122919-99-7

Basic information

• Product Name: (R)-(+)-1-phenylhexa-1,5-dien-3-ol
• CAS NO: 122919-99-7
• Molecular Weight: 174.243
• Mol File: 122919-99-7.mol
• Article Data: 92

Chemical Properties

• CAS DataBase Reference: (R)-(+)-1-phenylhexa-1,5-dien-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-1-phenylhexa-1,5-dien-3-ol(122919-99-7)
• EPA Substance Registry System: (R)-(+)-1-phenylhexa-1,5-dien-3-ol(122919-99-7)

Safety Data

• Hazardous Substances Data: 122919-99-7(Hazardous Substances Data)

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 107-37-9 allyltrichlorosilane 
• 106-95-6 allyl bromide 
• 104-55-2 3-phenyl-propenal 
• 591-87-7 Allyl acetate 
• 104-54-1 3-Phenylpropenol 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 670225-01-1 1-[(E)-2-phenylvinyl]but-3-enyl acrylate 
• 6186-91-0 3-chloro-2-fluoropropene 
• 55137-94-5 triallyltin bromide 
• 95978-76-0 allyldiisobutylaluminium 
• 24850-33-7 allyltributylstanane 
• 172925-28-9 trans-(S)-1-phenyl-1,5-hexadien-3-ol 
• 85116-38-7 (+)-diisopinocampheylallylborane 

Downstream Products

• 1174166-09-6 (1R)-1-[(2R,3R)-3-phenyloxiran-2-yl]but-3-en-1-ol 
• 1174166-04-1 (1R)-1-[(2S,3S)-3-phenyloxiran-2-yl]but-3-en-1-ol 
• 639798-55-3 (1R)-1-[(E)-2-phenylvinyl]but-3-enyl acrylate 
• 122046-63-3 (6R)-6-[(2S,3S)-3-phenyloxiran-2-yl]-5,6-dihydro-2H-pyran-2-one 
• 146236-73-9 (+)-goniodiol 

Relevant articles and documents

Photoredox Allylation Reactions Mediated by Bismuth in Aqueous Conditions

Organometallic allylic reagents are widely used in the construction of C?C bonds by Barbier-type reactions. In this communication, we have described a photoredox Barbier allylation of aldehydes mediated by bismuth, in absence of other metals as co-reductants. Mild reaction conditions, tolerance of oxygen, and use of aqueous solvent make this photoredox methodology attractive for green and sustainable synthesis of homoallylic alcohols.

3,3′-Bithiophene-Based Chiral Bisphosphine Oxides as Organocatalysts in Silicon-Derived Lewis Acid Mediated Reactions

This account summarizes the development of new biheteroaromatic chiral bisphosphine oxides. 3,3′-Bithiophene-based phosphine oxides (BITIOPOs) have been successfully used as organocatalysts to promote Lewis base catalyzed, Lewis acid mediated stereoselective transformations. These highly electron-rich compounds, in combination with trichorosilyl derivatives (allyltrichlorosilane and silicon tetrachloride), generate hypervalent silicon species that act as chiral Lewis acids in highly diastereo- and enantioselective organic reactions. Several relevant examples related to these applications are discussed in detail. 1 Introduction 2 The BITIOPO Family 3 Enantioselective Opening of Epoxides 4 Enantioselective Allylation of Aldehydes 5 Stereoselective Direct (Double) Aldol-Type Reaction with Ketones 6 Stereoselective Direct Aldol-Type Reaction with Ester Derivatives 7 Conclusions.

TetraPh-Tol-BITIOPO: A new atropisomeric 3,3′-bithiophene based phosphine oxide as an organocatalyst in Lewis base-catalyzed Lewis acid mediated reactions

A new chiral phosphine oxide based on a 3,3′-bithiophene scaffold (TetraPh-Tol-BITIOPO) was synthesized, fully characterized and separated into antipodes through chiral HPLC. This new compound was successfully employed as an organocatalyst in Lewis base-catalyzed Lewis acid mediated reactions involving trichlorosilyl compounds. The new atropisomeric catalyst was able to promote the allylation of aldehydes with allyltrichlorosilane in up to 98% yield and up to 96% enantiomeric excess (ee), and the direct aldol reaction to afford β-hydroxy ketones and β-hydroxy thioesters, with good chemical yields and modest stereochemical efficiency. Computational studies helped to elucidate and to rationalize the stereochemical outcome of the reactions catalyzed by TetraPh-Tol-BITIOPO that was found to favour the formation of the isomer with an opposite absolute configuration in comparison with the products obtained with the previously reported 3,3′-bithiophene-based catalyst.