1-Benzyl-3-bromo-1-azoniatricyclo[2.2.1.0(2,6)]heptanebromide

Base Information

• Chemical Name: 1-Benzyl-3-bromo-1-azoniatricyclo[2.2.1.0(2,6)]heptanebromide
• CAS No.: 258264-42-5
• Molecular Formula: Br*C₁₃H₁₅BrN
• Molecular Weight: 345.077
• DSSTox Substance ID: DTXSID40379787
• Mol file: 258264-42-5.mol

Synonyms:258264-42-5;1-BENZYL-3-BROMO-1-AZONIATRICYCLO[2.2.1.0(2,6)]HEPTANEBROMIDE;1-benzyl-3-bromo-1-azoniatricyclo[2.2.1.02,6]heptane;bromide;1-benzyl-3-bromo-1-azoniatricyclo[2.2.1.0~2,6~]heptane bromide;1-Azoniatricyclo[2.2.1.02,6]heptane,3-bromo-1-(phenylmethyl)-, bromide (9CI);DTXSID40379787;1-Cyclobutene-1-carboxaldehyde, 2-chloro-;1-Benzyl-3-bromo-1-azatricyclo[2.2.1.0~2,6~]heptan-1-ium bromide

Chemical Property of 1-Benzyl-3-bromo-1-azoniatricyclo[2.2.1.0(2,6)]heptanebromide

Chemical Property:

• PSA: 0.00000
• LogP: -0.48600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 344.95508
• Heavy Atom Count: 16
• Complexity: 286

Purity/Quality:

98% ^*data from raw suppliers

1-Benzyl-3-bromo-1-azoniatricyclo[2.2.1.0~2,6~]heptane bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C[N+]3(C1C3C2Br)CC4=CC=CC=C4.[Br-]

Technology Process of 1-Benzyl-3-bromo-1-azoniatricyclo[2.2.1.0(2,6)]heptanebromide

There total 1 articles about 1-Benzyl-3-bromo-1-azoniatricyclo[2.2.1.0(2,6)]heptanebromide 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:

N-benzyl-2-azanorborn-5-ene (112375-05-0,150851-98-2) → 3-bromo-1-benzyl-1-azoniatricyclo[2.2.1.02,6]heptane bromide (258264-42-5)

Guidance literature:

With bromine; In dichloromethane; acetonitrile; at -78 - 20 ℃;

DOI:10.1021/jo0492564

Reference yield:

3-bromo-1-benzyl-1-azoniatricyclo[2.2.1.02,6]heptane bromide (258264-42-5) → syn-2-azabicyclo[2.2.1]heptane-7-carboxylic acid ethyl ester (745836-21-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / Red-Al / toluene; tetrahydrofuran / 2 h / -10 °C

2: 66 percent / 18-crown-6 / dimethylformamide / 24 h / 110 °C

3: HCl / H₂O / 65 h / 90 °C

4: SOCl₂ / 6 h / 40 °C

5: 0.5 h / 20 °C

6: 46 percent / NaOEt; HMPA / ethanol / 24 h / 65 °C

7: 61 percent / H₂ / Pd/C / methanol

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; thionyl chloride; 18-crown-6 ether; hydrogen; sodium ethanolate; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo0492564

Reference yield:

3-bromo-1-benzyl-1-azoniatricyclo[2.2.1.02,6]heptane bromide (258264-42-5) → anti-2-azabicyclo[2.2.1]heptane-7-carboxylic acid ethyl ester (745836-21-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / Red-Al / toluene; tetrahydrofuran / 2 h / -10 °C

2: 66 percent / 18-crown-6 / dimethylformamide / 24 h / 110 °C

3: HCl / H₂O / 65 h / 90 °C

4: SOCl₂ / 6 h / 40 °C

5: 0.5 h / 20 °C

6: 67 percent / H₂ / Pd/C / methanol / 24 h

With hydrogenchloride; thionyl chloride; 18-crown-6 ether; hydrogen; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium on activated charcoal; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo0492564

upstream raw materials:

N-benzyl-2-azanorborn-5-ene

Downstream raw materials:

syn-2-azabicyclo[2.2.1]heptane-7-carboxylic acid ethyl ester

anti-2-azabicyclo[2.2.1]heptane-7-carboxylic acid ethyl ester

Refernces