dimethyl 2-[(3E,6E)-1-methyl-5-oxo-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,6-heptatrienyl]malonate

Base Information

• Chemical Name: dimethyl 2-[(3E,6E)-1-methyl-5-oxo-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,6-heptatrienyl]malonate
• CAS No.: 419550-36-0
• Molecular Formula: C₂₂H₃₀O₅
• Molecular Weight: 374.477
• Mol file: 419550-36-0.mol

Synonyms:dimethyl 2-[(3E,6E)-1-methyl-5-oxo-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,6-heptatrienyl]malonate

Chemical Property of dimethyl 2-[(3E,6E)-1-methyl-5-oxo-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,6-heptatrienyl]malonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl 2-[(3E,6E)-1-methyl-5-oxo-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,6-heptatrienyl]malonate

There total 2 articles about dimethyl 2-[(3E,6E)-1-methyl-5-oxo-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,6-heptatrienyl]malonate 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: 65.0%

β-ionone (105593-28-0) + dimethyl 2-[(2E)-3-(dimethylamino)-1-methyl-2-propenylidene]malonate (419550-09-7) → dimethyl 2-[(3E,6E)-1-methyl-5-oxo-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,6-heptatrienyl]malonate (419550-36-0)

Guidance literature:

With diisopropylamine; In 1,2-dimethoxyethane; hexane; for 2h; Heating;

DOI:10.1002/ejoc.200300029

Reference yield:

dimethyl isopropylidenemalonate (22035-53-6) → dimethyl 2-[(3E,6E)-1-methyl-5-oxo-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,6-heptatrienyl]malonate (419550-36-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / methanol / 18 h / 95 °C

2: 65 percent / iPr₂NH / 1,2-dimethoxy-ethane; hexane / 2 h / Heating

With diisopropylamine; In methanol; 1,2-dimethoxyethane; hexane;

DOI:10.1002/ejoc.200300029

Reference yield: 69.0%

methylmagnesium bromide (75-16-1) + dimethyl 2-[(3E,6E)-1-methyl-5-oxo-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3,6-heptatrienyl]malonate (419550-36-0) → methyl 14-(methoxycarbonyl)-retro-retionate

Guidance literature:

In tetrahydrofuran; at -10 ℃; for 0.5h;

DOI:10.1002/ejoc.200300029

upstream raw materials:

β-ionone

dimethyl 2-[(2E)-3-(dimethylamino)-1-methyl-2-propenylidene]malonate

dimethyl isopropylidenemalonate

Downstream raw materials:

13-cis-retinoic acid

all-trans-retinoic-acid