190506-77-5

Basic information

• Product Name: Hydroperoxide, (1R)-1-phenylpropyl
• CAS NO: 190506-77-5
• Molecular Formula: C9H12O2
• Molecular Weight: 152.193
• Mol File: 190506-77-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Hydroperoxide, (1R)-1-phenylpropyl(CAS DataBase Reference)
• NIST Chemistry Reference: Hydroperoxide, (1R)-1-phenylpropyl(190506-77-5)
• EPA Substance Registry System: Hydroperoxide, (1R)-1-phenylpropyl(190506-77-5)

Safety Data

• Hazardous Substances Data: 190506-77-5(Hazardous Substances Data)

Upstream product

• 58687-91-5 (+/-)-1-phenyl-propyl hydroperoxide 
• 613-87-6 (S)-1-phenyl-1-propanol 

Downstream Products

• 103098-57-3 ((R)-1-phenyl-propyl)-trityl peroxide 

Relevant articles and documents

Kinetic resolution of chiral hydroperoxides: hydrogen-peroxide-mediated screening of peroxidase-active soil bacteria

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Asymmetric synthesis with the enzyme Coprinus peroxidase: Kinetic resolution of chiral hydroperoxides and enantioselective sulfoxidation

The enzyme Coprinus peroxidase (CiP) was employed for the kinetic resolution of racemic hydroperoxides 1 and the asymmetric sulfoxidation of prochiral sulfides 4. Eleven hydroperoxides 1a-k were reduced by CiP and guaiacol as reductant under conditions of kinetic resolution with enantioselectivities of up to >98% for the (S)-hydroperoxide 1 and 90% for the (R)-alcohol 2. In the absence of a reductant, the hydroperoxide 1a afforded with CiP enantiomerically enriched hydroperoxide la (ee up to 54%) and alcohol 2a (ee up to 40%), as well as ketone 3a (which is also formed simultaneously in all other reactions) and molecular oxygen. Catalase activity was established for CiP with hydrogen peroxide. When aryl alkyl sulfides 4 were used as oxygen acceptors, three products, sulfoxides 5, alcohols 2, and hydroperoxides 1, were obtained, all in enantiomerically enriched form. The highest ee value (89%) was achieved for the sulfoxide derived from naphthyl methyl sulfide (4f). Thus, CiP may be utilized for the asymmetric synthesis of optically active hydroperoxides 1, alcohols 2, and sulfoxides 5.