3-(1,3-Benzodioxole-5-ylmethylene)-4-(1,3-benzodioxole-5-ylmethyl)-3,4-dihydro-2(5H)-furanone

Base Information

• Chemical Name: 3-(1,3-Benzodioxole-5-ylmethylene)-4-(1,3-benzodioxole-5-ylmethyl)-3,4-dihydro-2(5H)-furanone
• CAS No.: 493-95-8
• Molecular Formula: C20H16O6
• Molecular Weight: 352.343
• DSSTox Substance ID: DTXSID201019951
• Nikkaji Number: J2.039.810H
• Mol file: 493-95-8.mol

Synonyms:AI3-26464;DTXSID201019951;3-(1,3-Benzodioxole-5-ylmethylene)-4-(1,3-benzodioxole-5-ylmethyl)-3,4-dihydro-2(5H)-furanone;NSC 150442

Chemical Property of 3-(1,3-Benzodioxole-5-ylmethylene)-4-(1,3-benzodioxole-5-ylmethyl)-3,4-dihydro-2(5H)-furanone

Chemical Property:

• Vapor Pressure: 3.7E-13mmHg at 25°C
• Melting Point: 146.4-148.4 °C(Solv: benzene (71-43-2))
• Boiling Point: 573.5°C at 760 mmHg
• Flash Point: 254.5°C
• PSA: 63.22000
• Density: 1.439g/cm³
• LogP: 2.94310
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 352.09468823
• Heavy Atom Count: 26
• Complexity: 575

Purity/Quality:

99%, ^*data from raw suppliers

Savinin 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(C(=CC2=CC3=C(C=C2)OCO3)C(=O)O1)CC4=CC5=C(C=C4)OCO5
• Isomeric SMILES: C1C(/C(=C/C2=CC3=C(C=C2)OCO3)/C(=O)O1)CC4=CC5=C(C=C4)OCO5
• Uses: Hibalactone is a plant terpenoid and lignoid which possess potent antiviral activities against severe acute respiratory syndrome Coronavirus.

Technology Process of 3-(1,3-Benzodioxole-5-ylmethylene)-4-(1,3-benzodioxole-5-ylmethyl)-3,4-dihydro-2(5H)-furanone

There total 12 articles about 3-(1,3-Benzodioxole-5-ylmethylene)-4-(1,3-benzodioxole-5-ylmethyl)-3,4-dihydro-2(5H)-furanone 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: 82.0%

(-)-isohibalactone (22554-63-8) → savinin (493-95-8)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 1h; Heating;

Reference yield: 63.0%

trans-4-(3,4-methylenedioxybenzyl)-3-(α-methylsulfonyloxy-3,4-methylenedioxybenzyl)dihydrofuran-2(3H)-one → (-)-isohibalactone (22554-63-8) + savinin (493-95-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 5h; Ambient temperature;

Reference yield:

Acetic acid benzo[1,3]dioxol-5-yl-((R)-4-benzo[1,3]dioxol-5-ylmethyl-2-oxo-tetrahydro-furan-3-yl)-methyl ester → savinin (493-95-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 80 ℃; for 1.5h; Yield given;

DOI:10.1139/v97-127

upstream raw materials:

(-)-isohibalactone

3-(1,3 benzodioxol-5-yl)propionic acid

(R)-(+)-3-piperonyl-4-butanolide

(4S)-4-isopropyl-3-[3-(3,4-methylenedioxyphenyl)propanoyl]-2-oxazolidinone

Downstream raw materials:

(+)-Isohinokinin

(-)-hinokinin

Refernces

• 1、 Honda, Toshio,Kimura, Nobuaki,Sato, Shigeki,Kato, Daishiro,Tominaga, Hideo. "Chiral Synthesis of Lignan Lactones, (-)-Hinokinin, (-)-Deoxypodorhizone, (-)-Isohibalactone and (-)-Savinin by Means of Enantioselective Deprotonation". . p. 1043 - 1046. Retrieved 2007/10/02.