bicyclo[2.2.1]hept-5-ene-2,3-diol

Base Information

• Chemical Name: bicyclo[2.2.1]hept-5-ene-2,3-diol
• CAS No.: 20224-38-8
• Molecular Formula: C7H10 O2
• Molecular Weight: 126.155
• Mol file: 20224-38-8.mol

Synonyms:5-Norbornene-2,3-diol,exo,exo- (8CI); Bicyclo[2.2.1]hept-5-ene-2,3-diol, (exo,exo)-; NSC 107386;exo,exo-5-Norbornene-2,3-diol

Chemical Property of bicyclo[2.2.1]hept-5-ene-2,3-diol

Chemical Property:

• Vapor Pressure: 0.0198mmHg at 25°C
• Boiling Point: 223.2°C at 760 mmHg
• Flash Point: 105.6°C
• Density: 1.364g/cm³

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of bicyclo[2.2.1]hept-5-ene-2,3-diol

There total 6 articles about bicyclo[2.2.1]hept-5-ene-2,3-diol 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: 70.0%

quadricyclo[2.2.1.0.0]heptane (278-06-8) → bicyclo[2.2.1]hept-5-ene-2,3-diol (20224-38-8)

Guidance literature:

With oxygen; rose bengal; In methanol; at 0 ℃; for 2h; Irradiation;

DOI:10.1246/cl.1993.129

Reference yield: 55.0%

bicyclo[2.2.1]hepta-2,5-diene (121-46-0) → bicyclo[2.2.1]hept-5-ene-2,3-diol (20224-38-8)

Guidance literature:

bicyclo[2.2.1]hepta-2,5-diene; With potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide; In water; acetone; at 40 ℃; for 14h; Inert atmosphere;

With sodium dithionate; In water; acetone; at 25 ℃; for 0.5h; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/acs.joc.6b02594

Reference yield: 35.0%

bicyclo[2.2.1]hepta-2,5-diene (121-46-0) → 5,6-bis-endo-dihydroxy-bicyclo[2.2.1]hept-2-ene (20224-39-9) + bicyclo[2.2.1]hept-5-ene-2,3-diol (20224-38-8)

Guidance literature:

Product distribution; oxidation with Pseudomonas BM₂ and other mutant;

DOI:10.1039/c39900000204

upstream raw materials:

bicyclo[2.2.1]hepta-2,5-diene

quadricyclo[2.2.1.0.0]heptane

Downstream raw materials:

cyclopenta-1,3-diene

(E)-Ethene-1,2-diol

(Z)-ethane-1,2-diol

3a,4,7,7a-tetrahydro-4,7-methanobenzo[d][1,3]dioxol-2-one

Refernces

• 1、 Sano, Hiromi,Sugai, Soji. "Synthesis of (+/-)-Carbocyclic Analogue of Spirohydantoin Nucleoside". . p. 4635 - 4646. Retrieved 1995.
• 2、 Higashibayashi, Shuhei,Masud Reza,Sakurai, Hidehiro. "Stereoselective cyclotrimerization of enantiopure iodonorbornenes catalyzed by Pd nanoclusters for C 3 or C 3 v symmetric syntris(norborneno)benzenes". supporting information; experimental part. p. 4626 - 4628. Retrieved 2010/09/18.