7-bromo-3,3a,6,8b-tetramethyl-2,3-dihydro-1H-cyclopenta[b]benzofuran

Base Information

• Chemical Name: 7-bromo-3,3a,6,8b-tetramethyl-2,3-dihydro-1H-cyclopenta[b]benzofuran
• CAS No.: 6790-63-2
• Molecular Formula: C15H19BrO
• Molecular Weight: 295.219
• NSC Number: 305227
• DSSTox Substance ID: DTXSID20987263
• Wikidata: Q104921789
• ChEMBL ID: CHEMBL1971985
• Mol file: 6790-63-2.mol

Synonyms:NSC305227;6790-63-2;NSC-305227;CHEMBL1971985;DTXSID20987263;NCI60_002577;7-bromo-3,3a,6,8b-tetramethyl-2,3-dihydro-1H-cyclopenta[b]benzofuran;11-bromo-2,5,6,10-tetramethyl-7-oxatricyclo[6.4.0.0?,?]dodeca-1(12),8,10-triene;7-bromo-3,3a,6,8b-tetramethyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan;(3S)-7-Bromo-2,3,3a,8b-tetrahydro-3,3abeta,6,8bbeta-tetramethyl-1H-cyclopenta[b]benzofuran

Chemical Property of 7-bromo-3,3a,6,8b-tetramethyl-2,3-dihydro-1H-cyclopenta[b]benzofuran

Chemical Property:

• Vapor Pressure: 0.000239mmHg at 25°C
• Boiling Point: 335.1°Cat760mmHg
• Flash Point: 131.7°C
• PSA: 9.23000
• Density: 1.307g/cm³
• LogP: 4.59620
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 294.06193
• Heavy Atom Count: 17
• Complexity: 331

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(C1(OC3=C2C=C(C(=C3)C)Br)C)C

Technology Process of 7-bromo-3,3a,6,8b-tetramethyl-2,3-dihydro-1H-cyclopenta[b]benzofuran

There total 38 articles about 7-bromo-3,3a,6,8b-tetramethyl-2,3-dihydro-1H-cyclopenta[b]benzofuran 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: 87.0%

(-)-Debromoaplysin (23444-68-0) → (-)-Aplysin (6790-63-2)

Guidance literature:

With N-Bromosuccinimide; In tetrachloromethane; Heating;

DOI:10.1016/S0040-4039(00)74123-2

Reference yield:

laurinterol (10539-87-4) → (-)-Aplysin (6790-63-2)

Guidance literature:

With hydrogen bromide; In diethyl ether; at 20 ℃; for 0.25h;

DOI:10.3390/md16110443

Reference yield:

(3aS,8bS)-(-)-3a,8b-Dihydro-3,3a,6,8b-tetramethyl-1H-cyclopentabenzofuran (73307-78-5) → (-)-Aplysin (6790-63-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / H₂ / PtO₂ / ethanol / 3 h / Ambient temperature

2: 84 percent / NaHCO₃, Br₂ / CHCl₃ / 0.17 h / Ambient temperature

With hydrogen; bromine; sodium hydrogencarbonate; platinum(IV) oxide; In ethanol; chloroform;

DOI:10.1021/jo00080a014

upstream raw materials:

(-)-Debromoaplysin

(3aS,8bS)-(-)-3a,8b-Dihydro-3,3a,6,8b-tetramethyl-1H-cyclopentabenzofuran

(3S,3aR,8bS)-(-)-2,3,3a,8b-Tetrahydro-3-hydroxy-3,3a,6,8b-tetramethyl-1H-cyclopentabenzofuran

(1S,3R)-3-(2-hydroxy-4-methylphenyl)-1,3-dimethyl-2-methylidenecyclopentanol

Refernces

• 1、 Fletcher, Catherine J.,Blair, Daniel J.,Wheelhouse, Katherine M.P.,Aggarwal, Varinder K.. "The total synthesis of (-)-aplysin via a lithiation-borylation- propenylation sequence". experimental part. p. 7598 - 7604. Retrieved 2012/09/21.
• 2、 Takano, Seiichi,Moriya, Minoru,Ogasawara, Kunio. "ENANTIOCONTROLLED SYNTHESES OF THE CUPARENE SESQUITERPENES, (-)-HERBERTENE, (+)-β-CUPARENONE, (-)-DEBROMOAPLYSIN, AND (-)-APLYSIN". . p. 329 - 332. Retrieved 2007/10/02.