22910-59-4

Basic information

• Product Name: (Z)-4-Phenyl-2-buten-1-ol
• Synonyms: (Z)-4-Phenyl-2-buten-1-ol
• CAS NO: 22910-59-4
• Molecular Formula: C₁₀H₁₂O
• Molecular Weight: 0
• Mol File: 22910-59-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (Z)-4-Phenyl-2-buten-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-4-Phenyl-2-buten-1-ol(22910-59-4)
• EPA Substance Registry System: (Z)-4-Phenyl-2-buten-1-ol(22910-59-4)

Safety Data

• Hazardous Substances Data: 22910-59-4(Hazardous Substances Data)

Upstream product

• 930-22-3 epoxybutene 
• 934-56-5 trimethyl(phenyl)stannane 
• 559062-83-8 ethyl (2Z)-4-phenyl-2-butenoate 
• 98-80-6 phenylboronic acid 
• 100-56-1 phenylmercury(II) chloride 
• 507233-69-4 triphenyl bismuth ⁽²⁺⁾; dichloride 
• 37428-55-0 (E)-3-bromoprop-2-en-1-ol 
• 54966-42-6 ethyl 4-phenylbut-2-enoate 
• 300-57-2 allylbenzene 
• 107-18-6 allyl alcohol 
• 122-78-1 phenylacetaldehyde 
• 28495-06-9 4-phenyl-2-butyn-1-ol 
• 6117-80-2 1,4-butenediol 
• 4427-96-7 4-vinyl-1,3-dioxolan-2-one 

Downstream Products

• 132316-73-5 Diazo-acetic acid (Z)-4-phenyl-but-2-enyl ester 
• 161170-91-8 (2R,3S)-2-Hydroxymethyl-3-phenylmethyloxirane 
• 161170-92-9 (2S,3R)-2-Hydroxymethyl-3-phenylmethyloxirane 
• 4392-24-9 (Z)-cinnamyl bromide 
• 260352-20-3 2,2-dimethyl-5-phenyl-4(Z)-pentenal 
• 1535200-75-9 (S,Z)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)-1-(4-(4-phenylbut-2-en-1-yl)piperazin-1-yl)propan-1-one 
• 1535200-80-6 (Z)-1-(4-phenylbut-2-en-1-yl)piperazine 
• 1596359-71-5 (Z)-4′-phenylbut-2′-en-1′-yl (3R,αS,E)-3-[N-benzyl-N-(α-methylbenzyl)amino]hex-4-enoate 
• 78571-81-0 (2S-trans)-3-(Phenylmethyl)oxiranemethanol 
• 78571-81-0 (R,R)-3-(phenylmethyl)oxiranemethanol 
• 78571-81-0 (3-benzyloxiran-2-yl)methanol 
• 154972-23-3 N-((benzyloxy)carbonyl)-2S-amino-1-phenyl-but-3-ene 

Relevant articles and documents

Copper-Catalyzed Aerobic Oxidative Azo-Ene Cyclization

A copper-catalyzed aerobic oxidative azo-ene cyclization has been developed. The developed CuI/DMAP/O2 system efficiently facilitates the aerobic oxidation of ene-containing hydrazides to azo compounds, which undergo azo-ene cyclizations for the synthesis of oxazolidinones. In addition, the present approach enables the synthesis of lactams, as well as a nitroso-ene cyclization. Preliminary mechanistic studies revealed that two carbonyl groups were essential for the successful azo-ene cyclization and that a concerted mechanism might be plausible for this azo-ene cyclization. (Figure presented.).

Transition-Metal-Free Allylic Borylation of 1,3-Dienes

This work explains the reactivity of diboron reagents with 1,3-dienes in a transition-metal-free context. The sole addition of Na2CO3 (30 mol %) to bis(pinacolato)diboron in MeOH allows the 1,4-hydroboration of cyclic and noncyclic 1,3-dienes. The electronic influence on the substrate guarantees the conjugated 1,4-hydroboration versus 1,2-diboration. DFT calculations show that the distribution of charge in the allylic anion intermediate governs the selectivity toward 1,4-hydroboration, while the favored trans configuration in diene reagents determines the preference for the E allyl boronate products.

Copper-Catalyzed Perfluoroalkylation of Allyl Phosphates with Stable Perfluoroalkylzinc Reagents

A general and practical method for copper-catalyzed cross-coupling of allyl phosphates with stable perfluoroalkylzinc reagents has been developed. The reaction proceeds under mild reaction conditions with high efficiency, good functional group tolerance, and high regio- A nd stereoselectivities and provides general, straightforward, and useful access to allyl-perfluoroalkyl compounds. Preliminary mechanistic studies reveal that the allyl copper intermediate may be involved in the catalytic cycle.

Nickel-Catalyzed Direct Coupling of Allylic Alcohols with Organoboron Reagents

The direct coupling of allylic alcohols with arylboronic acids or their derivatives catalyzed by Ni(cod)2 in the presence of a catalytic amount of base has been developed. A wide variety of allylic substrates or arylboronic acids turned out to be applicable to this catalytic system. The present method does not require the use of ligands for stabilizing the nickel catalyst in most cases or additional activators for activation of allylic alcohols.

Stereoretentive Olefin Metathesis Made Easy: In Situ Generation of Highly Selective Ruthenium Catalysts from Commercial Starting Materials

The in situ preparation of highly stereoretentive ruthenium-based metathesis catalysts is reported. This approach completely avoids the isolation of intermediates and air-sensitive catalysts, thus allowing for the rapid access and evaluation of numerous dithiolate Ru catalysts. A procedure was established to perform cross-metathesis reactions without the use of a glovebox, and on a small scale even Schlenk techniques are not required. Consequently, the chemistry displayed in this report is available to every practicing organic chemist and presents a powerful approach for the identification of new stereoretentive catalysts.

Synthesis and Application of Stereoretentive Ruthenium Catalysts on the Basis of the M7 and the Ru-Benzylidene-Oxazinone Design

A series of new stereoretentive ruthenium catalysts bearing the dithiocatecholate ligand was synthesiszed on the basis of the M7 and Ru-benzylidene-oxazinone design. The activity of the catalysts was tested in ring-opening cross-metathesis reactions, ring

Discovery of Benzocycloalkane Derivatives Efficiently Blocking Bacterial Virulence for the Treatment of Methicillin-Resistant S. aureus (MRSA) Infections by Targeting Diapophytoene Desaturase (CrtN)

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High-value alcohols and higher-oxidation-state compounds by catalytic Z-selective cross-metathesis

Olefin metathesis catalysts provide access to molecules that are indispensable to physicians and researchers in the life sciences. A persisting problem, however, is the dearth of chemical transformations that directly generate acyclic Z allylic alcohols, including products that contain a hindered neighbouring substituent or reactive functional units such as a phenol, an aldehyde, or a carboxylic acid. Here we present an electronically modified ruthenium-disulfide catalyst that is effective in generating such high-value compounds by cross-metathesis. The ruthenium complex is prepared from a commercially available precursor and an easily generated air-stable zinc catechothiolate. Transformations typically proceed with 5.0 mole per cent of the complex and an inexpensive reaction partner in 4-8 hours under ambient conditions; products are obtained in up to 80 per cent yield and 98:2 Z:E diastereoselectivity. The use of this catalyst is demonstrated in the synthesis of the naturally occurring anti-tumour agent neopeltolide and in a single-step stereoselective gram-scale conversion of a renewable feedstock (oleic acid) to an anti-fungal agent. In this conversion, the new catalyst promotes cross-metathesis more efficiently than the commonly used dichloro-ruthenium complexes, indicating that its utility may extend beyond Z-selective processes.