Methyl (E)-3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)-2-pentenoate

Base Information

• Chemical Name: Methyl (E)-3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)-2-pentenoate
• CAS No.: 4179-00-4
• Molecular Formula: C₁₆H₂₆O₂
• Molecular Weight: 250.381
• Mol file: 4179-00-4.mol

Synonyms:Methyl (E)-3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)-2-pentenoate

Chemical Property of Methyl (E)-3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)-2-pentenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl (E)-3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)-2-pentenoate

There total 10 articles about Methyl (E)-3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)-2-pentenoate 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: 100.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (E) 3-Methyl-5-(2,2,6-trimethylcyclohexen-1-yl)-2-pentenoic Acid (4211-33-0) → Methyl (E)-3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)-2-pentenoate (4179-00-4)

Guidance literature:

In diethyl ether;

DOI:10.1055/s-1982-29808

Reference yield: 86.0%

methyl (E,E)-farnesoate (3675-00-1) → Methyl (E)-3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)-2-pentenoate (4179-00-4) + (+/-)-drim-7-en-11-oic acid methyl ester (34053-22-0,38142-33-5,64750-23-8,71493-11-3,82462-60-0,105479-55-8,111319-83-6)

Guidance literature:

With fluorosulphonic acid; 1-butyl-3-methylimidazolium Tetrafluoroborate; In dichloromethane; at -45 ℃; for 0.5h;

DOI:10.1007/s10600-006-0175-6

Reference yield:

4-(1-Hydroxy-2,2,6-trimethylcyclohexyl)-3-butyn-2-ol (41641-09-2) → Methyl (E)-3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)-2-pentenoate (4179-00-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / H₂ / Raney nickel W₅ / ethanol / 24 h / 120 °C / 38000 Torr

2: 96 percent / H₂SO₄ aq / methanol / 2 h / Ambient temperature

3: 90 percent / Na₂Cr₂O₇*H₂O, H₂SO₄ conc. / benzene; H₂O; acetic acid / Ambient temperature

4: 1.) NaH / 1.) THF, room temp., 1 h, 2.) THF, room temp., 18 h

5: 89 percent / 1.) KOH / ethanol; H₂O / 18 h / Heating

6: 100 percent / diethyl ether

With potassium hydroxide; sodium dichromate; sulfuric acid; hydrogen; sodium hydride; Raney nickel W₅; In methanol; diethyl ether; ethanol; water; acetic acid; benzene;

DOI:10.1055/s-1982-29808

upstream raw materials:

diazomethane

diethoxyphosphoryl-acetic acid ethyl ester

4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on

(E) 3-Methyl-5-(2,2,6-trimethylcyclohexen-1-yl)-2-pentenoic Acid

Downstream raw materials:

Bicyclofarnesic acid

4-[(3Z,7E)-4-Dimethoxymethyl-1-(1-ethoxy-ethoxy)-8-methyl-10-(2,6,6-trimethyl-cyclohex-1-enyl)-deca-3,7-dienyl]-5-hydroxy-5H-furan-2-one

{4-[(3Z,7E)-4-Dimethoxymethyl-1-(1-ethoxy-ethoxy)-8-methyl-10-(2,6,6-trimethyl-cyclohex-1-enyl)-deca-3,7-dienyl]-furan-2-yl}-trimethyl-silane

manoalide-2-methyl ether

Refernces

• 1、 Grin'ko,Kul'chitskii,Ungur,Vlad. "Superacid cyclization of certain aliphatic sesquiterpene derivatives in ionic liquids". . p. 439 - 441. Retrieved 2008/02/07.