14212-54-5

Basic information

• Product Name: (1R,2R)-(+)-1-PHENYLPROPYLENE OXIDE
• Synonyms: (1R,2R)-(+)-1-PHENYLPROPYLENE OXIDE;Oxirane, 2-methyl-3-phenyl-, (2R,3R)- (9CI);1-phenylpropylene oxide;[(2R,3R)-3-Methyloxiranyl]benzene;[2R,3R,(+)]-3-Methyl-2-phenyloxirane;(1R,2R)-(+)-1-Phenylpropylene oxide 97%;(1,2-epoxypropyl)-,(1r,2r)-benzen;(1r,2r)-(+)-1-phenyl-1,2-epoxypropane
• CAS NO: 14212-54-5
• Molecular Formula: C₉H₁₀O
• Molecular Weight: 134.18
• Product Categories: EPOXYDE
• Mol File: 14212-54-5.mol
• Article Data: 191

Chemical Properties

• Boiling Point: 201-207 °C(lit.)
• Flash Point: 156 °F
• Appearance: /
• Density: 1.006 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.416mmHg at 25°C
• Refractive Index: n20/D 1.518(lit.)
• CAS DataBase Reference: (1R,2R)-(+)-1-PHENYLPROPYLENE OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-(+)-1-PHENYLPROPYLENE OXIDE(14212-54-5)
• EPA Substance Registry System: (1R,2R)-(+)-1-PHENYLPROPYLENE OXIDE(14212-54-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: DA0177000
• Hazardous Substances Data: 14212-54-5(Hazardous Substances Data)

Usage

Synthesis

A solution of 0.05 M Na2HPO4 (10.0 mL) was added to a 25-mL solution of undiluted commercial household bleach (Clorox). The pH of the resulting buffered solution (0.55 M in NaOCl) was adjusted to pH 11.3 by addition of a few drops of 1 M NaOH solution. This solution was cooled to 0 °C and then added at once to a 0 °C solution of the manganese catalyst (260 mg, 0.4 mmol) and cis-o-methylstyrene (1.18 g, 10 mmol) in 10 mL of CH2Cl2. The two-phase mixture was stirred at room temperature, and the reaction progress was monitored by TLC. After 3 h, 100 mL of hexane was added to the mixture and the brown organic phase was separated, washed twice with 100 mL of H2O and once with 100 mL of saturated NaCl solution, and then dried (Na2SO4). After solvent removal, the residue was purifified by flflash chromatography on silica gel to afford the epoxide (0.912 g, 68%). The ee of the epoxide was determined to be 84% by 1 H NMR analysis in the presence of Eu(hfc)3. Reference: Zhang, W.; Jacobsen, E. N. J. Org. Chem. 1991, 56, 2296?2298.

Uses

Chiral building block. Tool for studying enzyme hydrolysis rates.

InChI:InChI=1/C9H10O/c1-7-9(10-7)8-5-3-2-4-6-8/h2-7,9H,1H3/t7-,9+/m1/s1

Upstream product

• 766-90-5 cis-1-phenyl-1-propylene 
• 42151-56-4 (1S,2R)-(+)-N-methylephedrine 
• 135559-56-7 1-methyl-2-(methylthio)phenethyl alcohol 
• 135561-74-9 Toluene-4-sulfonic acid (1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl ester 
• 55380-59-1 ((1S,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-trimethyl-ammonium; bromide 
• 14212-53-4 (1S,2R)-cis-methylstyrene oxide 
• 873-66-5 1-propenylbenzene 
• 90-04-0 2-methoxy-phenylamine 
• 23355-97-7 1-phenylpropylene oxide 
• 62-53-3 aniline 
• 637-50-3 1-phenylpropene 
• 645-49-8 cis-stilben 
• 14222-20-9 1R,2R-N-methylpseudoephedrine 
• 160332-19-4 (-)-(1R,2R)-1-phenyl-2-chloro-1-propanol 

Downstream Products

• 1855-09-0 1-phenyl-1,2-propandiol 
• 135637-09-1 (1S,2R)-<1-2H>-1-phenylpropan-2-ol 
• 135637-10-4 (1S,2S)-<2-2H>-1-phenylpropan-1-ol 
• 14212-53-4 (1S,2R)-cis-methylstyrene oxide 
• 40421-52-1 (1R,2S)-1-phenylpropane-1,2-diol 
• 40560-98-3 (1S,2R)-1-phenylpropane-1,2-diol 
• 299-42-3 ephedrine 
• 39615-80-0 d,l-1-phenyl-2-methyl-4-penten-2-ol 
• 74333-46-3 anti-2-phenyl-5-hexen-3-ol 
• 74333-47-4 phenyl-2 hexene-5 ol-3 
• 120318-52-7 3-phenylhex-5-en-3-ol 
• 698-87-3 3-phenyl-2-propanol 
• 93-55-0 1-phenyl-propan-1-one 

Relevant articles and documents

Chiral salen Cr(iii) complexes encapsulated in thermo-responsive polymer nanoreactors for asymmetric epoxidation of alkenes in water

Chiral salen Cr(iii) (Cr(salen)) complexes were encapsulated in thermo-responsive polymer nanoreactors through folding an amphiphilic random copolymer of poly(N-isopropylacrylamide-co-IL/Cr(salen)) (poly(NIPAAM-co-IL/Cr(salen)) around Cr(salen) in water. The resulting catalytic nanoreactors exhibited several advantages over the traditional Cr(salen) system for asymmetric epoxidation of alkenes in water. First, they were dispersed in water, behaving as a quasi-homogeneous catalyst for the aqueous asymmetric epoxidation. Second, they effectively sequestered substrates from the surrounding environment, creating a highly concentrated environment for efficient catalysis. Third, water was excluded from the nanoreactor, minimizing the undesired hydrolysis of epoxides. As a result, the compartmentalized catalysts mediated aqueous asymmetric epoxidation with unprecedented yields (92-95%) and enantioselectivities (ee, 92-99%), whereas the traditional Cr(salen) catalyst was far less efficient (4-12% yield and 29-44% ee). Moreover, the catalytic nanoreactor could be facilely recovered for reuse by thermo-controlled separation. This work highlighted the potential of using folded polymers as a platform for developing highly efficient catalytic nanoreactors for a number of important organic transformations in water.

Increasing the Activity and Efficiency of Stereoselective Oxidations by using Decoy Molecules in Combination with Rate-Enhancing Variants of P450Bm3

The use of rate-accelerating variants of P450Bm3 coupled with decoy molecules is described, resulting in improved catalytic activity for hydroxylation and epoxidation reactions. Prochiral substrates were investigated to ascertain the effect of the mutant enzymes and the decoy molecules on the regio- and enantioselectivity of the oxidations. For the alkyl and alkene substituted benzene substrates tested, large improvements in the product formation activity over the wild-type enzyme were obtained. The product formation rates for the substrates tested ranged from 660 to 2210 nmol (nmol P450)?1 min?1 for variants containing the R47L and Y51F mutations. Although the regioselectivity was not significantly altered in most of the turnovers, some adjustment in the enantioselectivity was observed with smaller substrates. The addition of decoy molecules often resulted in improved enantioselectivity and counteracted reductions arising from the rate-accelerating mutants.

Chromium salen catalysed asymmetric alkene epoxidation. Influence of substituents at the 3,3'-positions on the salen rings

Any substituent at the 3,3'-positions is sufficient to give greater than 80% ee in the epoxidation of E-β-methylstyrene with chromium-salen complexes.

Asymmetric epoxidation by chiral ketones derived from carbocyclic analogues of fructose

A number of carbocyclic analogues of the fructose-derived ketone 1 have been prepared and investigated for asymmetric epoxidation. The studies show that the oxygen atom of the pyranose ring of 1 has an impact on the catalyst's activity and selectivity. Conformational, electronic, and steric effects are discussed.

High enantioselectivities in an (E)-alkene epoxidation by catalytically active chromium salen complexes. Insight into the catalytic cycle

Equation presented The epoxidation of (E)-β-methylstyrene mediated by an oxochromium salen complex yields the epoxide in 92% ee in stoichiometric mode, the highest ee yet reported for a metal-mediated epoxidation of an (E)-alkene. The effect of added donor ligands, previously substantial, has reached a ceiling with this complex. In catalytic mode a slightly reduced ee and higher yield is obtained, indicating both the presence of a second oxidation cycle and that the major oxidant reacts with its reduced form.

OPTICALLY PURE (S)- AND (R)-4,5-DIHYDRO-3H-4-METHYLDINAPHTHAZEPINES. APPLICATION TO THE SYNTHESIS OF NEW BIDENTATE LIGANDS WITH AXIAL ASYMMETRY

Easily available ephedrinium salts (S,1R,2S)- and (R,1R,2S)-2 on treatment with alkoxide base afford enantiomerically pure dihydroazepines (S)- and (R)-1, respectively, in quantitative yields.Cleavage of the corresponding dihydroazepinium quaternary salts

Enantioselective Epoxidation of Unfunctionalized Alkenes using Dioxiranes Generated In Situ

Using (+)-3-(trifluoroacetyl)camphor, or R(+)- and S(-)-3-methoxy-3-phenyl-4,4,4-trifluoro-butan-2-one as precursors for chiral dioxiranes generated in situ, the asymmetric epoxidation of prochiral alkenes trans-β-methylstyrene, trans-2-octene, and cis-2-

Asymmetric Epoxidation of Olefins Catalyzed by Substituted Aminobenzimidazole Manganese Complexes Derived from L-Proline

A family of manganese complexes [Mn(Rpeb)(OTf)2] (peb=1-(1-ethyl-1H-benzo[d]imidazol-2-yl)-N-((1-((1-ethyl-1H-benzo[d]imidazol-2-yl)methyl) pyrrolidin-2-yl)methyl)-N-methylmethanamine)) derived from L-proline has been synthesized and characterized, where R refers to the group at the diamine backbone. X-ray crystallographic analyses indicate that all the manganese complexes [Mn(Rpeb)(OTf)2] exhibit cis-α topology. These types of complexes are shown to catalyze the asymmetric epoxidation of olefins employing H2O2 as a terminal oxidant with up to 96% ee. Obviously, the R group of the diamine backbone can influence the catalytic activity and enantioselectivity in the asymmetric epoxidation of olefins. In particular, Mn(i-Prpeb)(OTf)2 bearing an isopropyl arm, cannot catalyze the epoxidation reaction with H2O2 as the oxidant. However, when PhI(OAc)2 is used as the oxidant instead, all the manganese complexes including Mn(i-Prpeb)(OTf)2 can promote the epoxidation reactions efficiently. Taken together, these results indicate that isopropyl substitution on the Rpeb ligand inhibits the formation of active Mn(V)-oxo species in the H2O2/carboxylic acid system via an acid-assisted pathway.

An effective strategy for creating asymmetric MOFs for chirality induction: A chiral Zr-based MOF for enantioselective epoxidation

Recently the construction of chiral MOFs (CMOFs) has been very challenging and complex. For the first time, we synthesized a chiral Zr-based MOF with l-tartaric acid by solvent-assisted ligand incorporation (SALI). We show that a CMOF can be postsynthetically generated by a simple method: incorporating chiral carboxylic groups on the achiral NU-1000. The post-synthesized chiral NU-1000 was used as an asymmetric support for producing a chiral catalyst with molybdenum catalytic active centers as Lewis acid sites. Enantioselective epoxidation of various prochiral alkens to epoxids by using [C-NU-1000-Mo] is comparable to that using other asymmetric homogeneous and heterogeneous catalysts, along with high enantiomeric excess and selectivity to epoxide (up to 100%). The CMOF could be reused in the styrene oxidation after five cycles without substantial deterioration in the CMOF crystallinity or catalytic performance.