(1R,2S,4R)-Norborna-5-ene-2-ol

Base Information

• Chemical Name: (1R,2S,4R)-Norborna-5-ene-2-ol
• CAS No.: 2890-98-4
• Molecular Formula: C7H10 O
• Molecular Weight: 110.156
• DSSTox Substance ID: DTXSID00450708
• Nikkaji Number: J181.722A
• Wikidata: Q82270511
• Mol file: 2890-98-4.mol

Synonyms:71030-15-4;(1R,2S,4R)-Norborna-5-ene-2-ol;SCHEMBL2428834;DTXSID00450708;(1r,4r,5s)-exo-5-hydroxy-2-norbornene;(1R,2S,4R)-bicyclo[2.2.1]hept-5-en-2-ol

Chemical Property of (1R,2S,4R)-Norborna-5-ene-2-ol

Chemical Property:

• Melting Point: 97.5-99.2 °C
• Boiling Point: 183.7°Cat760mmHg
• PKA: 14.85±0.20(Predicted)
• Flash Point: 62°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: 128

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CC(C1C=C2)O
• Isomeric SMILES: C1[C@@H]2C[C@@H]([C@H]1C=C2)O

Technology Process of (1R,2S,4R)-Norborna-5-ene-2-ol

There total 61 articles about (1R,2S,4R)-Norborna-5-ene-2-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%

(1RS,2SR,4RS)-bicyclo[2.2.1]hept-5-en-2-yl acetate (5257-37-4) → exo-5-norbornen-2-ol (2890-98-4,13080-90-5,16620-80-7,69769-90-0,71030-14-3,71030-15-4,87392-59-4,106928-44-3,694-97-3)

Guidance literature:

With sodium hydroxide; In methanol; for 4h; Heating;

DOI:10.1002/hlca.19800630409

Reference yield: 85.0%

bicyclo[2.2.1]hepta-2,5-diene (121-46-0) → exo-5-norbornen-2-ol (2890-98-4,13080-90-5,16620-80-7,69769-90-0,71030-14-3,71030-15-4,87392-59-4,106928-44-3,694-97-3)

Guidance literature:

bicyclo[2.2.1]hepta-2,5-diene; With [(S,S)-MeDuphos]Rh(NBD)OTf; benzo[1,3,2]dioxaborole; In tetrahydrofuran; at 20 ℃; for 3h;

With dihydrogen peroxide; sodium hydroxide; In water; optical yield given as %de; Inert atmosphere;

DOI:10.1002/adsc.200900013

Reference yield: 75.0%

(2-acetoxy-cis-exo-bicyclo[2.2.1]hept-5-en-3-yl)mercuric chloride (1077-98-1) → exo-5-norbornen-2-ol (2890-98-4,13080-90-5,16620-80-7,69769-90-0,71030-14-3,71030-15-4,87392-59-4,106928-44-3,694-97-3)

Guidance literature:

With sodium hydroxide; sodium amalgam; at 20 ℃; for 18h;

DOI:10.1016/S0040-4020(02)01276-0

upstream raw materials:

vinyl acetate

endo-5-norbornen-2-ol

(-)-<1S,4S>bicyclo<2.2.1>heptene-5 one-2

5-norbornenyl-2-acetate

Downstream raw materials:

(1S,2S,4R,5S,6S)-5-Chloro-6-phenylsulfanyl-bicyclo[2.2.1]heptan-2-ol

(1R,2R,4S,5S,6S)-6-Chloro-5-phenylsulfanyl-bicyclo[2.2.1]heptan-2-ol

exo-benzyl(bicyclo[2.2.1]hept-5-en-2-yl) ether

(+/-)-endo-2-norborneol