(3Ar,5aR,6aR,6bR)-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno[2,3-g][1,3]benzodioxole

Base Information

• Chemical Name: (3Ar,5aR,6aR,6bR)-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno[2,3-g][1,3]benzodioxole
• CAS No.: 145107-27-3
• Molecular Formula: C9H12 O3
• Molecular Weight: 168.192
• DSSTox Substance ID: DTXSID20447993
• Nikkaji Number: J623.071G
• Wikidata: Q82266903
• Mol file: 145107-27-3.mol

Synonyms:145107-27-3;(3Ar,5aR,6aR,6bR)-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno[2,3-g][1,3]benzodioxole;DTXSID20447993;GAUDXMCZQNKKEF-WCTZXXKLSA-N;AKOS006237605;J-008057;(3AR)-3A,5A,6A,6B-TETRAHYDRO-2,2-DI-METH;(3aR,5aR,6aR,6bR)-2,2-Dimethyl-3a,5a,6a,6b-tetrahydro-2H-oxireno[e][1,3]benzodioxole;2,2-Dimethyl-4alpha,5alpha-epoxy-3aalpha,4,5,7aalpha-tetrahydro-1,3-benzodioxole;[3aR-(3aalpha,5abeta,6abeta,6balpha)]-3a,5a,6a,6b-Tetrahydro-2,2-dimethyloxireno[e]-1,3-benzodioxole;[3aR-(3aalpha,5abeta,6abeta,6balpha)]-3a,5a,6a,6b-Tetrahydro-2,2-dimethyloxireno[e]-1,3-benzodioxole, 96%

Chemical Property of (3Ar,5aR,6aR,6bR)-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno[2,3-g][1,3]benzodioxole

Chemical Property:

• Vapor Pressure: 0.118mmHg at 25°C
• Refractive Index: 1.495
• Boiling Point: 227.2°Cat760mmHg
• Flash Point: 73.7°C
• PSA: 30.99000
• Density: 1.165g/cm³
• LogP: 0.84370
• Storage Temp.: ?20°C
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 168.078644241
• Heavy Atom Count: 12
• Complexity: 246

Purity/Quality:

98%min ^*data from raw suppliers

[3aR-(3aα,5aβ,6aβ,6bα)]-3a,5a,6a,6b-Tetrahydro-2,2-dimethyloxireno[e]-1,3-benzodioxole 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C=CC3C(C2O1)O3)C
• Isomeric SMILES: CC1(O[C@@H]2C=C[C@@H]3[C@H]([C@@H]2O1)O3)C

Technology Process of (3Ar,5aR,6aR,6bR)-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno[2,3-g][1,3]benzodioxole

There total 11 articles about (3Ar,5aR,6aR,6bR)-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno[2,3-g][1,3]benzodioxole 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: 94.0%

(3aR,4S,5aR,6aR,6bS)-2,2-dimethylhexahydrooxireno[2′,3′:3,4]-benzo[1,2-d][1,3]dioxol-4-ol (1583240-50-9) → (3aR,5aR,6aR,6bR)-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno-[2′,3′:3,4]benzo[1,2-d][1,3]dioxole (145107-27-3)

Guidance literature:

(3aR,4S,5aR,6aR,6bS)-2,2-dimethylhexahydrooxireno[2′,3′:3,4]-benzo[1,2-d][1,3]dioxol-4-ol; With methanesulfonyl chloride; triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 0.75h; Inert atmosphere;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; for 2h; enantioselective reaction; Inert atmosphere;

DOI:10.1021/jo402764v

Reference yield: 90.0%

cis-2,2-dimethyl-3a,7a-dihydrobenzo[1,3]dioxole (80409-75-2,343865-40-7) → (1α,2β,4β,7α)-3,8,10-trioxa-9,9-dimethyl-tricyclo<5,3,0,02,4>doc-5-ene (143308-52-5,145107-27-3)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 5h;

Reference yield: 88.0%

(1S,2S,5R,6R)-3-bromo-5,6-epoxy-1,2-O-isopropylidencyclohex-3-en-1,2-diol (130669-74-8) → (3aR,5aR,6aR,6bR)-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno-[2′,3′:3,4]benzo[1,2-d][1,3]dioxole (145107-27-3)

Guidance literature:

With tri-n-butyl-tin hydride; 1,1'-azobis(1-cyanocyclohexanenitrile); In tetrahydrofuran; Inert atmosphere; Reflux;

DOI:10.1016/j.tetasy.2009.08.011

upstream raw materials:

(1S,2S,5R,6R)-3-bromo-5,6-epoxy-1,2-O-isopropylidencyclohex-3-en-1,2-diol

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene

(3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole

(1R,2R,3S,4S)-1-chloro-2-acetoxy-3,4-(isopropylidenedioxy)-cyclohex-5-ene

Downstream raw materials:

(3S,4S,5S)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid

(1S,2S,5R,6S)-2-phenylselenyl-5,6-isopropylidenedioxycyclohex-3-en-1-ol

(+/-)-9-<(1'S,2'S,3'S,4'S)-2',3',4'-trihydroxycyclohexanyl>adenine

(+/-)-9-<(1'R,2'S,3'S,4'S)-2',3',4'-trihydroxycyclohexanyl>adenine

Refernces

• 1、 Giro Mannas, Carles,Paddock, Victoria L.,Bochet, Christian G.,Spivey, Alan C.,White, Andrew J. P.,Mann, Inderjit,Oppolzer, Wolfgang. "Total synthesis of the lycorenine-type amaryllidaceae alkaloid (±)-Clivonine via a biomimetic ring-switch from a lycorine-type progenitor". supporting information; experimental part. p. 5176 - 5178. Retrieved 2010/06/18.
• 2、 Bellomo, Ana,Camarano, Soledad,Rossini, Carmen,Gonzalez, David. "Enantiospecific synthesis and insect feeding activity of sulfur-containing cyclitols". scheme or table. p. 44 - 51. Retrieved 2011/03/20.