6302-93-8

Basic information

• Product Name: 5-[bis(phenylsulfanyl)methyl]benzo[1,3]dioxole
• Synonyms: 5-[bis(phenylsulfanyl)methyl]benzo[1,3]dioxole
• CAS NO: 6302-93-8
• Molecular Formula: C₂₀H₁₆O₂S₂
• Molecular Weight: 352.47
• Mol File: 6302-93-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 501.2°C at 760 mmHg
• Flash Point: 256.9°C
• Appearance: /
• Density: 1.33g/cm³
• Vapor Pressure: 1.11E-09mmHg at 25°C
• Refractive Index: 1.707
• CAS DataBase Reference: 5-[bis(phenylsulfanyl)methyl]benzo[1,3]dioxole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-[bis(phenylsulfanyl)methyl]benzo[1,3]dioxole(6302-93-8)
• EPA Substance Registry System: 5-[bis(phenylsulfanyl)methyl]benzo[1,3]dioxole(6302-93-8)

Safety Data

• Hazardous Substances Data: 6302-93-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H16O2S2/c1-3-7-16(8-4-1)23-20(24-17-9-5-2-6-10-17)15-11-12-18-19(13-15)22-14-21-18/h1-13,20H,14H2

Upstream product

• 103844-12-8 erythro-3-<3'',4''-dimethoxy-α,α-bis(phenylthio)benzyl>-2-(α-hydroxy-3',4'-methylenedioxybenzyl)-γ-butyrolactone 
• 495-76-1 piperonol 
• 108-98-5 thiophenol 
• 120-57-0 piperonal 
• 882-33-7 diphenyldisulfane 

Downstream Products

• 158665-03-3 (3R,4R,5R)-4-<1,3-Benzodioxol-5-ylbis(phenylthio)methyl>-3-<(4-(benzyloxy)-3-methoxyphenyl)methyl>-5-(l-menthyloxy)dihydro-2(3H)-furanone 
• 220597-13-7 Acetic acid (2R,3R)-3-(benzo[1,3]dioxol-5-yl-bis-phenylsulfanyl-methyl)-5-oxo-tetrahydro-furan-2-yl ester 
• 120-57-0 piperonal 
• 129819-59-6 N-2-(2-furylethyl) α-phenylthio-1,3-benzodioxole-5-ethanamine 
• 129819-55-2 N-3,5-hexadienyl α-phenylthio-1,3-benzodioxole-5-ethanamine 
• 129819-62-1 (2-Benzo[1,3]dioxol-5-yl-2-phenylsulfanyl-ethyl)-(2-furan-2-yl-ethyl)-carbamic acid ethyl ester 
• 129819-56-3 (2-Benzo[1,3]dioxol-5-yl-2-phenylsulfanyl-ethyl)-((E)-hexa-3,5-dienyl)-carbamic acid ethyl ester 
• 129819-57-4 ethyl <2-(1,3-benzodioxol-5-yl)-2-phenylthioethyl>methylcarbamate 
• 129819-51-8 ethyl 2-(1,3-benzodioxol-5-yl)-2-phenylthioethylcarbamate 
• 129819-53-0 methyl 2-(benzo[d][1,3]dioxol-5-yl)-2-(phenylthio)acetate 
• 126798-87-6 α-phenylthio-1,3-benzodioxoleacetaldehyde 
• 129819-50-7 α-phenylthio-1,3-benzodioxole-5-ethanamine 
• 81410-45-9 (8R,8'R-)8,8'-bis-(3'4'-methylenedioxybenzyl)-tetrahydrofuran (-)-dehydroxycubebin 
• 18423-69-3 (-)-Cubebin 

Relevant articles and documents

Dithioacetalization or thioetherification of benzyl alcohols using 9-mesityl-10-methylacridinium perchlorate photocatalyst

We report herein the use of 9-mesityl-10-methylacridinium perchlorate as the visible-light photocatalyst for dithioacetalization or thioetherification of benzyl alcohols in one pot using aerial dioxygen as a terminal oxidant. EPR analysis and Stern-Volmer

Enantioselective synthesis of natural dibenzylbutyrolactone lignans (-)-enterolactone, (-)-hinokinin, (-)-pluviatolide, (-)-enterodiol, and furofuran lignan (-)-eudesmin via tandem conjugate addition to γ-alkoxybutenolides1,2

A general and efficient method is described for the asymmetric synthesis of a variety of liguans. 5-(Menthyloxy)-2(5H)-furanones 5 proved to be excellent chiral synthons in this respect and could be transformed with complete stereoselectivity into a number of lignans. The addition of lithiated dithianes 7 to enantiomerically pure butenolides 5 was followed by quenching of the resulting lactone enolate anions with a benzylbromide (9) or with an aldehyde (6). This tandem addition quenching procedure gave the diastereomerically pure adducts 11, 26, or 27 in 50-67% yield, with a carbon skeleton as found in most natural lignans. As examples of the wide applicability of this method, the syntheses of the enantiomerically pure natural lignans (-)-hinokinin (23b), (-)-enterolactone (24a), (-)-pluviatolide (24c), and (-)-enterodiol (25) in overall yields of 29-37% from 5a and (-)eudesmin (30) in 16% overall yield from 5b are described.

General Conjugate-Addition Method for the Synthesis of Enantiomerically Pure Lignans. Total Synthesis of (-)- and (+)-Burseran, (-)-Dehydroxycubebin, (-)-Trichostin, (-)-Cubebin, (-)-5''-Methoxyhinokinin, and (-)-Hinokinin

Conjugate addition of benzylic diphenyldithioacetal anions to enantiomerically pure (-)-(2R)-and (+)-(2S)-(benzyloxy)-2,5-dihydro-4-furan (2 r and 2 s) gave complete lignan skeletons of the dibenzylbutane class.Desulfurization followed by hydrogenolysis and, when appropriate, oxidation gave the title enantiomerically pure > 99 percent ee) lignans 45 - 50 in 24 - 35 percent overall yields from 2 r and 2 s.