9-Azabicyclo[4.2.1]non-2-ene-2-carboxaldehyde, (1R)- (9CI)

Base Information

• Chemical Name: 9-Azabicyclo[4.2.1]non-2-ene-2-carboxaldehyde, (1R)- (9CI)
• CAS No.: 125736-21-2
• Molecular Formula: C9H13NO
• Molecular Weight: 151.2056
• Mol file: 125736-21-2.mol

Synonyms:(1R)-anatoxinal;

Chemical Property of 9-Azabicyclo[4.2.1]non-2-ene-2-carboxaldehyde, (1R)- (9CI)

Chemical Property:

• Vapor Pressure: 0.00555mmHg at 25°C
• Boiling Point: 274°Cat760mmHg
• PKA: 9.59±0.40(Predicted)
• Flash Point: 122.6°C
• PSA: 29.10000
• Density: 1.123g/cm³
• LogP: 1.35490

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 9-Azabicyclo[4.2.1]non-2-ene-2-carboxaldehyde, (1R)- (9CI)

There total 8 articles about 9-Azabicyclo[4.2.1]non-2-ene-2-carboxaldehyde, (1R)- (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: 97.0%

(1R)-9-(tert-butoxycarbonyl)-2-formyl-9-azabicyclo<4.2.1>non-2-ene (125826-59-7) → (1R)-anatoxinal (125736-21-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jo00296a050

Reference yield:

(1R)-2-acetyl-9-(1-tert-butoxycarbonyl)-9-azobicyclo<4.2.1>-2-nonene (90741-53-0) → (1R)-anatoxinal (125736-21-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 1) KHMDS, 2) Et₃N / 1) THF, -78 deg C, 60 min, 2) -78 deg C, 45 minalp

2: MCPBA / hexane / 0.5 h / Ambient temperature

3: aq. HF / acetonitrile / 0.33 h / Ambient temperature

4: NaIO₄ / H₂O; methanol / 1 h / Ambient temperature

5: oxalyl chloride, DMF / benzene / 1 h / Ambient temperature

6: 1) 4-methylmorpholine / 1) DMF, r.t., 30 min, 2) THF, -10 deg C to r.t.

7: LiAlH₄ / tetrahydrofuran / 0.25 h / -10 °C

8: 97 percent / TFA / CH₂Cl₂ / 1 h / Ambient temperature

With 4-methyl-morpholine; sodium periodate; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen fluoride; potassium hexamethylsilazane; triethylamine; N,N-dimethyl-formamide; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetonitrile; benzene;

DOI:10.1021/jo00296a050

Reference yield:

(1R)-9-(tert-butoxycarbonyl)-2-(2-hydroxyacetyl)-9-azabicyclo<4.2.1>non-2-ene (125736-13-2) → (1R)-anatoxinal (125736-21-2)

Guidance literature:

Multi-step reaction with 5 steps

1: NaIO₄ / H₂O; methanol / 1 h / Ambient temperature

2: oxalyl chloride, DMF / benzene / 1 h / Ambient temperature

3: 1) 4-methylmorpholine / 1) DMF, r.t., 30 min, 2) THF, -10 deg C to r.t.

4: LiAlH₄ / tetrahydrofuran / 0.25 h / -10 °C

5: 97 percent / TFA / CH₂Cl₂ / 1 h / Ambient temperature

With 4-methyl-morpholine; sodium periodate; lithium aluminium tetrahydride; oxalyl dichloride; N,N-dimethyl-formamide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; benzene;

DOI:10.1021/jo00296a050

upstream raw materials:

(1R)-9-(tert-butoxycarbonyl)-2-formyl-9-azabicyclo<4.2.1>non-2-ene

(1R)-2-acetyl-9-(1-tert-butoxycarbonyl)-9-azobicyclo<4.2.1>-2-nonene

(1R)-9-(tert-butoxycarbonyl)-2-(chlorocarbonyl)-9-azabicyclo<4.2.1>non-2-ene

(1R)-9-(tert-butoxycarbonyl)-2-carboxy-9-azabicyclo<4.2.1>non-2-ene

Refernces