Retrochinensin

Base Information

• Chemical Name: Retrochinensin
• CAS No.: 5707-96-0
• Molecular Formula: C21H16O6
• Molecular Weight: 364.354
• NSC Number: 254665
• UNII: FPB7483LCY
• DSSTox Substance ID: DTXSID80972539
• Nikkaji Number: J1.330.728H
• Wikidata: Q82956320
• ChEMBL ID: CHEMBL440125
• Mol file: 5707-96-0.mol

Synonyms:Retrochinensin;5707-96-0;NSC254665;FPB7483LCY;CHEMBL440125;NSC-254665;9-(3,4-Dimethoxy-phenyl)-8-H-furo(3',4':6,7)naphtho(2,3-d)(1,3)dioxol-6-one;NSC 254665;9-(3,4-Dimethoxy-phenyl)-8-H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one;UNII-FPB7483LCY;DTXSID80972539;BDBM50280960;NCI60_002042;5-(3,4-dimethoxyphenyl)-6H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one;9-(3,4-Dimethoxy-phenyl)-8H-furo[3'',4'':6,7]naphtho[2,3-d][1,3]dioxol-6-one;9-(3,4-Dimethoxyphenyl)-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one;9-(3,4-DIMETHOXYPHENYL)FURO(3',4':6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-6(8H)-ONE;FURO(3',4':6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-6(8H)-ONE, 9-(3,4-DIMETHOXYPHENYL)-;NAPHTHO(2,3-D)-1,3-DIOXOLE-6-CARBOXYLIC ACID, 8-(3,4-DIMETHOXYPHENYL)-7-(HYDROXYMETHYL)-, .GAMMA.-LACTONE

Chemical Property of Retrochinensin

Chemical Property:

• Boiling Point: 593.2°Cat760mmHg
• Flash Point: 262.2°C
• PSA: 63.22000
• Density: 1.376g/cm³
• LogP: 3.92310
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 364.09468823
• Heavy Atom Count: 27
• Complexity: 567

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C2=C3C=C4C(=CC3=CC5=C2COC5=O)OCO4)OC

Technology Process of Retrochinensin

There total 28 articles about Retrochinensin 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%

4-(3',4'-dimethoxyphenyl)-3-hydroxymethyl-6,7-methylenedioxy-3,4-dihydro-2-naphthoic acid γ-lactone (103844-18-4,118626-89-4) → retrochinensin (5707-96-0)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In chloroform; benzene; for 48h; Heating;

Reference yield: 94.0%

2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-dimethoxyphenyl)-naphthalene (42923-60-4) → retrochinensin (5707-96-0)

Guidance literature:

With 1-Phenylbut-1-en-3-one; dihydridotetrakis(triphenylphosphine)ruthenium; In toluene; for 10h; Heating;

DOI:10.1016/S0040-4039(00)84020-4

Reference yield: 72.0%

6,7-methylenedioxy-1-(3,4-dimethoxyphenyl)naphthalene-2,3-dicarboxylic acid 2-ethyl ester (289622-32-8) → retrochinensin (5707-96-0)

Guidance literature:

With lithium borohydride; sodium hydride; In tetrahydrofuran; 1,4-dioxane; for 28h; Heating;

DOI:10.1016/S0040-4020(02)00616-6

upstream raw materials:

2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-dimethoxyphenyl)-naphthalene

1-(3',4'-dimethoxyphenyl)-6,7-methylenedioxynaphthalene-2,3-dicarboxylic anhydride

4-(3',4'-dimethoxyphenyl)-3-hydroxymethyl-6,7-methylenedioxy-3,4-dihydro-2-naphthoic acid γ-lactone

erythro-3-<3'',4''-dimethoxy-α,α-bis(phenylthio)benzyl>-2-(α-hydroxy-3',4'-methylenedioxybenzyl)-γ-butyrolactone

Downstream raw materials:

2,3-bis-(hydroxymethyl)-6,7-methylenedioxy-1-(3',4'-dimethoxyphenyl)-naphthalene

Refernces

• 1、 Ge, Xiang,Jiang, Haowen,Li, Jinlong. "Rapid continuous photoflow synthesis of naturally occurring arylnaphthalene lignans and their analogs". . . Retrieved 2021/05/10.
• 2、 Flanagan, Stuart R,Harrowven, David C,Bradley, Mark. "A new benzannulation reaction and its application in the multiple parallel synthesis of arylnaphthalene lignans". . p. 5989 - 6001. Retrieved 2007/10/03.