(-)-(1S,2S)-1-phenylcyclohex-1-ene oxide

Base Information

• Chemical Name: (-)-(1S,2S)-1-phenylcyclohex-1-ene oxide
• CAS No.: 122210-64-4
• Molecular Formula: C₁₂H₁₄O
• Molecular Weight: 174.243
• Mol file: 122210-64-4.mol

Synonyms:

Chemical Property of (-)-(1S,2S)-1-phenylcyclohex-1-ene oxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1S,2S)-1-phenylcyclohex-1-ene oxide

There total 36 articles about (-)-(1S,2S)-1-phenylcyclohex-1-ene 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: 100.0%

1-Phenylcyclohexene (771-98-2) → 1-phenylcyclohexene oxide (5775-23-5,17540-04-4,122210-64-4,4829-01-0)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; for 15h; Ambient temperature;

DOI:10.1021/jo00001a021

Reference yield: 100.0%

1-Phenylcyclohexene (771-98-2) → (1R,2R)-1-phenyl-1-cyclohexene oxide (4829-01-0,5775-23-5,122210-64-4,17540-04-4)

Guidance literature:

With Oxone; potassium carbonate; acetic acid; ethylenediaminetetraacetic acid; deoxyfructose-derived ketone; In acetonitrile; at 0 ℃; for 1.5h; pH=9.3;

DOI:10.1016/j.tet.2005.03.123

Reference yield: 94.0%

1-Phenylcyclohexene (771-98-2) → (1S,6S)-1-phenyl-7-oxabicyclo[4.1.0]heptane (4829-01-0,17540-04-4,122210-64-4,5775-23-5)

Guidance literature:

With Oxone; sodium carbonate; C₂₃H₃₇N₂O₃⁽¹⁺⁾*HO^(1-); In water; acetonitrile; at 0 ℃; for 1.5h; Product distribution / selectivity;

upstream raw materials:

Perbenzoic acid

1-Phenylcyclohexene

methanol

(+/-)-2c-chloro-1r-phenyl-cyclohexanol-⁽¹⁾

Downstream raw materials:

(RS)-2-phenylcyclohexanone

1-phenyl-1-cyclopentanecarboxaldehyde

1-phenyl-1,2-cyclohexanediol

trans-1-Phenylcyclohexane-1,2-diol

Refernces

• 1、 Beigi, Maryam,Roller, Sebastian,Haag, Rainer,Liese, Andreas. "Polyglycerol-supported Co- and Mn-salen complexes as efficient and recyclable homogeneous catalysts for the hydrolytic kinetic resolution of terminal epoxides and asymmetric olefin epoxidation". . p. 2135 - 2141. Retrieved 2008.
• 2、 Canali, Laetitia,Cowan, Elaine,Deleuze, Herve,Gibson, Colin L.,Sherrington, David C.. "Polystyrene and polymethacrylate resin-supported Jacobsen's alkene epoxidation catalyst". . p. 2055 - 2066. Retrieved 2000.
• 3、 Brandes, Bridget D.,Jacobsen, Eric N.. "Highly Enantioselective, Catalytic Epoxidation of Trisubstituted Olefins". . p. 4378 - 4380. Retrieved 1994.
• 4、 Page,Rassias,Barros,Ardakani,Buckley,Bethell,Smith,Slawin. "Functionalized iminium salt systems for catalytic asymmetric epoxidation". . p. 6926 - 6931. Retrieved 2001.
• 5、 Bulman Page, Philip C.,Farah, Mohamed M.,Buckley, Benjamin R.,Chan, Yohan,Blacker, A. John. "Preparation of C 2-Symmetric Biaryl Bisiminium Salts and Their Use as Organocatalysts for Asymmetric Epoxidation". . p. 126 - 130. Retrieved 2016.
• 6、 Janssen, Kristien B. M.,Laquiere, Isabelle,Dehaen, Wim,Parton, Rudy F.,Vankelecom, Ivo F. J.,Jacobs, Pierre A.. "A dimeric form of Jacobsen's catalyst for improved retention in a polydimethylsiloxane membrane". . p. 3481 - 3487. Retrieved 1997.
• 7、 Aggarwal, Varinder K.,Lopin, Chrystel,Sandrinelli, Franck. "New insights in the mechanism of amine catalyzed epoxidation: Dual role of protonated ammonium salts as both phase transfer catalysts and activators of Oxone". . p. 7596 - 7601. Retrieved 2003.
• 8、 Liu, Shih-Yuan,Nocera, Daniel G.. "A simple and versatile method for alkene epoxidation using aqueous hydrogen peroxide and manganese salophen catalysts". . p. 1923 - 1926. Retrieved 2006.
• 9、 Yang, Ruiyun,Zhang, Yuecheng,Zhao, Jiquan. "Methyltrioxorhenium-catalyzed epoxidation of alkenes with hydrogen peroxide as an oxidant and 1-methyl-3-(butyl-4-sulfonate) imidazolium betaine as an additive". . p. 923 - 926. Retrieved 2011.
• 10、 Sartori, Giovanni,Armstrong, Alan,Maggi, Raimondo,Mazzacani, Alessandro,Sartorio, Raffaella,Bigi, Franca,Dominguez-Fernandez, Belen. "α-fluorotropinone immobilized on silica: A new stereoselective heterogeneous catalyst for epoxidation of alkenes with oxone". . p. 3232 - 3237. Retrieved 2003.