261919-07-7

Basic information

• Product Name: (3S,5E)-1-phenyl-5-heptene-3-ol
• Synonyms: (3S,5E)-1-phenyl-5-heptene-3-ol
• CAS NO: 261919-07-7
• Molecular Weight: 190.285
• Mol File: 261919-07-7.mol

Chemical Properties

• CAS DataBase Reference: (3S,5E)-1-phenyl-5-heptene-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,5E)-1-phenyl-5-heptene-3-ol(261919-07-7)
• EPA Substance Registry System: (3S,5E)-1-phenyl-5-heptene-3-ol(261919-07-7)

Safety Data

• Hazardous Substances Data: 261919-07-7(Hazardous Substances Data)

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 370581-91-2 20-((1'S)-hydroxy-(2'S)-methyl-3'-buten-1'-yl)-3-oxopregn-4-ene 
• 444808-75-7 20-((1'R)-hydroxy-(3'E)-penten-1'-yl)-3-oxopregn-4-ene 
• 4894-61-5 trans-but-2-enyl chloride 
• 83173-74-4 (3S,4R)-3-methyl-6-phenyl-1-hexen-4-ol 
• 25201-44-9 (1S,2S)-2-methyl-1-phenyl-3-buten-1-ol 

Downstream Products

• 909110-93-6 1-Methoxy-4-((E)-(S)-1-phenethyl-pent-3-enyloxymethyl)-benzene 
• 873851-02-6 (S)-5-(4-Methoxy-benzyloxy)-7-phenyl-heptane-2,3-diol 
• 873850-75-0 Acetic acid (2S,4R,5R,6S,10R,11S)-10-(tert-butyl-dimethyl-silanyloxy)-5,11-dimethyl-2-phenethyl-1,7-dioxa-spiro[5.5]undec-4-yl ester 
• 740853-00-3 (3S)-3-(4-methoxybenzyloxy)-5-phenylpentanal 

Relevant articles and documents

Highly (E)-selective BF3·Et2O-promoted allylboration of chiral nonracemic α-Substituted allylboronates and analysis of the origin of stereocontrol

(Figure presented) δ-Methyl-substituted homoallylic alcohols 2 were prepared in 71-88% yield, E:Z >30:1 and 93% to >95% ee via BF 3·Et2O-promoted allylboration with α-Me-allylboronate 1. The origin of high (E)-selectivity is proposed

Enantioselective and catalytic method for α-crotylation of aldehydes with a kinetic self-refinement of stereochemistry

A practical and catalytic approach towards enantioenriched homoallylic alcohols, using a two-step protocol combining a highly enantioselective Lewis base-catalyzed addition of crotyltrichlorosilanes to an auxiliary non-chiral aromatic aldehyde, was presen

Solid-phase synthesis of [5.5]-spiroketals

An efficient and reliable multi-step synthesis of 251 natural product-like [5.5]-spiroketals on solid supports has been developed. As central key step, a double intramolecular hetero-Michael (DIHMA) reaction to alkynones was applied. The sequence allows for introduction of numerous substituents on the scaffold and for variation of stereochemistry. [5.5]-Spiroketals bearing an additional ketone were obtained in high overall yields. Further diversification was achieved by reduction of the ketone and reductive amination using polymer-supported borohydride, Grignard reaction and conversion to oxime derivatives in the solution phase.

An unusual approach to the synthesis of enantiomerically cis linear homoallylic alcohols based on the steric interaction mechanism of camphor scaffold

Camphor is used as the chiral auxiliary for the enantioselective synthesis of cis linear homoallylic alcohols. A range of catalysts, aldehydes, and solvents were investigated to obtain the optimum yield, enantioselectivity, and cis olefinic geometry.

The first example of enantioselective allyl transfer from a linear homoallylic alcohol to an aldehyde

(Formula Presented) The first example of enantioselective linear homoallylic alcohol transfer reaction was revealed. In all cases, the whole rearrangement is thermodynamically favorable and a steric effect is the driving force of this reaction. The preservation of the stereocenter and olefin geometry together with the isolation of γ-adduct homoallylic alcohols in one isomeric form have warranted the proposed mechanism.

Homoallylic sterol/indium(III) Lewis acid: A novel enantioselective allylation system exhibiting α-regioselectivity

A homoallylic sterol/indium(III) Lewis acid reagent system was utilized for the enantioselective and α-regioselective allylation of various aldehydes.

New and stereoselective synthesis of 1,4-disubstituted buten-4-ols (homoallylic alcohol α-adducts) from the corresponding γ-isomers (3,4-disubstituted buten-4-ols) via an acid-catalyzed allyl-transfer reaction with aldehydes

The γ-adducts of homoallylic alcohols 3, derived from aldehydes via the usual reaction with common allylic metals 1, were converted to the corresponding α-adducts 6 by an acid-catalyzed allyl-transfer reaction. In the allyl-transfer reaction, anti-and syn