(2E,6E)-10-hydroxy-3,7,11-trimethyldodeca-2,6,11-trienyl acetate

Base Information

• Chemical Name: (2E,6E)-10-hydroxy-3,7,11-trimethyldodeca-2,6,11-trienyl acetate
• CAS No.: 120733-46-2
• Molecular Formula: C₁₇H₂₈O₃
• Molecular Weight: 280.408
• Mol file: 120733-46-2.mol

Synonyms:(2E,6E)-10-hydroxy-3,7,11-trimethyldodeca-2,6,11-trienyl acetate

Chemical Property of (2E,6E)-10-hydroxy-3,7,11-trimethyldodeca-2,6,11-trienyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,6E)-10-hydroxy-3,7,11-trimethyldodeca-2,6,11-trienyl acetate

There total 2 articles about (2E,6E)-10-hydroxy-3,7,11-trimethyldodeca-2,6,11-trienyl acetate 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: 40.0%

10,11-epoxyfarnesyl acetate (50502-44-8) → (2E,6E)-10-hydroxy-3,7,11-trimethyldodeca-2,6,11-trienyl acetate (120733-46-2) + (E)-5-((1RS,3SR)-3-hydroxy-2,2-dimethyl-6-methylenecyclohexyl)-3-methylpent-2-enyl acetate + (2SR,4aSR,5SR,8aRS)-5-acetoxymethyl-2-hydroxy-1,1,4a-trimethyl-6-methylene-decahydronaphthalene

Guidance literature:

10,11-epoxyfarnesyl acetate; With 2,4,6-trimethyl-pyridine; manganese; chloro-trimethyl-silane; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; for 8h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h; Further stages.;

DOI:10.1002/chem.200305647

Reference yield:

10,11-epoxyfarnesyl acetate (50502-44-8) → (E)-5-((1RS,5SR)-5-hydroxy-2,6,6-trimethylcyclohex-2-enyl)-3-methylpent-2-enyl acetate + (E)-3-methyl-5-((1RS,2SR,4SR)-1,3,3-trimethyl-7-oxa-bicyclo[2.2.1]heptan-2-yl)pent-2-enyl acetate + (2E,6E)-10-hydroxy-3,7,11-trimethyldodeca-2,6,11-trienyl acetate (120733-46-2) + (E)-5-((1RS,3SR)-3-hydroxy-2,2-dimethyl-6-methylenecyclohexyl)-3-methylpent-2-enyl acetate

Guidance literature:

With zeolite NaY; In hexane; at 20 ℃; for 0.25h; Title compound not separated from byproducts.;

DOI:10.1021/ol062798i

Reference yield:

(2E,6E)-10-hydroxy-3,7,11-trimethyldodeca-2,6,11-trienyl acetate (120733-46-2) → (E)-6,10-dihydroxy-3,11-dimethyl-7-methylenedodeca-2,11-dienyl acetate (1335012-91-3) + rac-[(1R,2S,3S)-3-hydroxy-2-(3-hydroxy-4-methylpent-4-enyl)-2-methyl-6-methylenecyclohexyl]methyl acetate

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1H-imidazole / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C / Inert atmosphere

3.1: 2,4,6-trimethyl-pyridine; manganese; chloro-trimethyl-silane; bis(cyclopentadienyl)-titanium(III) chloride / tetrahydrofuran / 0.83 h / 20 °C / Inert atmosphere

3.2: 1 h / 20 °C / Inert atmosphere

With 1H-imidazole; 2,4,6-trimethyl-pyridine; manganese; chloro-trimethyl-silane; bis(cyclopentadienyl)-titanium(III) chloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1002/ejoc.201100400

upstream raw materials:

10,11-epoxyfarnesyl acetate

Downstream raw materials:

(E)-6,10-dihydroxy-3,11-dimethyl-7-methylenedodeca-2,11-dienyl acetate

Refernces

• 1、 Tsangarakis, Constantinos,Raptis, Christos,Arkoudis, Elias,Stratakis, Manolis. "Zeolite NaY-promoted monocyclization of epoxy polyene terpenes: A unique route for the direct synthesis of incompletely cyclized naturally occurring terpenols". body text. p. 1587 - 1600. Retrieved 2009/07/30.