172295-01-1

Basic information

• Product Name: (E)-3-methyl-5-phenyl-4-penten-1-ol
• Synonyms: (E)-3-methyl-5-phenyl-4-penten-1-ol
• CAS NO: 172295-01-1
• Molecular Weight: 176.258
• Mol File: 172295-01-1.mol

Chemical Properties

• CAS DataBase Reference: (E)-3-methyl-5-phenyl-4-penten-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-methyl-5-phenyl-4-penten-1-ol(172295-01-1)
• EPA Substance Registry System: (E)-3-methyl-5-phenyl-4-penten-1-ol(172295-01-1)

Safety Data

• Hazardous Substances Data: 172295-01-1(Hazardous Substances Data)

Upstream product

• 267418-11-1 ethyl (4E)-3-methyl-5-phenylpent-4-enoate 

Downstream Products

• 172295-02-2 (E)-5-(benzylthio)-3-methyl-1-phenyl-1-pentene 
• 149713-23-5 2-phenyl-4-methyltetrahydrpyran 

Relevant articles and documents

Aluminium triflate catalysed cyclisation of unsaturated alcohols: novel synthesis of rose oxide and analogues

Aluminium trifluoromethanesulfonate was used as an efficient catalyst for the cycloisomerisation of several unsaturated alcohols into cyclic ethers such as rose oxide and some of its ether analogues.

Asymmetric synthesis of 1,2-dioxolane-3-acetic acids: Synthesis and configurational assignment of plakinic acid A

The first asymmetric synthesis of 1,2-dioxolane-3-acetic acids is reported. Key features include the stereoselective opening of enantiomerically enriched oxetanes by hydrogen peroxide, conversion of the resulting 4-hydroperoxy-2- alkanols to 3-alkoxy-1,2-dioxolanes, and Lewis acid mediated homologation of the latter with a thioester silyl ketene acetal. The approach is modeled on 3,5-dimethyl-5-hexadecyl-1,2-dioxolane-3-acetic acid (1a), an unnamed natural product, and an optimized strategy is applied to the synthesis of four stereoisomers of plakinic acid A (2), allowing a configurational assignment of this incompletely characterized natural product.

Substituent effects on the stereochemical course of electrophile- initiated tetrahydropyran-forming reactions: A possible stereoelectronic effect

A series of 4-penten-1,3-diol derivatives were prepared and treated with phenylselenenyl chloride to provide tetrahydropyrans. The stereochemical course of the reactions is consistent with a chair-like transition state in which the oxygen substituent at the 3-position largely occupies an axial site. A structurally related 3-methyl-4-penten-1-ol derivative gave a major product consistent with a chair transition state in which the methyl group occupies an equatorial site.

Cis-configurational unsaturated ester, process for producing the same, and fragrance composition containing the same

The present invention provides a cis-configurational unsaturated ester represented by the formula (1) (where R is a methyl group or a phenyl group, and n is 1 or 2) and also provides a fragrance composition containing the cis-configurational unsaturated ester in an effective amount. The cis-configurational unsaturated ester represented by the formula (1) can be produced by reacting a cyclic vinyl ether represented by the formula (2a) (where n is defined as above) with a Grignard reagent represented by the formula (3a)RMgX(3a)(where R is defined as above, and X is a chlorine atom, a bromine atom or an iodine atom) in the presence of a triarylphosphine and not more than 0.05 mol of a nickel compound per one mole of the cyclic vinyl ether represented by the formula (2a) to give a cis-configurational unsaturated alcohol represented by the formula (4a) (where n and R are defined as above); and subjecting this cis-configurational unsaturated alcohol to acylation with acetic acid or a derivative thereof to give the cis-configurational unsaturated esters represented by the formula (1).