methyl (2E)-3-[4-(benzyloxy)phenyl]prop-2-enoate

Base Information

• Chemical Name: methyl (2E)-3-[4-(benzyloxy)phenyl]prop-2-enoate
• CAS No.: 84184-51-0
• Molecular Formula: C17H16O3
• Molecular Weight: 268.312
• DSSTox Substance ID: DTXSID90420692
• Nikkaji Number: J988.082H
• Wikidata: Q82231998
• Mol file: 84184-51-0.mol

Synonyms:84184-51-0;methyl (2E)-3-[4-(benzyloxy)phenyl]prop-2-enoate;Methyl 4-Benzyloxy Cinnamate;methyl (E)-3-(4-phenylmethoxyphenyl)prop-2-enoate;(2E)-3-[4-(Phenylmethoxy)phenyl]-2-propenoic Acid Methyl Ester;SCHEMBL2776601;DTXSID90420692;STL480809;AKOS000295934;MS-10994;4-(Benzyloxy)benzeneacrylic acid methyl ester;methyl (2e)-3-[4-(benzyloxy)phenyl]acrylate;methyl(2E)-3-[4-(benzyloxy)phenyl]prop-2-enoate

Chemical Property of methyl (2E)-3-[4-(benzyloxy)phenyl]prop-2-enoate

Chemical Property:

• PSA: 35.53000
• LogP: 3.45180
• Solubility.: Dichloromethane
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 268.109944368
• Heavy Atom Count: 20
• Complexity: 310

Purity/Quality:

98% ^*data from raw suppliers

Methyl4-BenzyloxyCinnamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C=CC1=CC=C(C=C1)OCC2=CC=CC=C2
• Isomeric SMILES: COC(=O)/C=C/C1=CC=C(C=C1)OCC2=CC=CC=C2
• Uses: Methyl 4-Benzyloxy Cinnamate is cinnamic acid derivative used in structure-antifungal activity relationship study against Aspergillus flavus, Aspergillus terreus, and Aspergillus niger. An antifungal agent.

Technology Process of methyl (2E)-3-[4-(benzyloxy)phenyl]prop-2-enoate

There total 21 articles about methyl (2E)-3-[4-(benzyloxy)phenyl]prop-2-enoate 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%

methyl 4-hydroxycinnamate (3943-97-3) + benzyl bromide (100-39-0) → (E)-methyl 3-(4-(benzyloxy)phenyl)acrylate (84184-51-0)

Guidance literature:

With potassium carbonate; In acetone; at 23 ℃; for 4h; Reflux; Inert atmosphere;

DOI:10.1021/ja502744a

Reference yield: 100.0%

p-benzyloxybenzaldehyde (4397-53-9) + trimethyl phosphonoacetate (5927-18-4) → (E)-methyl 3-(4-(benzyloxy)phenyl)acrylate (84184-51-0)

Guidance literature:

trimethyl phosphonoacetate; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃;

p-benzyloxybenzaldehyde; In tetrahydrofuran; mineral oil; at 20 ℃;

Reference yield: 94.0%

p-benzyloxybenzaldehyde (4397-53-9) + trimethyl phosphonoacetate (5927-18-4) → Z-methyl 3-(4-benzyloxy)phenylacrylate (84184-51-0,73583-43-4)

Guidance literature:

trimethyl phosphonoacetate; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 1h; Inert atmosphere;

p-benzyloxybenzaldehyde; In tetrahydrofuran; at 0 ℃; Inert atmosphere;

DOI:10.1039/c003464a

upstream raw materials:

methanol

methyl 2-amino-3-(4-(benzyloxy) phenyl) propanoate

p-benzyloxybenzaldehyde

trimethyl phosphonoacetate

Downstream raw materials:

4-benzyloxycinnamyl alcohol

4-benzyloxycinnamic acid

2-(p-hydroxyphenylpropionoyloxy)(a)-4-(3',4'-dimethoxyphenyl)(e)-trans-quinolizidine

2-(p-methoxyphenylpropionoyloxy)(a)-4-(3',4'-dimethoxyphenyl)(e)-trans-quinolizidine

Refernces

• 1、 Deberardinis, Albert M.,Raccuia, Daniel S.,Thompson, Evrett N.,Maschinot, Chad A.,Hadden, M. Kyle. "Vitamin D3 analogues that contain modified A- and seco-B-rings as hedgehog pathway inhibitors". . p. 156 - 171. Retrieved 2015/02/19.
• 2、 -. "METHODS OF TREATMENT USING ARYLCYCLOPROPYLAMINE COMPOUNDS". Paragraph 0303-0304; 0309. . Retrieved 2014/12/09.