Gephyrotoxin

Base Information

• Chemical Name: Gephyrotoxin
• CAS No.: 55893-12-4
• Molecular Formula: C₁₉H₂₉NO
• Molecular Weight: 287.445
• UNII: 01N796R81A
• DSSTox Substance ID: DTXSID401029722
• Nikkaji Number: J11.075B
• Wikipedia: Gephyrotoxin
• Wikidata: Q5548689
• Mol file: 55893-12-4.mol

Synonyms:(1S,3aS,5aS,6S(Z),9aR,10R)dodecahydro-6-(2- penten-4-yl)pyrrolo(1,2-a)quinoline-1-ethanol;gephyrotoxin;gephyrotoxin 287C;Pyrrolo(1,2-a)quinoline-1-ethanol, dodecahydro-6-(2-penten-4-ynyl)-, (1S-(1alpha,3abeta,5aalpha,6alpha(Z),9aalpha))-

Chemical Property of Gephyrotoxin

Chemical Property:

• Melting Point: 231-232° (dec)
• Boiling Point: 408.9°Cat760mmHg
• Flash Point: 183.3°C
• PSA: 23.47000
• Density: 1.06g/cm³
• LogP: 3.29790
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 287.224914549
• Heavy Atom Count: 21
• Complexity: 421

Purity/Quality:

GEPHYROTOXIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CC=CCC1CCCC2C1CCC3N2C(CC3)CCO
• Isomeric SMILES: C#C/C=C\C[C@H]1CCC[C@H]2[C@@H]1CC[C@H]3N2[C@H](CC3)CCO

Technology Process of Gephyrotoxin

There total 35 articles about Gephyrotoxin 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,3aR,5aR,6R,9aS)-1-[(methoxycarbonyl)methyl]-6-[(Z)-pent-2-en-4-ynyl]dodecahydropyrrolo[1,2-a]quinoline → gephyrotoxin (55893-12-4)

Guidance literature:

(1R,3aR,5aR,6R,9aS)-1-[(methoxycarbonyl)methyl]-6-[(Z)-pent-2-en-4-ynyl]dodecahydropyrrolo[1,2-a]quinoline; With diisobutylaluminium hydride; In diethyl ether; hexane; at -78 ℃; for 1h;

With methanol; sodium tetrahydroborate; In diethyl ether; hexane; at -78 - 20 ℃; for 1h;

DOI:10.1021/acs.orglett.7b03381

Reference yield:

(4aR,5R,8aS)-1-(tert-butoxycarbonyl)-5-[2-(tertbutyldimethylsilyloxy)ethyl]decahydroquinoline → gephyrotoxin (55893-12-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: sodium periodate; ruthenium(IV) oxide hydrate / ethyl acetate; water / 2 h

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C

2.2: 1.5 h / 20 °C

3.1: lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 24 h / Reflux

4.1: sodium cyanoborohydride / dichloromethane / 0.25 h

4.2: 3 h / -42 °C

5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 1.25 h / 0 - 20 °C

5.2: 1 h / 0 - 20 °C

6.1: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C

7.1: tetrahydrofuran / 20 °C

8.1: bismuth(lll) trifluoromethanesulfonate; water / acetonitrile / 5 h / 20 °C

8.2: 4 h / 20 °C

9.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1 h / -78 °C

9.2: 0.25 h / -78 °C

9.3: 1.5 h / -78 - 20 °C

10.1: trifluoroacetic acid / dichloromethane / 1 h

11.1: sodium methylate / methanol / Reflux

12.1: diisobutylaluminium hydride / hexane; diethyl ether / 1 h / -78 °C

12.2: 1 h / -78 - 20 °C

With bismuth(lll) trifluoromethanesulfonate; sodium periodate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; ruthenium(IV) oxide hydrate; water; tert.-butyl lithium; sodium methylate; diisobutylaluminium hydride; sodium cyanoborohydride; Dess-Martin periodane; 9-bora-bicyclo[3.3.1]nonane; trifluoroacetic acid; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; acetonitrile; pentane; 7.1: |Wittig Olefination;

DOI:10.1021/acs.orglett.7b03381

Reference yield:

(4aR,5R,8aS)-1-(tert-butoxycarbonyl)-5-[2-(tertbutyldimethylsilyloxy)ethyl]-2-oxodecahydroquinoline → gephyrotoxin (55893-12-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C

1.2: 1.5 h / 20 °C

2.1: lithium chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 24 h / Reflux

3.1: sodium cyanoborohydride / dichloromethane / 0.25 h

3.2: 3 h / -42 °C

4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 1.25 h / 0 - 20 °C

4.2: 1 h / 0 - 20 °C

5.1: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C

6.1: tetrahydrofuran / 20 °C

7.1: bismuth(lll) trifluoromethanesulfonate; water / acetonitrile / 5 h / 20 °C

7.2: 4 h / 20 °C

8.1: tert.-butyl lithium / tetrahydrofuran; pentane / 1 h / -78 °C

8.2: 0.25 h / -78 °C

8.3: 1.5 h / -78 - 20 °C

9.1: trifluoroacetic acid / dichloromethane / 1 h

10.1: sodium methylate / methanol / Reflux

11.1: diisobutylaluminium hydride / hexane; diethyl ether / 1 h / -78 °C

11.2: 1 h / -78 - 20 °C

With bismuth(lll) trifluoromethanesulfonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; water; tert.-butyl lithium; sodium methylate; diisobutylaluminium hydride; sodium cyanoborohydride; Dess-Martin periodane; 9-bora-bicyclo[3.3.1]nonane; trifluoroacetic acid; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetonitrile; pentane; 6.1: |Wittig Olefination;

DOI:10.1021/acs.orglett.7b03381

Refernces

• 1、 Piccichè, Miriam,Pinto, Alexandre,Griera, Rosa,Bosch, Joan,Amat, Mercedes. "Enantioselective Total Synthesis of (+)-Gephyrotoxin 287C". . p. 6654 - 6657. Retrieved 2017.