(S)-alpha-Methylstyrene oxide

Base Information

• Chemical Name: (S)-alpha-Methylstyrene oxide
• CAS No.: 2404-43-5
• Molecular Formula: C9H10O
• Molecular Weight: 134.178
• DSSTox Substance ID: DTXSID20469675
• Nikkaji Number: J881.476G
• Wikidata: Q82297495
• Mol file: 2404-43-5.mol

Synonyms:(S)-alpha-Methylstyrene oxide;2404-43-5;(s)-alpha-methyl-styrene oxide;SCHEMBL5855213;DTXSID20469675;MRXPNWXSFCODDY-SECBINFHSA-N

Chemical Property of (S)-alpha-Methylstyrene oxide

Chemical Property:

• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 134.073164938
• Heavy Atom Count: 10
• Complexity: 127

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CO1)C2=CC=CC=C2
• Isomeric SMILES: C[C@@]1(CO1)C2=CC=CC=C2

Technology Process of (S)-alpha-Methylstyrene oxide

There total 47 articles about (S)-alpha-Methylstyrene oxide 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: 98.0%

dimethylsulfoxonium methylide (70775-39-2,5367-24-8) + acetophenone (98-86-2) → (2S)-2-methyl-2-phenyloxirane (2404-43-5)

Guidance literature:

With C₆₀H₃₆LaLi₃O₆; tris(2,4,6-trimethoxyphenyl)phosphine oxide; In tetrahydrofuran; at 20 - 23 ℃; for 12h; optical yield given as %ee; enantioselective reaction; Molecular sieve;

DOI:10.1021/ja803864p

Reference yield: 92.0%

(R)-1-phenyl-1,2-ethanediol (2406-22-6,4217-66-7,87760-50-7,35638-92-7) → (R)-2-methyl-2-phenyloxirane (2085-88-3,2404-43-5,21019-52-3,100018-61-9)

Guidance literature:

With dmap; triethylamine; p-toluenesulfonyl chloride; In dichloromethane; at 0 - 50 ℃; for 24h; Inert atmosphere;

DOI:10.1002/chem.201102913

Reference yield: 90.0%

isopropenylbenzene (98-83-9,6144-04-3,25014-31-7,42612-14-6) → (R)-2-methyl-2-phenyloxirane (2085-88-3,2404-43-5,21019-52-3,100018-61-9)

Guidance literature:

With sodium hypochlorite; ammonium acetate; In dichloromethane; at 0 ℃; for 5.5h; pH=11.3; optical yield given as %ee; enantioselective reaction; aq. phosphate buffer;

DOI:10.1002/aoc.1873

upstream raw materials:

(2R)-1-((S)-2-methoxymethylpyrrolidino)-2-phenyl-2-propanol

isopropenylbenzene

2-methyl-2-phenyloxirane

(R)-2-hydroxy-2-phenylpropyl 4-methylbenzenesulfonate

Downstream raw materials:

(2R)-2-methyl-2-phenyloxetane

2-Phenylpropanal

(S)-2-phenyl-1-propanol

(+)-(R)-2-phenylpropanol

Refernces

• 1、 Li, Yuedong,Fu, Xiangkai,Gong, Biwei,Zou, Xiaochuan,Tu, Xiaobo,Chen, Junxian. "Synthesis of novel immobilized tridentate Schiff base dioxomolybdenum(VI) complexes as efficient and reusable catalysts for epoxidation of unfunctionalized olefins". . p. 55 - 62. Retrieved 2010.
• 2、 Huang, Cheng,Lu, Qingquan,Ma, Wan,Qi, Xiaotian,Xu, Minghao,Zheng, Xuelian. "Epoxide Electroreduction". supporting information. p. 1389 - 1395. Retrieved 2022/01/19.
• 3、 Franssen, Maurice C. R.,Hollmann, Frank,Martínez-Montero, Lía,Paul, Caroline E.,Süss, Philipp,Schallmey, Anett,Tischler, Dirk. "Asymmetric azidohydroxylation of styrene derivatives mediated by a biomimetic styrene monooxygenase enzymatic cascade". . p. 5077 - 5085. Retrieved 2021/08/16.