(1R,2R)-Cyclooct-5-ene-1,2-diol

Base Information

• Chemical Name: (1R,2R)-Cyclooct-5-ene-1,2-diol
• CAS No.: 203319-31-7
• Molecular Formula: C8H14O2
• Molecular Weight: 142.198
• DSSTox Substance ID: DTXSID80708113
• Mol file: 203319-31-7.mol

Synonyms:(1R,2R)-Cyclooct-5-ene-1,2-diol;203319-31-7;DTXSID80708113

Chemical Property of (1R,2R)-Cyclooct-5-ene-1,2-diol

Chemical Property:

• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 142.099379685
• Heavy Atom Count: 10
• Complexity: 106

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C(CCC=C1)O)O
• Isomeric SMILES: C1C[C@H]([C@@H](CCC=C1)O)O

Technology Process of (1R,2R)-Cyclooct-5-ene-1,2-diol

There total 12 articles about (1R,2R)-Cyclooct-5-ene-1,2-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: 99.0%

(1R,2R)-(Z)-1-hydroxycyclooct-4-enyl acetate → (Z)-(1R,2R)-cyclooct-5-ene-1,2-diol (203319-31-7)

Guidance literature:

With methanol; potassium carbonate; at 0 ℃; for 8h;

DOI:10.1248/cpb.46.17

Reference yield: 76.0%

(Z)-(1R,8R)-10,10-dimethyl-9,11-dioxabicyclo[6.3.0]undec-4-ene (37940-17-3) → (Z)-(1R,2R)-cyclooct-5-ene-1,2-diol (203319-31-7)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; water; at 70 ℃; for 72h;

DOI:10.1016/j.tetasy.2004.07.036

Reference yield: 57.0%

vinyl acetate (108-05-4,9003-20-7) + rac-(Z)-cyclooct-5-en-1,2-diol (31598-91-1,31603-51-7,36653-40-4,55519-21-6,69926-50-7,117468-07-2) → (1S,2S)-(Z)-cyclooct-5-ene-1,2-diol (69926-50-7) + (Z)-(1R,2R)-cyclooct-5-ene-1,2-diol (203319-31-7) + (1S,2S)-(Z)-1-hydroxycyclooct-4-enyl acetate + (1R,2R)-(Z)-1-hydroxycyclooct-4-enyl acetate

Guidance literature:

With Pseudomonas cepacia lipase; In tetrahydrofuran; at 50 ℃; Temperature; Inert atmosphere; Microwave irradiation; Enzymatic reaction;

DOI:10.3390/molecules19079215

upstream raw materials:

(Z)-(1R,8R)-10,10-dimethyl-9,11-dioxabicyclo[6.3.0]undec-4-ene

(5R,6R)-5,6-dihydroxydeca-1,9-diene

trans-1,5,9-decatriene

(4R,5R)-4,5-dibut-3-enyl-2,2-dimethyl-1,3-dioxacyclopentane

Downstream raw materials:

(1R,2R,6R)-9-oxabicyclo[3.3.1]-non-6-en-2-yl acetate

(1R,4R,5R,8R)-4,5-dibromo-10,10-dimethyl-9,11-dioxabicyclo[6.3.0]undecane

(1R,4S,5S,8R)-4,5-dibromo-10,10-dimethyl-9,11-dioxabicyclo[6.3.0]undecane

(1R,2R,3R)-9-oxabicyclo[3.3.1]non-6-en-2-yl N,N-dimethylthiocarbamate