(2S)-2-[(2-allylphenoxy)methyl]oxirane

Base Information

• Chemical Name: (2S)-2-[(2-allylphenoxy)methyl]oxirane
• CAS No.: 81840-59-7
• Molecular Formula: C12H14O2
• Molecular Weight: 190.242
• DSSTox Substance ID: DTXSID70359532
• Nikkaji Number: J475.259G
• Wikidata: Q82140781
• Mol file: 81840-59-7.mol

Synonyms:(2S)-2-[(2-allylphenoxy)methyl]oxirane;81840-59-7;SCHEMBL7092232;DTXSID70359532;[S,(+)]-2alpha-[[2-(2-Propenyl)phenoxy]methyl]oxirane

Chemical Property of (2S)-2-[(2-allylphenoxy)methyl]oxirane

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 190.099379685
• Heavy Atom Count: 14
• Complexity: 191

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCC1=CC=CC=C1OCC2CO2
• Isomeric SMILES: C=CCC1=CC=CC=C1OC[C@@H]2CO2

Technology Process of (2S)-2-[(2-allylphenoxy)methyl]oxirane

There total 11 articles about (2S)-2-[(2-allylphenoxy)methyl]oxirane 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: 100.0%

(2S)-glycidyl-3-nitrobenzenesulfonate (1314092-54-0) + o-Allylphenol (1745-81-9) → (S)1-(2’-allylphenoxy)-2,3-epoxypropane (81840-59-7)

Guidance literature:

o-Allylphenol; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 0.5h; Inert atmosphere;

(2S)-glycidyl-3-nitrobenzenesulfonate; In N,N-dimethyl-formamide; mineral oil; at 60 ℃;

DOI:10.1021/jm2008562

Reference yield: 65.0%

(2s)-(+)-glycidyl 3-nitrobenzenesulfonate (115314-14-2) + o-Allylphenol (1745-81-9) → (S)1-(2’-allylphenoxy)-2,3-epoxypropane (81840-59-7)

Guidance literature:

o-Allylphenol; With potassium carbonate; In acetone; Inert atmosphere; Reflux;

(2s)-(+)-glycidyl 3-nitrobenzenesulfonate; In acetone; for 21h; Inert atmosphere; Reflux;

DOI:10.1021/acs.jmedchem.9b00595

Reference yield: 43.4%

1-(2-allylphenoxy)-2,3-epoxypropane (4638-04-4) → (S)1-(2’-allylphenoxy)-2,3-epoxypropane (81840-59-7) + (R)-3-(2'-allylphenoxy)-propane-1,2-diol

Guidance literature:

With Bacillus megaterium epoxide hydrolase; In aq. phosphate buffer; di-isopropyl ether; at 25 ℃; pH=7; Enzymatic reaction;

DOI:10.1002/anie.201402653

upstream raw materials:

(R)-1-(2-Allyl-phenoxy)-3-chloro-propan-2-ol

1-(2-allylphenoxy)-2,3-epoxypropane

1-(2-allyl-phenoxy)-3-chloro-propan-2-ol

Acetic acid 2-(2-allyl-phenoxy)-1-chloromethyl-ethyl ester

Downstream raw materials:

(S)-tert-butyl 2-(3-(2-allylphenoxy)-2-hydroxypropylamino)ethylcarbamate

(S)-13-amino-1-(2-(prop-2-en-1-yl)phenyl)-1,8,11-trioxa-5-azatridecan-3-ol

N-[-(R)-1,2,3,4-tetrahydronaphth-2-yl]-(S)-2-hydroxy-3-(2-allylphenoxy)propanamine

(S)-alprenolol

Refernces

• 1、 Kong, Xu-Dong,Ma, Qian,Zhou, Jiahai,Zeng, Bu-Bing,Xu, Jian-He. "A smart library of epoxide hydrolase variants and the top hits for synthesis of (S)-β-blocker precursors". supporting information. p. 6641 - 6644. Retrieved 2014/07/08.
• 2、 Baker, Jillian G.,Adams, Luke A.,Salchow, Karolina,Mistry, Shailesh N.,Middleton, Richard J.,Hill, Stephen J.,Kellam, Barrie. "Synthesis and characterization of high-affinity 4,4-difluoro-4-bora-3a,4a- diaza-s-indacene-labeled fluorescent ligands for human β-adrenoceptors". experimental part. p. 6874 - 6887. Retrieved 2011/12/15.