Genkdaphine

Base Information

• Chemical Name: Genkdaphine
• CAS No.: 139402-21-4
• Molecular Formula: C₂₀H₁₆O₇
• Molecular Weight: 368.343
• DSSTox Substance ID: DTXSID10161035
• Wikidata: Q83029397
• Mol file: 139402-21-4.mol

Synonyms:4-oxo-2,6-bis(3',4'-methylenedioxyphenyl)-3,7-dioxabicyclo(3.3.0)octane;4-oxosesamin;genkdaphine

Chemical Property of Genkdaphine

Chemical Property:

• Vapor Pressure: 1.1E-12mmHg at 25°C
• Melting Point: 140 - 141 °C (hexane)
• Boiling Point: 562.6°Cat760mmHg
• Flash Point: 249.7°C
• PSA: 72.45000
• Density: 1.46g/cm³
• LogP: 2.74580
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 368.08960285
• Heavy Atom Count: 27
• Complexity: 597

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(C(O1)C3=CC4=C(C=C3)OCO4)C(=O)OC2C5=C6C(=CC=C5)OCO6
• Isomeric SMILES: C1[C@@H]2[C@H]([C@@H](O1)C3=CC4=C(C=C3)OCO4)C(=O)O[C@H]2C5=C6C(=CC=C5)OCO6

Technology Process of Genkdaphine

There total 38 articles about Genkdaphine 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: 84.0%

(1R,2S,5S,6S)-4-hydroxy-2,6-bis(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (58262-61-6,61254-18-0,63427-86-1) → (+)-aptosimon (105661-99-2,105662-90-6,139402-21-4,61254-17-9)

Guidance literature:

With 4 A molecular sieve; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1271/bbb.67.838

Reference yield: 70.0%

rac-(4R,5S)-5-(3,4-methylenedioxyphenyl)-3-diazo-4-[[(3,4-methylenedioxybenzyl)oxy]methyl]tetrahydro-2-furanone → rac-(1S,2R,5R,6S)-2,6-bis(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octan-8-one (61254-17-9,105661-99-2,105662-90-6,139402-21-4)

Guidance literature:

dirhodium tetraacetate; In dichloromethane; Ambient temperature;

DOI:10.1039/a805296d

Reference yield: 28.0%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + (4S,5R)-5-Benzo[1,3]dioxol-5-yl-4-(benzo[1,3]dioxol-5-yl-methoxy-methoxymethyl)-dihydro-furan-2-one (105602-56-0,139714-60-6,139714-61-7) → (+/-)-aptosimon (61254-17-9,105661-99-2,105662-90-6,139402-21-4) + rac-(1S,2R,5R,6S)-2,6-bis(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octan-8-one (61254-17-9,105661-99-2,105662-90-6,139402-21-4)

Guidance literature:

With triethylamine; In tetrahydrofuran; diethyl ether; at 0 ℃; for 3h;

upstream raw materials:

(1R,2S,5S,6S)-4-hydroxy-2,6-bis(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane

piperonal

(3R)-3-[(R)-(3,4-methylenedioxyphenyl)(triisopropylsilyloxy)methyl]-4-butanolide

(3R)-3-[(S)-(3,4-methylenedioxyphenyl)(triisopropylsilyloxy)methyl]-4-butanolide

Downstream raw materials:

rac-(1R,2R,5R,6S)-2,6-bis(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane

Refernces

• 1、 Brown,Bataille,Bruton,Hinks,Swain. "C-H insertion approach to the synthesis of endo,exo-furofuranones: Synthesis of (±)-asarinin, (±)-epimagnolin A, and (±)-fargesin". . p. 6719 - 6728. Retrieved 2007/10/03.
• 2、 Stevens, David R.,Till, Clive P.,Whiting, Donald A.. "A New Synthetic Route to Furofuranoid Lignans via Intramolecular Mukaiyama reaction". . p. 185 - 190. Retrieved 2007/10/02.