ChemicalBook CAS DataBase List 1-PHENYL-1-CYCLOPROPANOL

1-PHENYL-1-CYCLOPROPANOL synthesis

12synthesis methods

Product Name:1-PHENYL-1-CYCLOPROPANOL
CAS Number:29526-96-3
Molecular formula:C9H10O
Molecular Weight:134.18

4,4,5,5-tetramethyl-2-(1-phenylcyclopropyl)-1,3,2-dioxaborolane

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Yield:-

Reaction Conditions:

with phosphite;Pseudomonas fluorescens 4-hydroxyacetophenone monooxygenase;phosphite dehydrogenase;oxygen;NADPH in dimethyl sulfoxide; pH=7.5 at 25; for 24 h;aq. buffer;Enzymatic reaction;

Steps:

4.7. General procedure for enzymatic oxidation reactions
General procedure: To a flask (2 mL, Eppendorf containing a solution of the starting material (1 M in DMSO, 5 μL) were added Tris/HCl buffer at pH 7.5 (50 mM, 440 μL), phosphite solution (500 mM, 20 μL), NADPH (100 mM, 10 μL), PTDH (100 μM, 5 μL), and enzyme (BVMO) (100 μM, 20 μL). Reactions were shaken at 200 rpm and 30 °C (PAMO and M446G PAMO mutant) or 150 rpm and 25 °C (HAPMO and CHMO) for the time established. The reactions were stopped, extracted with EtOAc (3 × 0.5 mL), dried over Na₂SO₄, and analyzed by chiral HPLC. Control experiments in the absence of an enzyme were performed for all substrates tested, and no reaction was observed.

References:

Brondani, Patricia B.;Dudek, Hanna;Reis, Joel S.;Fraaije, Marco W.;Andrade, Leandro H. [Tetrahedron Asymmetry,2012,vol. 23,# 9,p. 703 - 708] Location in patent:experimental part

93-89-0 Synthesis