104516-09-8

Basic information

• Product Name: (R)-1-phenyl-2,3-butanedien-1-ol
• CAS NO: 104516-09-8
• Molecular Weight: 146.189
• Mol File: 104516-09-8.mol
• Article Data: 75

Chemical Properties

• CAS DataBase Reference: (R)-1-phenyl-2,3-butanedien-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-phenyl-2,3-butanedien-1-ol(104516-09-8)
• EPA Substance Registry System: (R)-1-phenyl-2,3-butanedien-1-ol(104516-09-8)

Safety Data

• Hazardous Substances Data: 104516-09-8(Hazardous Substances Data)

Upstream product

• 6089-04-9 3-(tetrahydropyran-2'-yloxy)propyne 
• 100-52-7 benzaldehyde 
• 13361-64-3 trimethyl(propargyl)silane 
• 106-96-7 propargyl bromide 
• 624-65-7 2-propynyl chloride 
• 297767-01-2 bis(dimethylpropargylsilyl)methane 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 33415-29-1 trichloro(prop-2-ynyl)silane 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 29430-64-6 1,1-Diisopropylbut-3-ynol 
• 32904-84-0 4-hydroxy-4-phenyl-2-butynyl methyl ether 
• 693-04-9 butyl magnesium bromide 
• 50-00-0 formaldehyd 
• 4187-87-5 (R)-1-phenyl-2-propyn-1-ol 

Downstream Products

• 89538-83-0 (E)-1,3-Diphenyl-4-pyrrolidin-1-yl-but-2-en-1-ol 
• 54435-79-9 (E)-1,3-diphenyl-3-methyl-2-propen-1-one 
• 35632-82-7 [(1E)-3-phenylbuta-1,3-dien-1-yl]benzene 
• 69626-39-7 1-phenylbuta-2,3-dien-1-one 
• 80290-29-5 2-phenyl-3-(1-phenylvinyl)oxirane 
• 15121-75-2 3-methyl-5-phenylfuran-2-(5H)-one 
• 935749-22-7 carbonic acid tert-butyl ester 1-phenyl-buta-2,3-dienyl ester 
• 1083055-92-8 3-chloromethyl-5-phenyl-2(5H)-furanone 
• 1039769-83-9 3-butyl-2-(p-nitrophenyl)-4-(4'-phenyl-1',3'-butadien-3'(E)-2'-yl)-2,5-dihydrofuran 
• 1236304-75-8 (R)-3-(2-methoxymethoxy-4-methylphenyl)-1-phenylbut-2-en-1-ol 

Relevant articles and documents

Regio- and diastereoselective allenylation of aldehydes in aqueous media: Total synthesis of (+)-goniofufurone

The regio- and diastereoselectivities of metal-mediated allenylation of carbonyl compounds were investigated in aqueous media. Different metal mediators showed varied regioselectivities on product formation during propargylation-allenylation reactions of carbonyl compounds with simple propargyl bromide. Under the standard reaction conditions, the use of indium provided the highest regioselectivity, with a preference of formation of the homopropargyl alcohol. The use of tin and bismuth as the metal mediator provided slightly lower selectivities with the same preference. The use of zinc and cadmium as the mediators further lowered the product selectivity. The reactions of an alipathic aldehyde with simple propargyl bromide showed a lower selectivity than the reaction of an aromatic aldehyde in most cases, except for the use of tin or zinc (where comparable selectivities were observed). On the other hand, the reaction of terminal-substituted propargyl bromides with aldehydes mediated by indium showed a high regioselectivity in forming allenylation products. The indium-mediated allenylation of carbonyl compounds bearing an α-hydroxyl group also proceeded with a high diastereoselectivity, forming syn-diols predominantly in aqueous ethanol. The high diastereoselectivity in allenylation of α-hydroxyl-substituted aldehydes was attributed to the chelation effect exhibited by the α-hydroxyl substituent. Through the use of this highly diastereoselective allenylation, (+)-goniofufurone was synthesized from D'-glucurono-6,3-lactone.

Cobalt-Catalyzed C8-Dienylation of Quinoline-N-Oxides

An efficient Cp*CoIII-catalyzed C8-dienylation of quinoline-N-oxides was achieved by employing allenes bearing leaving groups at the α-position as the dienylating agents. The reaction proceeds by CoIII-catalyzed C?H activation of qui

A mild convenient Barbier-type allylation of aldehydes to homoallylic alcohols via iodide ion promoted stannylation of allylic bromides and chlorides with tin(II) chloride

Barbier-type allylation of aldehydes with allylic bromides and tin(II) chloride dihydrate is largely accelerated by adding stoichiometric or substoichiometric amounts of sodium iodide. This method has some merits such as lower temperature, shorter reaction time and/or more choices of solvents for the reaction. Moreover, the activation by the iodide ion enables the use of relatively unreactive allylic chlorides of various structural types (e.g., 3-chloro-2-chloromethylpropene as an isobutene dianion equivalent) and, thus, expands synthetic applicability of this reaction. The major role of the iodide salt is attributed to the in situ generation of the corresponding allylic iodide.

Studies on catalytic asymmetric Nozaki-Hiyama propargylation

(Equation Presented) Catalytic asymmetric Nozaki-Hiyama propargylation with ligand 1c proceeds with good to excellent enantioselectivity. Tuning of ligand 1 dramatically changes the enantioselectivity, and we propose models A and B to explain the change a

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Synthesis of Polyketide Stereoarrays Enabled by a Traceless Oxonia-Cope Rearrangement

Polyketide antibiotics bearing skipped polyols represent a synthetic challenge. A SiCl4-promoted oxonia-Cope rearrangement of syn,syn-2-vinyl-1,3-diols was developed to forge an array of 1,5-pentenediols, thus providing versatile motifs for the preparation of 1,2,3,5-stereoarrays in a highly stereoselective manner. Further exploration with Sn(OTf)2 realized the rearrangement of a cross-aldehyde which tactically warrants the utility of the current approach to access complex polyketides. The origin of high stereoselectivity is attributed to a chairlike anti-conformation of the oxonium ion intermediate.

ACTION DU PROPARGYLTRIMETHYLSILANE SUR LES DERIVES CARBONYLES EN PRESENCE DE FLUORURE DE TETRA-N-BUTYLAMMONIUM: NOUVELLE VOIE D'ACCES AUX ALCOOLS α-ALLENIQUES.

Propargyltrimethylsilane reacts with carbonyl compounds to produce α-allenic alcohols in the presence of tetra-n-butylammonium fluoride.

Palladium-catalyzed [3+2] annulation of allenyl carbinol acetates with C,N-cyclic azomethine imines

In this paper, a palladium-catalyzed [3+2] annulation of allenyl carbinol acetates with azomethine imines has successfully been developed under mild reaction conditions, affording biologically interesting tetrahydropyrazoloisoquinoline derivatives in high to excellent yields and with excellent stereoselectivity. The reaction follows a tandem [3+2] cycloaddition/allylation/elimination of AcOH pathway. Allenyl carbinol acetates also reacted well with in situ generated azomethine imine under cocatalysis of Ag(i)/Pd(0) catalysts in a similar reaction pathway.

Highly stereoselective kinetic resolution of α-allenic alcohols: An enzymatic approach

A highly efficient lipase AK-catalyzed direct kinetic resolution of a variety of α-allenic alcohols was developed. With the complementary to previous studies, the current reaction system is effective on a broad range of substituents (R1) at C(1), such as alkyl, aryl, alkenyl, and alkynyl groups. The Jones-Burgess empirical model was modified to interpret the reversed selectivity during the acetylation of secondary alcohol. The methyl group at C(2) of allenic alcohols implied a small structural adjustment in the catalytic triad of lipase AK, representing a potential direction for future site-directed mutagenesis.