[(E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-yl] acetate

Base Information

• Chemical Name: [(E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-yl] acetate
• CAS No.: 783324-41-4
• Molecular Formula: C15H24O2
• Molecular Weight: 236.354
• European Community (EC) Number: 257-738-3
• Nikkaji Number: J160.380I
• Mol file: 783324-41-4.mol

Synonyms:52210-18-1;alpha-Ionol acetate;.alpha. Ionyl acetate;.alpha.-Ionol acetate;3-06-00-00402 (Beilstein Handbook Reference);SCHEMBL3505890;3 - (2,6,6 - trimethyl - 2 - cyclohexen - 1 - yl)propen - 1 - yl acetate;WHHAWKIPTSGTNC-CMDGGOBGSA-N;4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-olacetate;[(E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-yl] acetate;NS00012650;(E)-4-(2,6,6-trimethylcyclohex-2-enyl)but-3-en-2-yl acetate;(2E)-1-Methyl-3-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-propenyl acetate #

Chemical Property of [(E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-yl] acetate

Chemical Property:

• PSA: 57.53000
• LogP: 3.39680
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 236.177630004
• Heavy Atom Count: 17
• Complexity: 337

Purity/Quality:

Acetylα-Ionol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCCC(C1C=CC(C)OC(=O)C)(C)C
• Isomeric SMILES: CC1=CCCC(C1/C=C/C(C)OC(=O)C)(C)C
• Uses: Acetyl α-Ionol is an intermediate in synthesizing Tabanone (T003450), found in oils of Trifolium pratense L. and is a potential natural antioxidant.

Technology Process of [(E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-yl] acetate

There total 4 articles about [(E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-yl] 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: 100.0%

alpha-ionol (25312-34-9) + acetic anhydride (108-24-7) → (2E)-1-methyl-3-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-propenyl acetate (783324-41-4,52210-18-1)

Guidance literature:

With iodine; for 0.5h; Ambient temperature;

DOI:10.1039/a605061a

Reference yield:

alpha-ionone (127-41-3,6901-97-9,14398-36-8,24190-29-2,30685-95-1,31798-12-6,52340-45-1,67529-94-6,67529-95-7) → (2E)-1-methyl-3-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-propenyl acetate (783324-41-4,52210-18-1)

Guidance literature:

Multi-step reaction with 2 steps

1: isopropyl alcohol

2: pyridine

With pyridine; isopropyl alcohol;

Reference yield:

(+)-(R)-α-Ionon (24190-29-2) → (2E)-1-methyl-3-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-propenyl acetate (783324-41-4,52210-18-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / sodium borohydride / methanol / 1.) 1 h, 0 deg C, 2) 3 h, room temperature

2: 95 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / Ambient temperature

With dmap; sodium tetrahydroborate; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jo00290a057

upstream raw materials:

alpha-ionol

acetic anhydride

acetyl chloride

(+)-(R)-α-Ionon

Downstream raw materials:

(E)-1-(2,6,6-trimethylcyclohex-2-en-1-yl)-3-(trimethylsilyl)but-1-ene

9-hydroxymegastigma-4,7-dien-3-one

(E)-4-(2,2-Dimethyl-6-methylene-cyclohexyl)-but-3-en-2-ol

γ-ionone