122332-14-3

Basic information

• Product Name: (S)-1-phenylpent-4-en-2-ol
• Synonyms: (S)-1-phenylpent-4-en-2-ol
• CAS NO: 122332-14-3
• Molecular Weight: 162.232
• Mol File: 122332-14-3.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (S)-1-phenylpent-4-en-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-phenylpent-4-en-2-ol(122332-14-3)
• EPA Substance Registry System: (S)-1-phenylpent-4-en-2-ol(122332-14-3)

Safety Data

• Hazardous Substances Data: 122332-14-3(Hazardous Substances Data)

Upstream product

• 6566-38-7 cis-1,2-dihydroxy-1,2-dimethyl-1,2-dihydroacenaphthalene 
• 28557-00-8 phenylzinc chloride 
• 591-51-5 phenyllithium 
• 106-95-6 allyl bromide 
• 74-88-4 methyl iodide 
• 122-78-1 phenylacetaldehyde 
• 1097189-44-0 allyl(dimethyl)(2-phenylethanoyl)silane 
• 1097189-54-2 2-(allyldimethylsilyl)-2-benzyl-1,3-dithiane 
• 31593-52-9 2-benzyl-1,3-dithiane 
• 1730-25-2 allylmagnesium bromide 
• 107-37-9 allyltrichlorosilane 
• 108-22-5 Isopropenyl acetate 

Downstream Products

• 1150312-95-0 (4R)-5-phenylpentane-1,2,4-triol 
• 1351823-05-6 (S)-4-(tert-butoxycarbonyloxy)-5-phenylpent-1-ene 
• 1351823-03-4 (S)-4-(tert-butyldimethylsiloxy)-5-phenylpent-1-ene 
• 1351823-10-3 (S)-4-(tert-butyldiphenylsiloxy)-5-phenylpent-1-ene 
• 1351823-09-0 (2R,4R)-4-(tert-butyldiphenylsiloxy)-5-phenylpentane-1,2-diol 
• 1351823-11-4 (R)-2-(tert-butyldiphenylsiloxy)-1-(oxiran-2-yl)-3-phenylpropane 
• 1351823-04-5 (2R,4R)-4-(tert-butyldimethylsiloxy)-5-phenylpentane-1,2-diol 
• 1351823-02-3 (2R,4R)-4-(tert-butyldimethylsiloxy)-5-phenylpentane-1,2-diol 
• 1351823-06-7 (4R,6R)-4-benzyl-6-(iodomethyl)-1,3-dioxan-2-one 
• 1351823-07-8 (R)-1-[(R)-oxiran-2-yl]-3-phenylpropan-2-ol 
• 1351823-08-9 (R)-2-(tert-butyldiphenylsiloxy)-1-[(R)-oxiran-2-yl]-3-phenyl-propane 
• 203243-30-5 3-hydroxy-5-phenylmethyl-(3R,5R)-tetrahydrofuran-2-one 
• 1374151-64-0 2-benzyl-4-hydroxy-1-oxa-7-azacyclotetradecane-6,14-dione 
• 1374151-65-1 C₁₉H₂₉NO₅ 

Relevant articles and documents

An evolutionary model encompassing substrate specificity and reactivity of type i polyketide synthase thioesterases

Bacterial polyketides are a rich source of chemical diversity and pharmaceutical agents. Understanding the biochemical basis for their biosynthesis and the evolutionary driving force leading to this diversity is essential to take advantage of the enzymes as biocatalysts and to access new chemical diversity for drug discovery. Biochemical characterization of the thioesterase (TE) responsible for 6-deoxyerythronolide macrocyclization shows that a small, evolutionarily accessible change to the substrate can increase the chemical diversity of products, including macrodiolide formation. We propose an evolutionary model in which TEs are by nature non-selective for the type of chemistry they catalyze, producing a range of metabolites. As one metabolite becomes essential for improving fitness in a particular environment, the TE evolves to enrich for that corresponding reactivity. This hypothesis is supported by our phylogenetic analysis, showing convergent evolution of macrodiolide-forming TEs.

Enantioselective 1,2-Anionotropic Rearrangement of Acylsilane through a Bisguanidinium Silicate Ion Pair

Highly enantioselective bisguanidinium-catalyzed tandem rearrangements of acylsilanes are reported. The acylsilanes were activated via an addition of fluoride on the silicon to form a penta-coordinate anionic silicate intermediate. The silicate then underwent alkyl or aryl group migration from the silicon atom to the neighboring carbonyl carbon atom (1,2-anionotropic rearrangement), followed by [1,2]-Brook rearrangement to provide the secondary alcohols in high yields with excellent enantioselectivities (up to 95% ee). The isolation of an α-silylcarbinol intermediate as well as DFT calculations revealed that the 1,2-anionotropic rearrangement occurred via a bisguanidinium silicate ion pair, which is the stereodetermining step. The chiral center formed is then retained without inversion through the subsequent [1,2]-Brook rearrangement. Crotyl acylsilanes were smoothly transformed into homoallylic linear crotyl alcohols with retention of E/Z geometry, and no branched alcohols were detected. This clearly suggested that the 1,2-anionotropic rearrangement occurred through a three-membered instead of a five-membered transition state.

Towards a characterization of the structural determinants of specificity in the macrocyclizing thioesterase for deoxyerythronolide B biosynthesis

Type I polyketide synthases (PKSs) are giant multidomain proteins that synthesize many therapeutics and other natural products. The synthesis proceeds by a thiotemplate mechanism whereby intermediates are covalently attached to the PKS. The release of the final polyketide is catalyzed by the terminal thioesterase (TE) domain through hydrolysis, transesterification, or macrocyclization. The PKS 6-deoxyerythronolide B synthase (DEBS) produces the 14-membered macrolide core of the clinically important antibiotic erythromycin. The TE domain of DEBS (DEBS TE) has well-established, empirically-defined specificities for hydrolysis or macrocyclization of native and modified substrates. We present efforts towards understanding the structural basis for the specificity of the thioesterase reaction in DEBS TE using a set of novel diphenyl alkylphosphonates, which mimic substrates that are specifically cyclized or hydrolyzed by DEBS TE. We have determined structures of a new construct of DEBS TE alone at 1.7 ?, and DEBS TE bound with a simple allylphosphonate at 2.1 ? resolution. Other, more complex diphenyl alkylphosphonates inhibit DEBS TE, but we were unable to visualize these faithful cyclization analogs in complex with DEBS TE. This work represents a first step towards using DEBS TE complexed with sophisticated substrate analogs to decipher the specificity determinants in this important reaction.