6-(4-Methoxybenzylidene)-1,3-benzodioxol-5(6H)-one

Base Information

• Chemical Name: 6-(4-Methoxybenzylidene)-1,3-benzodioxol-5(6H)-one
• CAS No.: 63194-80-9
• Molecular Formula: C15H12O4
• Molecular Weight: 256.258
• NSC Number: 269129
• UNII: 8MC2RW2ZB7
• Nikkaji Number: J325.180B,J302.682E
• Mol file: 63194-80-9.mol

Synonyms:OBTUSAQUINONE DERIV JURD 2351;63194-80-9;6-(4-Methoxybenzylidene)-1,3-benzodioxol-5(6H)-one;NSC 269129;NSC269129;NSC-269129;8MC2RW2ZB7;6-(4-Methoxybenzylidene)-1,3-benzodioxole-5(6H)-one;(6E)-6-[(4-methoxyphenyl)-methylene]-1,3-benzodioxol-5-one;(6E)-6-[(4-methoxyphenyl)methylene]-1,3-benzodioxol-5-one;1,3-Benzodioxol-5(6H)-one, 6-[(4-methoxyphenyl)methylene]-;(6E)-6-[(4-Methoxyphenyl)methylene]-1,3-benzodioxol-5(6H)-one;1,3-Benzodioxol-5(6H)-one, 6-[(4-methoxyphenyl)methylene]-, (6E)-;3,4-Methylenedioxy-6-(4-methoxyphenylmethylidene)cyclohexan-2,4-dien-1-one;6-[(E)-4-Methoxybenzylidene]-3,4-methylenedioxy-2,4-cyclohexadien-1-one

Chemical Property of 6-(4-Methoxybenzylidene)-1,3-benzodioxol-5(6H)-one

Chemical Property:

• Vapor Pressure: 3.78E-09mmHg at 25°C
• Boiling Point: 473.9°C at 760 mmHg
• Flash Point: 214.4°C
• Density: 1.31g/cm³
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 256.07355886
• Heavy Atom Count: 19
• Complexity: 465

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C=C2C=C3C(=CC2=O)OCO3
• Isomeric SMILES: COC1=CC=C(C=C1)/C=C/2\C=C3C(=CC2=O)OCO3

Technology Process of 6-(4-Methoxybenzylidene)-1,3-benzodioxol-5(6H)-one

There total 9 articles about 6-(4-Methoxybenzylidene)-1,3-benzodioxol-5(6H)-one 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: 54.0%

2-(4-Methoxybenzyl)-4,5-(methylenedioxy)phenol (63194-78-5) → 3,4-dimethoxy-6-(4-methoxyphenylmethylidene)cyclohexa-2,4-dien-1-one (63194-80-9)

Guidance literature:

With silver(l) oxide; In tetrahydrofuran; at 40 ℃; for 3.5h;

DOI:10.1002/chem.201904903

Reference yield: 51.0%

C15H14O4 → 3,4-dimethoxy-6-(4-methoxyphenylmethylidene)cyclohexa-2,4-dien-1-one (63194-80-9)

Guidance literature:

With silver(l) oxide; In diethyl ether; for 2.5h; Reflux; Inert atmosphere;

DOI:10.1002/anie.201810760

Reference yield:

Sesamol (533-31-3) → 3,4-dimethoxy-6-(4-methoxyphenylmethylidene)cyclohexa-2,4-dien-1-one (63194-80-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: trifluoroacetic acid / 3 h / Reflux; Inert atmosphere

2.1: tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

3.1: toluene-4-sulfonic acid / dichloromethane / 0.08 h / 20 °C / Schlenk technique; Inert atmosphere

3.2: 1.5 h / Schlenk technique

4.1: C₂₃H₂₅F₆N₃O₂

With C₂₃H₂₅F₆N₃O₂; toluene-4-sulfonic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1.1: |Duff Aldehyde Synthesis;

DOI:10.1002/anie.201409894

upstream raw materials:

Sesamol

4,5-methylenedioxy-2-hydroxybenzaldehyde

4-methoxyphenyl magnesium bromide

6-(4-methoxybenzyl)benzo[d][1,3]dioxol-5-ol

Downstream raw materials:

(6R,7R,8S)-6-Ethoxy-8-(4-methoxy-phenyl)-7-methyl-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]chromene

2-(α-(2-hydroxy-3-t-butylphenyl)-p-methoxybenzylidene)-4,5-methylenedioxyphenol

(7S,8R)-8-(4-methoxyphenyl)-7-methyl-7,8-dihydro-[1,3]dioxolo[4,5-g]chromen-6-one

(7S,8R)-7-ethyl-8-(4-methoxyphenyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]chromen-6-one

Refernces

• 1、 Trost, Barry M.,Zuo, Zhijun. "Highly Regio-, Diastereo-, and Enantioselective Synthesis of Tetrahydroazepines and Benzo[b]oxepines through Palladium-Catalyzed [4+3] Cycloaddition Reactions". supporting information. p. 1243 - 1247. Retrieved 2019/11/25.
• 2、 Lam, Heather,Qureshi, Zafar,Wegmann, Marcus,Lautens, Mark. "Transition-Metal-Free [4+3]-Cycloaddition of ortho-Quinone Methides and Isomünchnones: Catalytic and Diastereoselective Assembly of Oxa-bridged Oxazocine Scaffolds". . p. 16185 - 16189. Retrieved 2018/11/23.