Bicyclo[2.2.1]hept-2-en-7-ol

Base Information

• Chemical Name: Bicyclo[2.2.1]hept-2-en-7-ol
• CAS No.: 694-70-2
• Molecular Formula: C7H10O
• Molecular Weight: 110.1537
• DSSTox Substance ID: DTXSID50927112
• Nikkaji Number: J132.806I
• Mol file: 694-70-2.mol

Synonyms:Bicyclo[2.2.1]hept-2-en-7-ol;53783-87-2;13118-70-2;Bicyclo(2.2.1)hept-2-en-7-ol, syn-;Bicyclo(2.2.1)hept-2-en-7-ol, anti-;BICYCLO(2.2.1)HEPT-2-EN-7-OL;694-70-2;7-norbornenol;SCHEMBL7862601;SCHEMBL13038561;DTXSID50927112;PSKWDFVNXXATCG-UHFFFAOYSA-N;bicyclo[2.2.1]hept-5-en-7-ol;Bicyclo[2.2.1]hept-2-en-7-ol-anti-;Bicyclo[2.2.1]hept-2-en-7-ol-syn-

Chemical Property of Bicyclo[2.2.1]hept-2-en-7-ol

Chemical Property:

• Vapor Pressure: 0.183mmHg at 25°C
• Melting Point: 116-117 °C
• Boiling Point: 186.7°C at 760 mmHg
• PKA: 14.61±0.20(Predicted)
• Flash Point: 62.9°C
• PSA: 20.23000
• Density: 1.153g/cm³
• LogP: 0.94330
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 110.073164938
• Heavy Atom Count: 8
• Complexity: 114

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2C=CC1C2O

Technology Process of Bicyclo[2.2.1]hept-2-en-7-ol

There total 20 articles about Bicyclo[2.2.1]hept-2-en-7-ol 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: 91.0%

7-Acetoxynorbornadien (13426-49-8) → ant-7-norbornenol (694-70-2)

Guidance literature:

With lithium aluminium tetrahydride;

DOI:10.1002/anie.201604112

Reference yield: 56.0%

bicyclo[2.2.1]hepta-2,5-diene (121-46-0) → ant-7-norbornenol (694-70-2) + tricyclo[2.2.1.02,6]heptan-3-ol (695-04-5,70981-39-4,70981-40-7)

Guidance literature:

With water; 1-Cyanonaphthalene; In acetonitrile; for 12h; Irradiation;

DOI:10.1016/S0040-4039(00)81315-5

Reference yield: 45.0%

exo-2,3-epoxynorbornane (278-74-0) → syn-bicyclo<2.2.1>hept-2-en-7-ol (694-70-2,13118-70-2,53783-87-2,95404-23-2,95404-24-3)

Guidance literature:

exo-2,3-epoxynorbornane; With phenylmagnesium bromide; In diethyl ether; for 3h; Heating / reflux;

With water; In diethyl ether;

upstream raw materials:

anti-C₇H₉Br

bicyclo[2.2.1]hepta-2,5-diene

7-(2-Chloro-ethoxy)-bicyclo[4.1.0]hept-2-ene

7-norbornenone

Downstream raw materials:

anti-C₇H₉Br

tetrabenzo[5.5]fulvalene

exo-3,3-Fluorenylidenetricyclo<3.2.1.0^2,4>octan-anti-8-ol

(3aR,4R,7S,7aR,8S)-3,3-Diphenyl-3a,4,7,7a-tetrahydro-3H-4,7-methano-indazol-8-ol

Refernces

• 1、 Weiss,Snyder. "". . p. 1627. Retrieved 1970.
• 2、 Gray,G.A. et al.. "-". . p. 200 - 204. Retrieved 1971.
• 3、 Jordan, Robert W.,Le Marquand, Paul,Tam, William. "Ruthenium(II)-catalyzed [2+2] cycloadditions of anti 7-substituted norbornenes". . p. 80 - 86. Retrieved 2008/09/17.
• 4、 Abboud, Jose-Luis M.,Alkorta, Ibon,Davalos, Juan Z.,Mueller, Paul,Quintanilla, Esther,Rossier, Jean-Claude. "Influence of carbocation stability in the gas phase on solvolytic reactivity: Beyond bridgehead derivatives". . p. 3786 - 3796. Retrieved 2007/10/03.