(3R)-3-hydroxydodecanenitrile

Base Information

• Chemical Name: (3R)-3-hydroxydodecanenitrile
• CAS No.: 922527-71-7
• Molecular Formula: C₁₂H₂₃NO
• Molecular Weight: 197.321
• DSSTox Substance ID: DTXSID00580514
• Nikkaji Number: J2.398.687F
• Wikidata: Q82471363
• Mol file: 922527-71-7.mol

Synonyms:(3R)-3-hydroxydodecanenitrile;922527-71-7;DTXSID00580514

Chemical Property of (3R)-3-hydroxydodecanenitrile

Chemical Property:

• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 9
• Exact Mass: 197.177964357
• Heavy Atom Count: 14
• Complexity: 159

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCC(CC#N)O
• Isomeric SMILES: CCCCCCCCC[C@H](CC#N)O

Technology Process of (3R)-3-hydroxydodecanenitrile

There total 5 articles about (3R)-3-hydroxydodecanenitrile 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: 96.0%

potassium cyanide + (R)-(+)-1,2-epoxyundecane (236412-69-4,123493-71-0) → (R)-3-hydroxydodecanenitrile (922527-71-7)

Guidance literature:

In methanol; water; at 20 ℃; for 16h; Solvent; Temperature;

DOI:10.1039/c6ob01233g

Reference yield:

trimethylsilyl cyanide (7677-24-9) + (R)-(+)-1,2-epoxyundecane (236412-69-4,123493-71-0) → (R)-3-hydroxydodecanenitrile (922527-71-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50 ℃; for 16h;

DOI:10.1016/j.tetasy.2006.10.023

Reference yield:

(R)-undecane-1,2-diol (862848-62-2) → (R)-3-hydroxydodecanenitrile (922527-71-7)

Guidance literature:

Multi-step reaction with 3 steps

1: dibutyltin oxide; triethylamine / CH₂Cl₂ / 0.83 h / 20 °C

2: NaOH / methanol / 0.5 h / 0 °C

3: TBAF / tetrahydrofuran / 16 h / 50 °C

With sodium hydroxide; tetrabutyl ammonium fluoride; di(n-butyl)tin oxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.tetasy.2006.10.023

upstream raw materials:

trimethylsilyl cyanide

(R)-(+)-1,2-epoxyundecane

(R)-undecane-1,2-diol

toluene-4-sulfonic acid 2-hydroxy-undecyl ester

Downstream raw materials:

fellutamide B

(3R)-(-)-3-Hydroxydodecanoic acid