Ethanone, 1-(9-azabicyclo[4.2.1]non-2-en-2-yl)- (9CI)

Base Information

• Chemical Name: Ethanone, 1-(9-azabicyclo[4.2.1]non-2-en-2-yl)- (9CI)
• CAS No.: 85514-42-7
• Molecular Formula: C10H15NO
• Molecular Weight: 165.235
• Mol file: 85514-42-7.mol

Synonyms:Ethanone, 1-(9-azabicyclo[4.2.1]non-2-en-2-yl)- (9CI);1-(9-azabicyclo[4.2.1]non-2-en-2-yl)-Ethanone

Chemical Property of Ethanone, 1-(9-azabicyclo[4.2.1]non-2-en-2-yl)- (9CI)

Chemical Property:

• PSA: 29.10000
• LogP: 1.74500

Purity/Quality:

1-(9-azabicyclo[4.2.1]non-2-en-2-yl)-Ethanone 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Ethanone, 1-(9-azabicyclo[4.2.1]non-2-en-2-yl)- (9CI)

There total 38 articles about Ethanone, 1-(9-azabicyclo[4.2.1]non-2-en-2-yl)- (9CI) 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: 65.0%

2-acetyl-9-azabicyclo[4.2.1]non-2-ene-9-carboxylic acid methyl ester (108585-39-3,145375-60-6) → (+/-)-Anatoxin A (64285-06-9,85514-42-7,92142-32-0)

Guidance literature:

With trimethylsilyl iodide; In acetonitrile; at 0 - 20 ℃;

DOI:10.1021/jo0506682

Reference yield:

(S)-Pyroglutaminol (17342-08-4) → (+/-)-Anatoxin A (64285-06-9,85514-42-7,92142-32-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 20 h / 20 °C

2.1: 51 percent / diethyl ether; tetrahydrofuran / 5 h / 20 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: 91 percent / tetrahydrofuran; hexane / 2.5 h / -78 - 0 °C

4.1: NaBH₄; aq. H₂SO₄ / 6.5 h / -20 °C

4.2: aq. H₂SO₄ / 1.5 h / 0 - 2 °C

5.1: O₃ / CH₂Cl₂ / 0.33 h / -78 °C

5.2: 1.17 g / PPh₃ / CH₂Cl₂ / -78 - 20 °C

6.1: 88 percent / LiCl; i-Pr₂NEt / acetonitrile / 6 h / 20 °C

7.1: HCl gas / methanol / -50 - 20 °C

7.2: 51 percent / DBU / toluene / 6.5 h / Heating

8.1: 65 percent / TMSI / acetonitrile / 0 - 20 °C

With hydrogenchloride; dmap; sodium tetrahydroborate; n-butyllithium; trimethylsilyl iodide; sulfuric acid; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetonitrile; 6.1: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/jo0506682

Reference yield:

(+/-)-2-acetyl-9-(tert-butoxycarbonyl)-9-azabicyclo<4.2.1.>non-2-ene (92998-50-0) → (+/-)-Anatoxin A (64285-06-9,85514-42-7,92142-32-0)

Guidance literature:

With hydrogenchloride; In ethyl acetate;

DOI:10.1021/ja00337a059

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

(+/-)-anatoxin-a

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

9-<<(S)-α-methylbenzyl>carbamoyl>anatoxin