Isoeugenyl methyl ether

Base Information

• Chemical Name: Isoeugenyl methyl ether
• CAS No.: 6380-24-1
• Molecular Formula: C11H14O2
• Molecular Weight: 178.231
• European Community (EC) Number: 202-224-6
• UNII: 64DPK8DS6F
• DSSTox Substance ID: DTXSID101026531
• Nikkaji Number: J15.691D
• Wikipedia: Methyl isoeugenol,Methyl_isoeugenol
• Wikidata: Q27122111
• Metabolomics Workbench ID: 49414
• ChEMBL ID: CHEMBL1164609
• Mol file: 6380-24-1.mol

Synonyms:isomethyleugenol;isomethyleugenol, (E)-isomer;isomethyleugenol, (Z)-isomer;methyl isoeugenol;methylisoeugenol;trans-isomethyleugenol

Chemical Property of Isoeugenyl methyl ether

Chemical Property:

• Melting Point: 70°C
• Refractive Index: 1.5616 (estimate)
• Boiling Point: 270.5°C (estimate)
• PSA: 18.46000
• Density: 1.0521
• LogP: 2.73690
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 178.099379685
• Heavy Atom Count: 13
• Complexity: 166

Purity/Quality:

98%min ^*data from raw suppliers

(Z)-Methylisoeugenol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC1=CC(=C(C=C1)OC)OC
• Isomeric SMILES: C/C=C\C1=CC(=C(C=C1)OC)OC
• Uses: (Z)-Methylisoeugenol is a useful building block used in the sustainable preparation of asarone. (Z)-Methylisoeugenol has been extracted from the essential oils of the Piper genus, and shows antifungal activity against dermatophytes and fungi.

Technology Process of Isoeugenyl methyl ether

There total 17 articles about Isoeugenyl methyl ether 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: 78.0%

1,2-dimethoxy-4-(2-propenyl)benzene (93-15-2) → (Z)-1,2-dimethoxy-4-(prop-1-en-1-yl)benzene (6380-24-1) + 1,2-dimethoxy-4-(E)-propenylbenzene (6379-72-2)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In methanol; at 60 ℃; Inert atmosphere;

DOI:10.1021/jacs.8b01815

Reference yield:

ethyltriphenylphosphonium bromide (1530-32-1) + 3,4-dimethoxy-benzaldehyde (120-14-9) → (Z)-1,2-dimethoxy-4-(prop-1-en-1-yl)benzene (6380-24-1) + 1,2-dimethoxy-4-(E)-propenylbenzene (6379-72-2)

Guidance literature:

ethyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; cyclohexane; at 0 ℃; for 4h; Inert atmosphere;

3,4-dimethoxy-benzaldehyde; In tetrahydrofuran; hexane; cyclohexane; at 20 ℃; for 10h; Overall yield = 92 %; Overall yield = 1.64 g; Inert atmosphere;

DOI:10.1002/anie.201208082

Reference yield:

methyl-triphenylphosphonium iodide (2065-66-9) + 3,4-dimethoxy-benzaldehyde (120-14-9) → (Z)-1,2-dimethoxy-4-(prop-1-en-1-yl)benzene (6380-24-1) + 1,2-dimethoxy-4-(E)-propenylbenzene (6379-72-2)

Guidance literature:

methyl-triphenylphosphonium iodide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 1h; Inert atmosphere;

3,4-dimethoxy-benzaldehyde; In tetrahydrofuran; hexane; at 20 ℃; for 2h; Overall yield = 55 %;

DOI:10.1021/acs.orglett.8b02541

upstream raw materials:

1,2-dimethoxy-4-(prop-1-yn-1-yl)benzene

cis-isoeugenol

dimethyl sulfate

1,2-dimethoxy-4-(E)-propenylbenzene

Downstream raw materials:

1,2-dimethoxy-4-(E)-propenylbenzene

4-propyl-1,2-dimethoxybenzene

5,7-dichloro-4-(3,4-dimethoxyphenyl)-3-methyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid ethyl ester

3,4-dimethoxy-benzaldehyde

Refernces

• 1、 Liu, Hongmei,Xu, Man,Cai, Cheng,Chen, Jianhui,Gu, Yugui,Xia, Yuanzhi. "Cobalt-Catalyzed Z to e Isomerization of Alkenes: An Approach to (E)-β-Substituted Styrenes". supporting information. p. 1193 - 1198. Retrieved 2020/02/04.
• 2、 Liu, Xufang,Zhang, Wei,Wang, Yujie,Zhang, Ze-Xin,Jiao, Lei,Liu, Qiang. "Cobalt-Catalyzed Regioselective Olefin Isomerization under Kinetic Control". supporting information. p. 6873 - 6882. Retrieved 2018/05/30.