104713-12-4

Basic information

• Product Name: (R)-1-PHENYL-2-PROPEN-1-OL
• Synonyms: (R)-1-PHENYL-2-PROPEN-1-OL;(R)-ALPHA-VINYLBENZYL ALCOHOL;(r)-α-vinylbenzyl alcohol;(1R)-1-Phenyl-2-propene-1-ol;(R)-1-Phenylallyl alcohol;(R)-α-Vinylbenzenemethanol;(R)-1-Phenyl-2-propen-1-ol technical, >=95% (sum of enantiomers, GC)
• CAS NO: 104713-12-4
• Molecular Formula: C₉H₁₀O
• Molecular Weight: 134.18
• Mol File: 104713-12-4.mol

Chemical Properties

• Appearance: /
• Density: 1.021 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.543
• Storage Temp.: −20°C
• CAS DataBase Reference: (R)-1-PHENYL-2-PROPEN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-PHENYL-2-PROPEN-1-OL(104713-12-4)
• EPA Substance Registry System: (R)-1-PHENYL-2-PROPEN-1-OL(104713-12-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 104713-12-4(Hazardous Substances Data)

Upstream product

• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 69562-10-3 1-phenyl-3-phenylseleno-1-propene 
• 1826-67-1 vinyl magnesium bromide 
• 100-52-7 benzaldehyde 
• 1119-22-8 divinyl zinc 
• 139706-26-6 C₂₄H₃₂OSe 
• 114395-16-3 [(2S,3S)-3-phenyloxiran-2-yl]methyl 4-methylbenzenesulfonate 
• 168326-76-9 (E)-cinnamyl o-nitrophenyl selenide 
• 155394-01-7 (1R,2R)-1-phenyl-2-<(R)-p-tolylsulfinyl>-3-(trimethylsilyl)-1-propanol 
• 4541-87-1 cis-1-phenylpropene oxide 
• 4392-24-9 Cinnamyl bromide 
• 2687-12-9 cinnamyl chloride 
• 3536-96-7 vinylmagnesium chloride 

Downstream Products

• 214280-43-0 Diphenyl-bis-((R)-1-phenyl-allyloxy)-silane 
• 1565-74-8 (R)-1-phenyl-1-propanol 
• 255043-87-9 (R)-(+)-1-phenyl-prop-2-enyl methyl carbonate 
• 444575-90-0 (R)-(+)-tert-butyl 1-phenylprop-2-en-1-yl carbonate 
• 1402974-60-0 (S)-benzyl(1-phenylallyl)sulfane 
• 87156-77-2 C₁₆H₁₆S 
• 1402974-82-6 C₁₁H₁₁ClO₂ 
• 104023-33-8 Cinnamylchloracetat 
• 3198-15-0 (1R,2S)-(-)-norephedrine hydrochloride 
• 53643-20-2 (1R,2R)-norephedrine hydrochloride 
• 164468-30-8 (1'S)-phenyl 2'-propenyl 2-butynoate 
• 444575-89-7 (S)-(-)-tert-butyl 1-phenylprop-2-en-1-yl carbonate 
• 1200132-98-4 C₁₃H₁₄O₄ 
• 1402974-81-5 C₁₁H₁₁ClO₂ 

Relevant articles and documents

Synthesis of - and -Bisferrocenyl> Diselenides and Their Application to Asymmetric Selenoxide Elimination and Sigmatropic Rearrangement

Novel optically-active bisferrocenyl> diselenides ( and ), each of which possesses two axial and two central elements of chirality, have been prepared by lithiation of commercially available chiral ferrocenes, followed by reaction with elemental selenium and air oxidation, in 77-80percent isolated yields.The structure of the -bisferrocenyl diselenide has been fully characterized by X-ray crystallography.Six chiral ferrocenyl vinylic selenides and six chiral allylic ferrocenyl selenides have been newly prepared by reaction of the diselenides with the corresponding propiolate derivatives and allylic halides.The oxidation of the vinylic selenides with m-chloroperbenzoic acid in various organic solvents produces axially chiral allenecarboxylic esters via asymmetric selenoxide elimination in 27-59percent chemical yields with high enantioselectivities (up to 89percent ee).Similar treatment of the allylic selenides afforded the corresponding chiral allylic alcohols via asymmetric sigmatropic rearrangement in 28-82percent chemical yields with high enantioselectivities (up to 89percent ee).The observed high enantioselectivities indicate that oxidation proceeds diastereoselectively, that the resultant chiral selenoxides are slow to racemize, and also that selenoxide elimination and sigmatropic rearrangement proceed with little loss of optical activity.

Asymmetric [2,3]sigmatropic rearrangement of optically active allylic selenides

Oxidation of an optically active allylic selenide derived from L-proline 1 with m-chloroperbenzoic acid afforded the corresponding chiral allylic alcohol 3 via asymmetric [2,3]sigmatropic rearrangement with fair enantioselectivity (up to 66% e.e.).

Characterization of a Self-Sufficient Cytochrome P450 Monooxygenase from Deinococcus apachensis for Enantioselective Benzylic Hydroxylation

A self-sufficient cytochrome P450 monooxygenase from Deinococcus apachensis (P450DA) was identified and successfully overexpressed in Escherichia coli BL21(DE3). P450DA would be a member of the CYP102D subfamily and assigned as CYP102D2 according to the phylogenetic tree and sequence alignment. Purification and characterization of the recombinant P450DA indicated both NADH and NADPH could be used by P450DA as a reducing cofactor. The recombinant E. coli (P450DA) strain was functionally active, showing excellent enantioselectivity for benzylic hydroxylation of methyl 2-phenylacetate. Further substrate scope studies revealed that P450DA is able to catalyze benzylic hydroxylation of a variety of compounds, affording the corresponding chiral benzylic alcohols in 86–99 % ee and 130–1020 total turnover numbers.

Asymmetric [2,3] sigmatropic rearrangement via chiral selenoxide with Sharpless oxidants

The Sharpless oxidation of some aryl cinnamyl selenides afforded a chiral 1-phenyl-2-propen-1-ol via asymmetric [2,3] sigmatropic rearrangement in a moderate to high enantiomeric excess (up to 92% e.e.). The enantioselectivity was found to be enhanced remarkably by the introduction of the o-nitro group to an arylseleno moiety of the substrate and the use of diisopropyl tartrate (DIPT) ligand in the Sharpless oxidant. In the rearrangement step two possible transition states (TS(exo) and TS(endo)) are conceivable in which TS(endo) was revealed to be more stable by 4.2 kcal/mol than TS(exo) from the extended-Huckel calculation.

Enantioselective benzylic hydroxylation with pseudomonas monteilii TA-5: A simple method for the syntheses of (R)-benzylic alcohols containing reactive functional groups

Highly enantioselective benzylic hydroxylations of benzene derivatives (1-4) containing reactive functional groups were achieved for the first time with Pseudomonas monteilii TA-5 as biocatalyst, giving the corresponding (R)-benzylic alcohols 5-8 in 93-99% ee as the only products. Preparative biotransformations were demonstrated by the biohydroxylation of 1 and 2 with resting cells of P monteilii TA-5 to afford (R)-5 in 94% ee and 66% yield and (R)-6 in 94% ee and 56% yield, respectively. The highly enantioselective biohydroxylations represent a simple access to (R)-benzylic alcohols containing reactive functional groups that are useful pharmaceutical intermediates and versatile chiral building blocks.

One-pot transformation of p-toluenesulfonates of 2,3-epoxy alcohols into allylic alcohols

A convenient and efficient method for the synthesis of synthetically useful non-racemic allylic alcohols from 4-methylbenzenesulfonates of non- racemic 2,3-epoxy alcohols is described. Satisfactory yields are obtained by treatment of 4-methylbenzenesulfonates of non-racemic 2,3-epoxy alcohols with potassium iodide followed by zinc powder and ammonium chloride in a one-pot manner. The method has been successfully applied to the synthesis of a key building block of C30-C37 botryococcenes.

Enantioselective Synthesis of Cinnamyl-1-Phenyl-2-Propenyl Ether: A Metabolite of Marine Green Algal Species Caulerpa Racemosa

The enantioselective synthesis of title compound has been achieved using a new enzyme acyl system and a mild PT catalysed etherification.The absolute configuration of natural compound has been established as R-(+) by 1H NMR analysis of MTPA esters of the

Microscale determination of the absolute configuration of α-aryl- substituted alcohols by the CD exciton chirality method

The absolute configurations of a broad spectrum of aryl alcohols 1 have been determined for the first time by the CD exciton chirality method. The configurational assignment is additionally verified by computer modeling and lipase-catalyzed acetylation of the racemic alcohols. The CD-spectroscopic data have revealed that the S enantiomers of the benzoate derivatives 2 display a positive first Cotton effect and the R enantiomers a negative one at around 228 nm. Thus, the sense of the first Cotton effect of the benzoate derivative 2 allows a reliable assignment of the absolute configuration of the corresponding alcohol 1.

Enantioselective Preparation of sec. Alcohols from Aldehydes and Dialkyl Zinc Compounds, Generated in situ from Grignard Reagents, Using Substoichiometric Amounts of TADDOL-Titanates

Using the Schlenk trick (precipitation of MgX2 from etheral solutions by the addition of 1,4-dioxane) mixtures of a Grignard reagent RMgX (X = Cl, Br, I) and 0.5 equiv.ZnCl2 in Et2O can be converted to zinc alkyls R2Zn which in turn are added with enantioselectivities of up to 99:1 to aliphatic and aromatic aldehydes in the presence of Ti(OCHMe2)4 and a chiral titanate derived from an α,α,α',α'-tetraaryl-1,3-dioxolane-4,5-dimethanol (TADDOL).Grignard reagents containing remote double bonds, benzene rings, or acetal groups can also be employed.Different TADDOLs are compared with respect to their usefulness in this kind of enantioselective reactions.

A Chiral Metal-Organic Material that Enables Enantiomeric Identification and Purification

We show that CMOM-3S, a previously unreported porous crystalline metal-organic material that exhibits intrinsic homochirality, serves as a general-purpose chiral crystalline sponge (CCS) and a chiral stationary phase (CSP) for gas chromatography (GC). The properties of CMOM-3S are enabled by nano-sized channels connected to adaptable molecular recognition sites that mimic enzyme-binding sites. Further, CMOM-3S is composed of inexpensive components, facile to prepare, and requires only trace amounts of analyte. When coupled with the thermal and hydrolytic stability of CMOM-3S, these features mean that a coated fused silica capillary column in which CMOM-3S serves as a CSP is both more versatile and more robust than three benchmark commercial columns. That the enantiomer with the longer GC retention time is consistently captured in CCS experiments enables CMOM-3S to serve as a powerful tool to enable both chiral purification and enantiomer identification.