Isoeugenyl acetate

Base Information

• Chemical Name: Isoeugenyl acetate
• CAS No.: 5912-87-8
• Molecular Formula: C12H14O3
• Molecular Weight: 206.241
• European Community (EC) Number: 813-782-0,202-236-1
• NSC Number: 46121
• UNII: 7XK69TOK59
• DSSTox Substance ID: DTXSID601020590
• Nikkaji Number: J34.562H,J984.680H
• Wikidata: Q27159265
• RXCUI: 2393779
• Metabolomics Workbench ID: 45449
• ChEMBL ID: CHEMBL1609480
• Mol file: 5912-87-8.mol

Synonyms:2-methoxy-4-prop-1-enylphenyl acetate;Isoeugenol acetate;Isoeugenyl acetate

Chemical Property of Isoeugenyl acetate

Chemical Property:

• Vapor Pressure: 0.07Pa at 25℃
• Melting Point: 80.5°C
• Refractive Index: 1.5052 (estimate)
• Boiling Point: 282.5°C (estimate)
• PSA: 35.53000
• Density: 1.0251
• LogP: 2.65360
• Solubility.: soluble in Methanol
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 206.094294304
• Heavy Atom Count: 15
• Complexity: 235

Purity/Quality:

99.9% ^*data from raw suppliers

1-Acetoxy-2-methoxy-4-[(E)-1-propenyl]benzene >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Isoeugenyl acetate

There total 16 articles about Isoeugenyl 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: 97.0%

eugenol acetate (93-28-7) → (E)-1-(4-acetoxy-3-methoxyphenyl)-1-propene (5912-87-8,93-29-8)

Guidance literature:

With palladium(II) trifluoroacetate; 2-(diphenylphosphino)pyridine; 2-fluoroethanol; In 1,2-dichloro-ethane; at 25 - 27 ℃; for 24h; stereoselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.0c00168

Reference yield: 84.0%

eugenol acetate (93-28-7) → 3-methoxy-4-acetoxy-1-cis-propenyl-benzene (97412-23-2,93-29-8) + (E)-1-(4-acetoxy-3-methoxyphenyl)-1-propene (5912-87-8,93-29-8)

Guidance literature:

With nickel(II) iodide; 6,6'-dimethyl-2,2'-bipyridine; phosphonic acid diethyl ester; zinc; In N,N-dimethyl acetamide; at 35 ℃; for 24h;

Reference yield: 80.0%

9,10-dihydro-9,10-dihydroxyanthracene (58343-58-1) + 2-Methoxy-4-[2-(2-methoxy-phenoxy)-prop-(Z)-ylidene]-cyclohexa-2,5-dienone (36382-85-1,85557-40-0) → 2-methoxyphenyl acetate (613-70-7) + (E)-1-(4-acetoxy-3-methoxyphenyl)-1-propene (5912-87-8,93-29-8) + threo-1-(3-methoxy-4-acetoxyphenyl)-1-(10-hydroxy-9-oxoanthracen-10-yl)-2-(2-methoxyphenoxy)propane (82247-07-2)

Guidance literature:

With pyridine; In chloroform; Yields of byproduct given; Ambient temperature;

DOI:10.1021/jo00139a020

upstream raw materials:

acetamide

2-methoxy-4-propenylphenol

acetic anhydride

9,10-dihydro-9,10-dihydroxyanthracene

Downstream raw materials:

(+/-)-3-methoxy-4-acetoxy-1-(threo-1.2-dibromo-propyl)-benzene

(+/-)-3-methoxy-4-acetoxy-1-(erythro-1.2-dibromo-propyl)-benzene

1-acetoxy-2-methoxy-4-(2-nitro-1-nitroso-propyl)-benzene

vanillin

Refernces

• 1、 Ren, Wenlong,Sun, Fei,Chu, Jianxiao,Shi, Yian. "A Pd-Catalyzed Site-Controlled Isomerization of Terminal Olefins". supporting information. p. 1868 - 1873. Retrieved 2020/03/03.
• 2、 González-Fernández, Rebeca,Crochet, Pascale,Cadierno, Victorio. "Hydrophilic (ν6-Arene)-Ruthenium(II) Complexes with P-OH ligands as catalysts for the isomerization of allylbenzenes and C-H bond arylation reactions in water". . p. 3696 - 3706. Retrieved 2019/10/11.