(1R)-1-(Naphthalen-1-yl)ethane-1,2-diol

Base Information

• Chemical Name: (1R)-1-(Naphthalen-1-yl)ethane-1,2-diol
• CAS No.: 16651-65-3
• Molecular Formula: C12H12O2
• Molecular Weight: 188.226
• DSSTox Substance ID: DTXSID40563765
• Nikkaji Number: J1.278.473B
• Wikidata: Q82448244
• Mol file: 16651-65-3.mol

Synonyms:16651-65-3;(R)-1-(Naphthalen-1-yl)ethane-1,2-diol;(1R)-1-(Naphthalen-1-yl)ethane-1,2-diol;DTXSID40563765

Chemical Property of (1R)-1-(Naphthalen-1-yl)ethane-1,2-diol

Chemical Property:

• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 188.083729621
• Heavy Atom Count: 14
• Complexity: 181

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC=C2C(CO)O
• Isomeric SMILES: C1=CC=C2C(=C1)C=CC=C2[C@H](CO)O

Technology Process of (1R)-1-(Naphthalen-1-yl)ethane-1,2-diol

There total 2 articles about (1R)-1-(Naphthalen-1-yl)ethane-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:

(±)-1-(naphthalen-1-yl)ethane-1,2-diol (13603-64-0) + benzoyl chloride (98-88-4) → (+)-1-[(1S),2-dihydroxyethyl]naphthalene (209622-45-7) + (-)-1-[(1R),2-dihydroxyethyl]naphthalene (16651-65-3) + 2-hydroxy-2-(naphthalen-1-yl)ethyl benzoate + (R)-2-hydroxy-2-(naphthalen-1-yl)ethyl benzoate

Guidance literature:

With sodium carbonate; (S)-4,4-Br₂-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]stannepin; In tetrahydrofuran; water; at -10 ℃; for 17h; Title compound not separated from byproducts.;

DOI:10.1021/ol9908373

Reference yield:

(±)-1-(naphthalen-1-yl)ethane-1,2-diol (13603-64-0) + benzaldehyde (100-52-7) → (+)-1-[(1S),2-dihydroxyethyl]naphthalene (209622-45-7) + (-)-1-[(1R),2-dihydroxyethyl]naphthalene (16651-65-3) + 2-hydroxy-2-(naphthalen-1-yl)ethyl benzoate + (R)-2-hydroxy-2-(naphthalen-1-yl)ethyl benzoate

Guidance literature:

With 3,5,3',5'-tetra-tert-butyl-4,4'-diphenoquinone; BF₄^(1-)*C₂₁H₂₄N₃O⁽¹⁺⁾; caesium carbonate; In tetrahydrofuran; at -5 ℃; for 20h; enantioselective reaction; Molecular sieve; Schlenk technique; Sealed tube; Inert atmosphere; Resolution of racemate;

DOI:10.1021/acs.orglett.8b01029

Reference yield: 72.0%

4-biphenylboronic acid (5122-94-1) + (-)-1-[(1R),2-dihydroxyethyl]naphthalene (16651-65-3) → (R)-(-)-2-(4-biphenyl)-4-(1-naphthyl)-1,3,2-dioxaborolane

Guidance literature:

In chloroform; at 20 ℃;

DOI:10.1021/jo035803u

upstream raw materials:

(±)-1-(naphthalen-1-yl)ethane-1,2-diol

benzoyl chloride

benzaldehyde

Downstream raw materials:

(R)-2-hydroxy-2-(1-naphthyl)ethyl tosylate

N-((R)-2-Hydroxy-2-naphthalen-1-yl-ethyl)-4-methyl-N-thiazol-4-ylmethyl-benzenesulfonamide