3-Phenyl-2-propen-l-ol

Phenyl-2-propen-l-ol [104-54-1], commonly referred to as cinnamyl alcohol, is a colorless crystalline soHd with a sweet balsamic odor that is reminiscent of hyacinth. Its occurrence in nature is widespread as, for example, in Hyacinth absolute (Hyacinthus orientalis) (42), the leaf and bark oils of cinnamon Cinnamomum cassia, Cinnamomum lancium, etc), and Guava fmit [Psidiumguajava L.) (43). In many cases it is also encountered as the ester or in a bound form as the glucoside. 

Coniferyl aicohol [4-hydroxy-3-methoxy-cinnamyl alcohol, 3-(4-hydroxy-3-methoxy-phenyl)-2-propen-l-ol] [458-35-5] M 180.2, m 73-75°, b 163-165°/3mm, pK 9.54. It is... 

ACETATE], 32 1 Propene, 2-methyl-, 35 2-Propen-l-ol, 2-bromo 3-phenyl-, acetate, 35... 

Phenyl-2-propenoic acid, e279 3-Phenyl-2-propen-l-ol, c282 3-Phenyl-2-propenoyl chloride, c280 3-Phenylpropyl alcohol, pi46 Phenyl propyl ketone, b619... 

Chem. Abstr. Name 3-Phenyl-2-propen-l-ol, 2-aminobenzoate lUPAC Systematic Name Anthranilic acid, cinnamyl ester Synonyms Cinnamyl alcohol anthranilate 3-phenyl-2-propenyl 2-aminobenzoate 3-phenyl-2-propenyl anthranilate... 

A cationic Ir complex possessing phosphanodihydrooxazole 26 is usable for asymmetric hydrogenation of allylic alcohols. (E)-2-Methyl-3-phenyl-2-propen-l-ol can be converted in CH2C12 containing 1 mol % of the Ir complex to the saturated product in 95% yield and 96% ee (Scheme 1.26) [141]. The process is used in the enantioselective synthesis of the artificial fragrance filial. 

The asymmetric oxidation of sulphides to chiral sulphoxides with t-butyl hydroperoxide is catalysed very effectively by a titanium complex, produced in situ from a titanium alkoxide and a chiral binaphthol, with enantioselectivities up to 96%342. The Sharpless oxidation of aryl cinnamyl selenides 217 gave a chiral 1-phenyl-2-propen-l-ol (218) via an asymmetric [2,3] sigmatropic shift (Scheme 4)343. For other titanium-catalysed epoxidations, see Section V.D.l on vanadium catalysis. 

Phenyl-2-propen-l-ol has been investigated as part of an FIK study of 3-phenylpropanal [931] (Sect. 6.4.2). It was proposed that the... 

The 2-methyl-3-phenylpropanal is 90% pure by GLC. The product mixture contains 6% of another isomer, 2-methyl-2-phenylpropanal, and a small amount of 2-phenyl-2-propen-l-ol. A completely pure sample of the aldehyde is readily obtained by stirring the crude aldehyde with excess saturated aqueous sodium bisulfite solution for several hours, filtering the solid bisulfite adduct, washing with ether, and liberating the aldehyde with excess aqueous sodium bicarbonate. Redistillation gives the completely pure aldehyde in about 60% yield. 

PROPEN-l-OL see AF 500 2-PROPEN-1-ONE see ADROOO 2-PROPEN-1 -ONE, 3-(4-METHYLPHENYL)-l -PHENYL- see NGF762 2-PROPENOPHENONE see PMQ250... 

The asymmetric [2,3]sigmatropic rearrangement of several other allyl aryl selenides has been reported, but only moderate selectivities are observed [27] (Scheme 18). The oxidation of cinnamyl and geranyl selenides derived from L-prolinol with MCPBA at -90°C afforded the chiral l-phenyl-2-propen-l-ol and linalool with moderate enantiomeric excess, respectively. 

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