(+/-)-2-ACETYL-9-AZA BICYCLO[4.2.1]NON-2-ENE FUMARATE

Base Information

• Chemical Name: (+/-)-2-ACETYL-9-AZA BICYCLO[4.2.1]NON-2-ENE FUMARATE
• CAS No.: 64285-06-9
• Molecular Formula: C10H15 N O
• Molecular Weight: 165.235
• Hs Code.: 2933990090
• European Community (EC) Number: 689-000-5
• UNII: 80023A73NK
• DSSTox Substance ID: DTXSID50867064
• Nikkaji Number: J18.582E
• Wikipedia: Anatoxin-a
• Wikidata: Q104246548
• Pharos Ligand ID: 5FZVDKY71PAA
• ChEMBL ID: CHEMBL2332144
• Mol file: 64285-06-9.mol

Synonyms:Ethanone,1-(9-azabicyclo[4.2.1]non-2-en-2-yl)-, (1R)-; 9-Azabicyclo[4.2.1]nonane,ethanone deriv.; (+)-Anatoxin a; (+)-Anatoxin a; (+)-Anatoxin-a; Anatoxin I; Anatoxin a; Anatoxin a

Chemical Property of (+/-)-2-ACETYL-9-AZA BICYCLO[4.2.1]NON-2-ENE FUMARATE

Chemical Property:

• Appearance/Colour: Lyophilized Solid
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Boiling Point: 291 °C at 760 mmHg
• PKA: 9.4(at 25℃)
• Flash Point: 124.7 °C
• PSA: 29.10000
• Density: 1.037 g/cm³
• LogP: 1.74500
• Storage Temp.: Desiccate at +4°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 165.115364102
• Heavy Atom Count: 12
• Complexity: 232

Purity/Quality:

99% ^*data from raw suppliers

(+/-)-ANATOXIN A 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Anatoxin-a
• Canonical SMILES: CC(=O)C1=CCCC2CCC1N2
• Isomeric SMILES: CC(=O)C1=CCC[C@@H]2CC[C@H]1N2
• Uses: (+)-Anatoxin-a is a secondary, bicyclic amine alkaloid and cyanotoxin with acute neurotoxicity. The toxin is produced by at least four different genera of cyanobacteria and has been reported in North America, Europe, Africa, Asia, and New Zealand. Symptoms of anatoxin exposure are loss of coordination, muscular fasciculations, convulsions and death by respiratory paralysis.

Technology Process of (+/-)-2-ACETYL-9-AZA BICYCLO[4.2.1]NON-2-ENE FUMARATE

There total 66 articles about (+/-)-2-ACETYL-9-AZA BICYCLO[4.2.1]NON-2-ENE FUMARATE 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: 99.0%

(+)-(1R)-2-acetyl-9-benzyloxycarbonyl-9-azabicyclo[4.2.1]-2-nonene (120692-41-3) → anatoxin-a (64285-06-9)

Guidance literature:

With trimethylsilyl iodide; In acetonitrile; at -10 ℃; for 0.333333h;

DOI:10.1016/j.tet.2004.06.021

Reference yield: 76.0%

(-)-N-tosylanatoxin-a (143264-77-1) → anatoxin-a (64285-06-9)

Guidance literature:

With disodium hydrogenphosphate; sodium amalgam; In methanol; at -40 ℃; for 0.166667h;

DOI:10.1016/0040-4039(92)80026-G

Reference yield:

(-)-(5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosylpyrrolidin-2-one (132974-84-6) → anatoxin-a (64285-06-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 92 percent / DIBAL / CH₂Cl₂ / -78 °C

2: 87 percent / PPTS / methanol

3: 96 percent / Bu₄NF / tetrahydrofuran

4: 1.) BuLi / 1.) THF, -78 deg C

5: toluene / Irradiation

6: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C

7: 79 percent / NaH / tetrahydrofuran

8: 1.) HCl, 2.) DBU / 1.) CH₂Cl₂, MeOH, 2.) toluene, reflux

9: 76 percent / Na(Hg), Na₂HPO₄ / methanol / 0.17 h / -40 °C

With hydrogenchloride; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; dimethylsulfide; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1016/0040-4039(92)80026-G

upstream raw materials:

2-acetyl-9-azabicyclo[4.2.1]non-2-ene-9-carboxylic acid methyl ester

(1S,6S)-1-(9-Aza-bicyclo[4.2.1]non-2-yl)-ethanone

(+/-)-2-acetyl-9-(tert-butoxycarbonyl)-9-azabicyclo<4.2.1.>non-2-ene

t-butyl-1-(9-azabicyclo<4.2.1>-non-2-ene-2-yl)ethanone carbamate

Downstream raw materials:

(+/-)-anatoxin-a

t-butyl-1-(9-azabicyclo<4.2.1>-non-2-ene-2-yl)ethanone carbamate

Refernces

• 1、 Newcombe,Simpkins. "A concise asymmetric synthesis of (-)-anatoxin-a using an enantioselective enolisation strategy". . p. 831 - 832. Retrieved 1995.
• 2、 Hjelmgaard, Thomas,Sotofte, Inger,Tanner, David. "Total synthesis of pinnamine and anatoxin-a via a common intermediate. A caveat on the anatoxin-a endgame". . p. 5688 - 5697. Retrieved 2007/10/03.
• 3、 Parsons, Philip J.,Camp, Nicholas P.,Edwards, Neil,Ravi Sumoreeah. "Synthesis of (±)-anatoxin-α and analogues". . p. 309 - 315. Retrieved 2007/10/03.