3,4-Methylenedioxy-4'-phenylchalcone

Base Information

• Chemical Name: 3,4-Methylenedioxy-4'-phenylchalcone
• CAS No.: 42580-60-9
• Molecular Formula: C22H16O3
• Molecular Weight: 328.367
• European Community (EC) Number: 653-931-5
• Nikkaji Number: J3.073.298G
• Wikidata: Q76313791
• Mol file: 42580-60-9.mol

Synonyms:42580-60-9;3,4-METHYLENEDIOXY-4'-PHENYLCHALCONE;(2E)-3-(2H-1,3-benzodioxol-5-yl)-1-{[1,1'-biphenyl]-4-yl}prop-2-en-1-one;(E)-3-(1,3-benzodioxol-5-yl)-1-(4-phenylphenyl)prop-2-en-1-one;MFCD00022996;AKOS003603902;1-(Biphenyl-4-yl)-3-(1,3-benzodioxole-5-yl)-2-propene-1-one;(2E)-3-(2H-1,3-Benzodioxol-5-yl)-1-(4-phenylphenyl)prop-2-en-1-one

Chemical Property of 3,4-Methylenedioxy-4'-phenylchalcone

Chemical Property:

• XLogP3: 5.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 328.109944368
• Heavy Atom Count: 25
• Complexity: 472

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1OC2=C(O1)C=C(C=C2)C=CC(=O)C3=CC=C(C=C3)C4=CC=CC=C4
• Isomeric SMILES: C1OC2=C(O1)C=C(C=C2)/C=C/C(=O)C3=CC=C(C=C3)C4=CC=CC=C4

Technology Process of 3,4-Methylenedioxy-4'-phenylchalcone

There total 5 articles about 3,4-Methylenedioxy-4'-phenylchalcone 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: 92.0%

(E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(4-bromophenyl)prop-2-en-1-one (36716-01-5) + phenylboronic acid (98-80-6) → (E)-1-([1,1'-biphenyl]-4-yl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one (42580-60-9)

Guidance literature:

With potassium fluoride; palladium diacetate; In PEG-400; ethanol; at 110 ℃; for 0.5h; Microwave irradiation;

DOI:10.1016/j.tetlet.2012.03.079

Reference yield: 85.0%

biphenyl-4-acetaldehyde (92-91-1) + piperonal (120-57-0,30024-74-9) → (E)-1-([1,1'-biphenyl]-4-yl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one (42580-60-9)

Guidance literature:

biphenyl-4-acetaldehyde; With sodium hydroxide; In ethanol; for 0.333333h; Cooling with ice;

piperonal; In ethanol; at 20 ℃;

DOI:10.1590/S0103-50532013000100018

Reference yield: 66.0%

piperonal (120-57-0,30024-74-9) + para-bromoacetophenone (99-90-1) + phenylboronic acid (98-80-6) → (E)-1-([1,1'-biphenyl]-4-yl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one (42580-60-9)

Guidance literature:

With potassium carbonate; In toluene; at 100 ℃; for 12h; Catalytic behavior; Inert atmosphere;

DOI:10.1039/c6nj02402e

upstream raw materials:

biphenyl-4-acetaldehyde

piperonal

para-bromoacetophenone

(E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(4-bromophenyl)prop-2-en-1-one

Downstream raw materials:

4-Benzo[1,3]dioxol-5-yl-2-biphenyl-4-yl-6-phenyl-pyridine

5-Benzo[1,3]dioxol-5-yl-3-biphenyl-4-yl-isoxazole

4-Benzo[1,3]dioxol-5-yl-2,6-bis-biphenyl-4-yl-pyridine

4-benzo[1,3]dioxol-5-yl-2-biphenyl-4-yl-6-(4-chloro-phenyl)-pyridine

Refernces

• 1、 Patel, Heta A.,Patel, Arun L.,Bedekar, Ashutosh V.. "Polyaniline coated on celite, a heterogeneous support for palladium: Applications in catalytic Suzuki and one-pot Suzuki-aldol reactions". . p. 8935 - 8945. Retrieved 2016/10/13.