; diisopropylamine; In tetrachloromethane;

DOI:10.1021/jo00342a001

Reference yield:

5-(2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-1-phenyl-sulphonyl-penta-2,4-diene (38987-91-6) + (E)-3-Acetoxy-4-bromo-but-2-enoic acid methyl ester (80367-80-2) → (2Z,6E,8E)-3-Acetoxy-5-benzenesulfonyl-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6,8-trienoic acid methyl ester (80367-82-4)

Guidance literature:

With methyllithium; diisopropylamine; Yield given. Multistep reaction; 1.) THF, Et₂O, from -78 deg C to 0 deg C, 10 min, 2.) THF, -78 deg C, 20 min;

DOI:10.1021/jo00342a001

Reference yield: 25.0%

(2Z,6E,8E)-3-Acetoxy-5-benzenesulfonyl-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6,8-trienoic acid methyl ester (80367-82-4) → methyl (all E)-7-methyl-3-acetoxy-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate (80367-71-1) + methyl 7-methyl-3-acetoxy-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-(2Z,4E,6E,8E)-2,4,6,8-nonatetraenoate (80408-66-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; for 0.166667h; Ambient temperature;

DOI:10.1021/jo00342a001

upstream raw materials:

5-(2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-1-phenyl-sulphonyl-penta-2,4-diene

(E)-3-Acetoxy-4-bromo-but-2-enoic acid methyl ester

E,Z-methyl 3-acetoxybutenoate

Downstream raw materials:

methyl (all E)-7-methyl-3-acetoxy-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate

methyl 7-methyl-3-acetoxy-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-(2Z,4E,6E,8E)-2,4,6,8-nonatetraenoate