3-Benzo[1,3]dioxol-5-yl-5-hydroxy-5-(4-methoxy-phenyl)-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one

Base Information

• Chemical Name: 3-Benzo[1,3]dioxol-5-yl-5-hydroxy-5-(4-methoxy-phenyl)-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one
• CAS No.: 162256-50-0
• Molecular Formula: C28H26 O9
• Molecular Weight: 506.509
• DSSTox Substance ID: DTXSID30432113
• Pharos Ligand ID: Z37J5GRNGL84
• ChEMBL ID: CHEMBL8981
• Mol file: 162256-50-0.mol

Synonyms:CI 1020;PD 156707;PD-156707

Chemical Property of 3-Benzo[1,3]dioxol-5-yl-5-hydroxy-5-(4-methoxy-phenyl)-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.623
• Boiling Point: 722.338°C at 760 mmHg
• Flash Point: 242.505°C
• PSA: 101.91000
• Density: 1.351g/cm³
• LogP: 3.84810
• Storage Temp.: Store at +4°C
• XLogP3: 4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 8
• Exact Mass: 506.15768240
• Heavy Atom Count: 37
• Complexity: 824

Purity/Quality:

97% ^*data from raw suppliers

CI1020 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C2(C(=C(C(=O)O2)C3=CC4=C(C=C3)OCO4)CC5=CC(=C(C(=C5)OC)OC)OC)O
• Uses: A novel endothelin-A receptor antagonist, in hypoxic pulmonary hypertension.

Technology Process of 3-Benzo[1,3]dioxol-5-yl-5-hydroxy-5-(4-methoxy-phenyl)-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one

There total 5 articles about 3-Benzo[1,3]dioxol-5-yl-5-hydroxy-5-(4-methoxy-phenyl)-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-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:

→ 2-buten-4-olide (497-23-4) + 3-Benzo[1,3]dioxol-5-yl-5-hydroxy-5-(4-methoxy-phenyl)-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one (162256-50-0)

Guidance literature:

Reference yield:

(E)-1-(4-methoxyphenyl)-3-(3,4-methylenedioxyphenyl)prop-2-en-1-one (144309-50-2) → 3-Benzo[1,3]dioxol-5-yl-5-hydroxy-5-(4-methoxy-phenyl)-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one (162256-50-0)

Guidance literature:

Multi-step reaction with 3 steps

1: HOAc / 2-ethoxy-ethanol / 100 °C

2: p-TsOH / Heating

3: 1.) NaOMe, 2.) AcOH / 1.) MeOH, 60 deg C, 24 h, 2.) MeOH, reflux, 24 h

With sodium methylate; toluene-4-sulfonic acid; acetic acid; In 2-ethoxy-ethanol;

DOI:10.1021/jm980504w

Reference yield:

piperonal (120-57-0,30024-74-9) → 3-Benzo[1,3]dioxol-5-yl-5-hydroxy-5-(4-methoxy-phenyl)-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one (162256-50-0)

Guidance literature:

Multi-step reaction with 4 steps

1: NaOH / ethanol

2: HOAc / 2-ethoxy-ethanol / 100 °C

3: p-TsOH / Heating

4: 1.) NaOMe, 2.) AcOH / 1.) MeOH, 60 deg C, 24 h, 2.) MeOH, reflux, 24 h

With sodium hydroxide; sodium methylate; toluene-4-sulfonic acid; acetic acid; In 2-ethoxy-ethanol; ethanol;

DOI:10.1021/jm980504w

upstream raw materials:

3,4,5-trimethoxy-benzaldehyde

2-benzo<1,3>dioxol-5-yl-4-(4-methoxyphenyl)-4-oxobutyric acid methyl ester

piperonal

(E)-1-(4-methoxyphenyl)-3-(3,4-methylenedioxyphenyl)prop-2-en-1-one

Refernces

• 1、 Patt, William C.,Edmunds, Jeremy J.,Repine, Joseph T.,Berryman, Kent A.,Reisdorph, Billy R.,Lee, Chet,Plummer, Mark S.,Shahripour, Aurash,Haleen, Stephen J.,Keiser, Joan A.,Flynn, Mike A.,Welch, Kathleen M.,Reynolds, Elwood E.,Rubin, Ron,Tobias, Brian,Hallak, Hussein,Doherty, Annette M.. "Structure-activity relationships in a series of orally active γ- hydroxy butenolide endothelin antagonists". . p. 1063 - 1074. Retrieved 2007/10/03.
• 2、 Doherty,Patt,Edmunds,Berryman,Reisdorph,Plummer,Shahripour,Lee,Cheng,Walker,Haleen,Keiser,Flynn,Welch,Hallak,Taylor,Reynolds. "Discovery of a novel series of orally active non-peptide endothelin-A (ET(A)) receptor-selective antagonists". . p. 1259 - 1263. Retrieved 2007/10/02.