(R)-2-methyl-2-phenyloxirane

Base Information

• Chemical Name: (R)-2-methyl-2-phenyloxirane
• CAS No.: 100018-61-9
• Molecular Formula: C₉H₁₀O
• Molecular Weight: 134.178
• Mol file: 100018-61-9.mol

Synonyms:

Chemical Property of (R)-2-methyl-2-phenyloxirane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-methyl-2-phenyloxirane

There total 27 articles about (R)-2-methyl-2-phenyloxirane 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: 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

Reference yield: 80.0%

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) + (2S)-2-methyl-2-phenyloxirane (2404-43-5)

Guidance literature:

With C₂₆H₃₆F₆FeN₆O₆S₂; C₃₀H₄₄N₄O₈; dihydrogen peroxide; In water; acetonitrile; at -30 ℃; for 0.5h; Reagent/catalyst; enantioselective reaction;

DOI:10.1039/c7sc00099e

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:

2-Phenylpropanal

(S)-2-phenyl-1-propanol

(+)-(R)-2-phenylpropanol

(S)-2-phenyl-propionaldehyde

Refernces

• 1、 Fingerhut, Anja,Vargas-Caporali, Jorge,Leyva-Ramírez, Marco Antonio,Juaristi, Eusebio,Tsogoeva, Svetlana B.. "Biomimetic non-heme iron-catalyzed epoxidation of challenging terminal alkenes using aqueous H2O2 as an environmentally friendly oxidant". . . Retrieved 2019.
• 2、 Halterman, Ronald L.,Jan, Shyi-Tai,Nimmons, Heather L.,Standlee, David J.,Khan, Masood A.. "Synthesis and catalytic reactivity of D4-symmetric dinorbornabenzene-derived metallotetraarylporphyrins". . p. 11257 - 11276. Retrieved 1997.
• 3、 Karamé, Iyad,Tommasino, M. Lorraine,Lemaire, Marc. "Iridium-catalyzed alternative of the Meinwald rearrangement". . p. 7687 - 7689. Retrieved 2003.
• 4、 Farokhi, Afsaneh,Hosseini-Monfared, Hassan. "A recyclable Mn-porphyrin catalyst for enantioselective epoxidation of unfunctionalized olefins using molecular dioxygen". . p. 5032 - 5043. Retrieved 2016.
• 5、 Huang, Jing,Liu, Sirui,Ma, Yan,Cai, Jiali. "Chiral salen Mn (III) immobilized on ZnPS-PVPA through alkoxyl-triazole for superior performance catalyst in asymmetric epoxidation of unfunctionalized olefins". . p. 27 - 33. Retrieved 2019.
• 6、 Huang, Jing,Yuan, Li,Cai, Jiali,Chen, Xiaohong,Qi, Dengwei. "Layered crystalline chiral salen Mn(III) complexes immobilized on organic polymer-inorganic hybrid zinc phosphonate-phosphate as efficient and reusable catalysts for the unfunctionalized olefin epoxidation". . p. 4 - 8. Retrieved 2016.
• 7、 Leurs, Melanie,Dorn, Bjoern,Wilhelm, Sascha,Manisegaran, Magiliny,Tiller, Joerg. C.. "Multicore Artificial Metalloenzymes Derived from Acylated Proteins as Catalysts for the Enantioselective Dihydroxylation and Epoxidation of Styrene Derivatives". . p. 10859 - 10867. Retrieved 2018.
• 8、 Zhang, Huidong,Zhang, Yanmei,Li, Can. "Asymmetric epoxidation of unfunctionalized olefins catalyzed by Mn(salen) axially immobilized onto insoluble polymers". . p. 2417 - 2423. Retrieved 2005.
• 9、 Churakova, Ekaterina,Kluge, Martin,Ullrich, Rene,Arends, Isabel,Hofrichter, Martin,Hollmann, Frank. "Specific photobiocatalytic oxyfunctionalization reactions". . p. 10716 - 10719. Retrieved 2011.
• 10、 Zheng, Weiguo,Tan, Rong,Yin, Shenfu,Zhang, Yaoyao,Zhao, Guangwu,Chen, Yaju,Yin, Donghong. "Ionic liquid-functionalized graphene oxide as an efficient support for the chiral salen Mn(iii) complex in asymmetric epoxidation of unfunctionalized olefins". . p. 2092 - 2102. Retrieved 2015.