2-[(1R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]hept-2-enyl]pyridine

Base Information

• Chemical Name: 2-[(1R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]hept-2-enyl]pyridine
• CAS No.: 253783-05-0
• Molecular Formula: C15H19N
• Molecular Weight: 213.323
• DSSTox Substance ID: DTXSID40468761
• Nikkaji Number: J1.952.543K
• Wikidata: Q82296148
• Mol file: 253783-05-0.mol

Synonyms:253783-05-0;2-[(1R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]hept-2-enyl]pyridine;SCHEMBL5456453;DTXSID40468761;NUKWWIUNFJZQDK-ABAIWWIYSA-N;2-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl]pyridine

Chemical Property of 2-[(1R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]hept-2-enyl]pyridine

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 213.151749610
• Heavy Atom Count: 16
• Complexity: 328

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC1(C(=C2)C3=CC=CC=N3)C)C
• Isomeric SMILES: C[C@@]12CC[C@@H](C1(C)C)C=C2C3=CC=CC=N3

Technology Process of 2-[(1R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]hept-2-enyl]pyridine

There total 5 articles about 2-[(1R,4R)-1,7,7-trimethyl-2-bicyclo[2.2.1]hept-2-enyl]pyridine 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: 78.0%

2-bromo-pyridine (109-04-6) + (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl trifluoromethanesulfonate (108450-08-4) → (1R,4R)-2-(pyridin-2-yl)-1,7,7-trimethylbicyclo[2.2.1]-2-heptene (253783-05-0,84731-75-9)

Guidance literature:

2-bromo-pyridine; With n-butyllithium; zinc dibromide; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 0.75h;

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl trifluoromethanesulfonate; With 1,1'-bis-(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; hexane; at 70 ℃; for 15h;

DOI:10.1021/jo030383u

Reference yield: 78.0%

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl trifluoromethanesulfonate (108450-08-4) + pyridin-2-ylzinc(II) bromide → (1R,4R)-2-(pyridin-2-yl)-1,7,7-trimethylbicyclo[2.2.1]-2-heptene (253783-05-0,84731-75-9)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; lithium chloride; [Pd(dibenzylideneacetone)2]; In tetrahydrofuran; Heating;

DOI:10.1002/anie.200351936

Reference yield: 58.0%

thiocarbonic acid O-p-tolyl ester O-(1,7,7-trimethyl-2-pyridin-2-yl-bicyclo[2.2.1]hept-2-yl) ester → (1R,4R)-2-(pyridin-2-yl)-1,7,7-trimethylbicyclo[2.2.1]-2-heptene (253783-05-0,84731-75-9)

Guidance literature:

In benzene; for 1h; Heating;

DOI:10.1016/S0957-4166(99)00352-3

upstream raw materials:

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl trifluoromethanesulfonate

2-bromo-pyridine

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

(1R,2R,4R)-2-exo-hydroxy-2-endo-(pyridin-2-yl)-1,7,7-trimethylbicyclo[2.2.1]heptane

Downstream raw materials:

2-[(1S,2S,3R,4S)-3-(dicyclohexylphosphoryl)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]pyridine

2-[(1S,2S,3R,4S)-3-(diphenylphosphoryl)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]pyridine

2-[(1S,2S,3R,4S)-3-(diphenylphosphino)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]pyridine

2-[(1S,2S,3R,4S)-3-(dicyclohexylphosphino)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]pyridine

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