1-[(1R,5S)-8-azabicyclo[3.2.1]oct-2-en-2-yl]ethanone

Base Information

• Chemical Name: 1-[(1R,5S)-8-azabicyclo[3.2.1]oct-2-en-2-yl]ethanone
• CAS No.: 64603-83-4
• Molecular Formula: C₉H₁₃NO
• Molecular Weight: 151.208
• ChEMBL ID: CHEMBL2332145
• DSSTox Substance ID: DTXSID101226715
• Nikkaji Number: J427.063K
• Mol file: 64603-83-4.mol

Synonyms:CHEMBL2332145;64603-83-4;DTXSID101226715;BDBM50428368;1-(1R,5S)-8-Azabicyclo[3.2.1]oct-2-en-2-ylethanone

Chemical Property of 1-[(1R,5S)-8-azabicyclo[3.2.1]oct-2-en-2-yl]ethanone

Chemical Property:

• PSA: 29.10000
• LogP: 1.35490
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 151.099714038
• Heavy Atom Count: 11
• Complexity: 220

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CCC2CCC1N2
• Isomeric SMILES: CC(=O)C1=CC[C@@H]2CC[C@H]1N2

Technology Process of 1-[(1R,5S)-8-azabicyclo[3.2.1]oct-2-en-2-yl]ethanone

There total 15 articles about 1-[(1R,5S)-8-azabicyclo[3.2.1]oct-2-en-2-yl]ethanone 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: 90.0%

(2S,3S)-2,3-Bis-(4-methyl-benzoyloxy)-succinic acid; compound with (1R,5S)-1-(8-aza-bicyclo[3.2.1]oct-2-en-2-yl)-ethanone → (-)-Norferruginine (64603-83-4)

Guidance literature:

With ammonium hydroxide; In water;

DOI:10.1021/jo961920w

Reference yield:

(1R,2S,4S,5S)-4-acetyl-8-benzyl-2-(methoxycarbonyl)-8-azabicyclo<3.2.1>octane (172172-42-8) → (-)-Norferruginine (64603-83-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 91 percent / H₂ / Pd/C / methanol / 3.5 h / 2585.7 Torr / Ambient temperature

2: 1.) KHMDS, 2.) TMSCl, 3.) O₃, 4.) Me₂S

3: 1.) i-BuO₂CCl, 2.) N-hydroxy-2-thiopyridone, Et₃N, 3.) 2-methylpropanethiol

4: 1.) LDA, 2.) PhSeCl, 3.) NaIO₄

5: aq. KOH / propan-2-ol / 1.) 0 deg C, 40 min, 2.) room temperature, 36 h

6: 1.) isobutyl chloroformate, 2.) Et₃N / 1.) THF, -10 deg C, 20 min, 2.) CH₂Cl₂, -10 deg C -> room temperature, 4.5 h

7: 92 percent / MeLi / tetrahydrofuran; diethyl ether / 1.) -78 deg C, 5 min, 2.) -78 deg C -> 0 deg C, 1 h

8: TFA / CH₂Cl₂ / 3 h / Ambient temperature

With 1-hydroxy-2(1H)-pyridinethione; potassium hydroxide; sodium periodate; chloro-trimethyl-silane; Phenylselenyl chloride; dimethylsulfide; 2-methylpropanethiol-1; methyllithium; hydrogen; potassium hexamethylsilazane; ozone; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; isopropyl alcohol;

DOI:10.1021/jo9515081

Reference yield:

(1R,2R,4S,5S)-4-acetyl-8-benzyl-2-(methoxycarbonyl)-8-azabicyclo<3.2.1>octane (172277-44-0) → (-)-Norferruginine (64603-83-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 97 percent / H₂ / Pd/C / methanol / 3.5 h / 2585.7 Torr / Ambient temperature

2: 1.) KHMDS, 2.) TMSCl, 3.) O₃, 4.) Me₂S

3: 1.) i-BuO₂CCl, 2.) N-hydroxy-2-thiopyridone, Et₃N, 3.) 2-methylpropanethiol

4: 1.) LDA, 2.) PhSeCl, 3.) NaIO₄

5: aq. KOH / propan-2-ol / 1.) 0 deg C, 40 min, 2.) room temperature, 36 h

6: 1.) isobutyl chloroformate, 2.) Et₃N / 1.) THF, -10 deg C, 20 min, 2.) CH₂Cl₂, -10 deg C -> room temperature, 4.5 h

7: 92 percent / MeLi / tetrahydrofuran; diethyl ether / 1.) -78 deg C, 5 min, 2.) -78 deg C -> 0 deg C, 1 h

8: TFA / CH₂Cl₂ / 3 h / Ambient temperature

With 1-hydroxy-2(1H)-pyridinethione; potassium hydroxide; sodium periodate; chloro-trimethyl-silane; Phenylselenyl chloride; dimethylsulfide; 2-methylpropanethiol-1; methyllithium; hydrogen; potassium hexamethylsilazane; ozone; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; isopropyl alcohol;

DOI:10.1021/jo9515081

upstream raw materials:

(1R,5S)-2-acetyl-8-(tert-butoxycarbonyl)-8-azabicyclo<3.2.1>-2-octene

methyl (1R,5S)-8-<(1,1-dimethylethoxy)carbonyl>-8-azabicyclo<3.2.1>octa-2-ene-2-carboxylate

(1R,5S)-8-<(1,1-dimethylethoxy)carbonyl>-8-azabicyclo<3.2.1>octa-2-ene-2-carboxylic acid

(1R,5S)-8-(tert-butoxycarbonyl)-8-azabicyclo<3.2.1>octene-2-carboxylic acid isoxazolidide