1-(4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one

Base Information

• Chemical Name: 1-(4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one
• CAS No.: 35734-61-3
• Molecular Formula: C13H20O2
• Molecular Weight: 208.301
• European Community (EC) Number: 260-430-1
• DSSTox Substance ID: DTXSID401314678
• Nikkaji Number: J385.672K,J267.130A
• Metabolomics Workbench ID: 49468
• Mol file: 35734-61-3.mol

Synonyms:3-hydroxy-beta-damascone

Chemical Property of 1-(4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one

Chemical Property:

• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 208.146329876
• Heavy Atom Count: 15
• Complexity: 321

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC(=O)C1=C(CC(CC1(C)C)O)C
• Isomeric SMILES: C/C=C/C(=O)C1=C(CC(CC1(C)C)O)C

Technology Process of 1-(4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one

There total 14 articles about 1-(4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-2-buten-1-one 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: 86.0%

allyllithium (3052-45-7) + Ethyl 2,6,6-trimethyl-4-hydroxy-1-cyclohexene-1-carboxylate → 3-hydroxymegastigma-5,8-dien-7-one (35734-61-3,56915-02-7)

Guidance literature:

In tetrahydrofuran; at -15 ℃; for 4h;

Reference yield: 86.0%

beta damascone (23726-91-2) → 3-hydroxymegastigma-5,8-dien-7-one (35734-61-3,56915-02-7) + (E)-1-(3-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)but-2-en-1-one

Guidance literature:

With ferredoxin reductase; [2Fe-2S] ferredoxin; cytochrome P₄₅₀ 101B₁ enzyme from Novosphingobium aromaticivorans DSM₁₂₄₄₄; oxygen; NADH; bovine liver catalase; In aq. buffer; at 30 ℃; pH=7.4; regioselective reaction; Catalytic behavior; Kinetics; Enzymatic reaction;

DOI:10.1039/c4ra14010a

Reference yield: 78.0%

(3RS,5RS,6SR,9SR)-megastigm-7-yne-3,6,9-triol (32469-38-8,125810-91-5) → Damascenon (23726-93-4) + 3-hydroxymegastigma-5,8-dien-7-one (35734-61-3,56915-02-7) + 9-hydroxymegastigma-3,5-dien-7-one (41436-47-9) + 3-Hydroxy-1-(4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-butan-1-one (125791-43-7)

Guidance literature:

With sulfuric acid; In ethanol; water; at 100 ℃; for 1.33h; Product distribution; var. reaction times, temperatures; also for megastigm-5-en-7-yne-3,9-diol ⁽¹⁰⁾;

upstream raw materials:

allyllithium

3-(4-Acetoxy-2-hydroxy-2,6,6-trimethylcyclohexylidene)-1-methylprop-2-enyl 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranoside

6,7-Megastigmadiene-3,5,9-triol

(3RS,5RS,6SR,9SR)-megastigm-7-yne-3,6,9-triol

Downstream raw materials:

(Z)-megastigma-4,8-diene-3,7-dione

(E)-megastigma-4,8-diene-3,7-dione

(+/-)-1-(2,6,6-trimethyl-4-hydroxycyclohexenyl)-1,3-butanedione

3-Hydroxy-8,9-dihydro-β-damascon

Refernces

• 1、 Hall, Emma A.,Bell, Stephen G.. "The efficient and selective biocatalytic oxidation of norisoprenoid and aromatic substrates by CYP101B1 from Novosphingobium aromaticivorans DSM12444". . p. 5762 - 5773. Retrieved 2015/03/05.
• 2、 Skouroumounis, George K.,Sefton, Mark A.. "Acid-catalyzed hydrolysis of alcohols and their β-D-glucopyranosides". . p. 2033 - 2039. Retrieved 2007/10/03.