6-bicyclo[2.2.1]hept-2-enyl acetate

Base Information

• Chemical Name: 6-bicyclo[2.2.1]hept-2-enyl acetate
• CAS No.: 5257-37-4
• Molecular Formula: C9H12O2
• Molecular Weight: 152.193
• European Community (EC) Number: 228-144-1
• NSC Number: 128686,29887
• DSSTox Substance ID: DTXSID40967002
• Nikkaji Number: J21.522H
• Mol file: 5257-37-4.mol

Synonyms:2-acetoxy-5-norbornene

Chemical Property of 6-bicyclo[2.2.1]hept-2-enyl acetate

Chemical Property:

• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 152.083729621
• Heavy Atom Count: 11
• Complexity: 208

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CC2CC1C=C2

Technology Process of 6-bicyclo[2.2.1]hept-2-enyl acetate

There total 13 articles about 6-bicyclo[2.2.1]hept-2-enyl acetate 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: 18.0%

2,4-dinitrobenzenesulfenyl chloride (528-76-7) + acetic acid (64-19-7,77671-22-8) + quadricyclo[2.2.1.0.0]heptane (278-06-8) → 3-acetoxynortricyclene (6555-48-2,127057-06-1,127127-98-4,127127-99-5) + Acetic acid (1R,2R,4R,5S)-5-acetoxy-7-(2,4-dinitro-phenylsulfanyl)-bicyclo[2.2.1]hept-2-yl ester (80698-20-0) + (1RS,2SR,4RS)-bicyclo[2.2.1]hept-5-en-2-yl acetate (5257-37-4) + Acetic acid (1R,3S,4S,5R)-5-(2,4-dinitro-phenylsulfanyl)-tricyclo[2.2.1.02,6]hept-3-yl ester (66965-67-1)

Guidance literature:

With lithium perchlorate; at 20 ℃; for 2h; Further byproducts given;

DOI:10.1021/jo00347a018

Reference yield: 9.0%

2,4-dinitrobenzenesulfenyl chloride (528-76-7) + quadricyclo[2.2.1.0.0]heptane (278-06-8) → 3-acetoxynortricyclene (6555-48-2,127057-06-1,127127-98-4,127127-99-5) + (1RS,2SR,4RS)-bicyclo[2.2.1]hept-5-en-2-yl acetate (5257-37-4) + (1S,4R,5S,6S)-5-Chloro-6-(2,4-dinitro-phenylsulfanyl)-bicyclo[2.2.1]hept-2-ene (66887-41-0) + (1S,3S,4R,5R)-3-Chloro-5-(2,4-dinitro-phenylsulfanyl)-tricyclo[2.2.1.02,6]heptane (71075-02-0) + (1S,3R,4R,5R)-3-Chloro-5-(2,4-dinitro-phenylsulfanyl)-tricyclo[2.2.1.02,6]heptane (73464-48-9) + Acetic acid (1R,3S,4S,5R)-5-(2,4-dinitro-phenylsulfanyl)-tricyclo[2.2.1.02,6]hept-3-yl ester (66965-67-1)

Guidance literature:

With lithium perchlorate; In acetic acid; at 20 ℃; for 0.0833333h; Product distribution; effect of LiCiO₄ and various solvents on products distribution;

DOI:10.1021/jo00347a018

Reference yield:

nortricyclane (279-19-6) + acetic acid (64-19-7,77671-22-8) → 3-Acetoxynortricyclen (6555-48-2,127127-98-4,127127-99-5) + 4-ethynylcyclopentene (330654-57-4) + 5-acetoxynorborn-2-ene (2890-95-1,5257-37-4,62667-88-3,83679-37-2,99295-40-6,99295-41-7,112836-09-6,6143-29-9)

Guidance literature:

Photolysis;

DOI:10.1021/jo005713e

upstream raw materials:

Essigsaeure<6endo-tosyloxy-2endo-norbornyl>ester

Essigsaeure-<6exo-tosyloxy-2endo-norbornyl>ester

norborn-5-en-2-one

2,4-dinitrobenzenesulfenyl chloride

Downstream raw materials:

(+/-)-endo-norborneol acetate

(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-ol

(1R,2R,4R)-endo-bicyclo[2.2.1]hept-5-en-2-ol

(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl acetate