768-00-3

Usage

Uses

Used in Chemical Synthesis:
cis-2-Phenyl-2-butene is used as a synthetic intermediate for the production of various organic compounds. Its unique structure allows it to be a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
cis-2-Phenyl-2-butene is used as a key component in the development of new drugs. Its specific configuration and reactivity make it a valuable candidate for the creation of novel therapeutic agents with potential applications in treating various diseases and medical conditions.
Used in Research and Development:
cis-2-Phenyl-2-butene is employed as a reactant in the study of asymmetric hydrogenations of minimally functionalized olefins. This research is crucial for understanding the catalytic properties of iridium-containing complexes and their potential applications in the synthesis of enantiomerically pure compounds, which are essential in the pharmaceutical and agrochemical industries.
Used in Material Science:
cis-2-Phenyl-2-butene can be utilized in the development of new materials with specific properties, such as improved mechanical strength, thermal stability, or chemical resistance. Its unique molecular structure can be exploited to create novel polymers, coatings, or composites with tailored characteristics for various applications.

InChI:InChI=1/C10H12/c1-3-9(2)10-7-5-4-6-8-10/h3-8H,1-2H3/b9-3+

Upstream product

• 4894-61-5 trans-but-2-enyl chloride 
• 2173-69-5 2-methyl-2-phenyl-propan-1-ol 
• 135-98-8 sec-Butylbenzene 
• 10467-10-4 ethylmagnesium iodide 
• 98-86-2 acetophenone 
• 925-90-6 ethylmagnesium bromide 
• 51380-79-1 β-phenylisovaleryl p-nitrobenzoyl peroxide 
• 62726-47-0 β-phenylisovaleryl peroxide 
• 87931-48-4 3-phenyl-pent-3-enoic acid 
• 4091-39-8 3-chloro-2-butanone 
• 591-51-5 phenyllithium 
• 1530-32-1 ethyltriphenylphosphonium bromide 
• 100-42-5 styrene 
• 74-85-1 ethene 

Downstream Products

• 4564-81-2 1-phenyl-1,2-dimethyloxirane 
• 59341-61-6 3-phenylselenophene 
• 824-90-8 1-phenylbut-1-ene 
• 104-51-8 1-butylbenzene 
• 135-98-8 sec-Butylbenzene 
• 13633-25-5 1-Bromo-4-phenylbutane 
• 143097-80-7 2-bromo-4-phenylbutane 
• 52392-57-1 2-bromo-3-phenyl-but-2c-ene 
• 52392-58-2 2-bromo-3-phenyl-but-2t-ene 
• 2404-87-7 3-phenylthiophene 
• 860687-81-6 (1,2-dibromo-1-methyl-propyl)-benzene 
• 65674-14-8 1,2-dibromo-4-phenylbutane 
• 52427-18-6 (+/-)-4-Hydroxy-1-(1-methyl-1-phenyl-propyl)-benzol 
• 40527-60-4 3-Brom-2-methyl-1,1,1-trinitro-2-phenyl-butan 

Relevant academic research and scientific papers

Modular Ni(0)/Silane Catalytic System for the Isomerization of Alkenes

Alkenes are used ubiquitously as starting materials and synthetic targets in all areas of chemistry. Controlling their geometry and position along a chain is vital to their reactivity and properties yet remains challenging. Alkene isomerization is an atom-economical process to synthesize targeted alkenes, and selectivity can be controlled using transition metal catalysts. The development of mild, selective isomerization reactivity has enabled efficient tandem catalytic systems for the remote functionalization of alkenes, a process in which a starting alkene is isomerized to a new position prior to the functionalization step. The key challenges in developing isomerization catalysts for remote functionalization applications are (i) a lack of modularity in the catalyst structure and (ii) the requirement of nonmodular and/or harsh additives during catalyst activation. We address both challenges with a modular (NHC)Ni(0)/silane catalytic system (NHC, N-heterocyclic carbene), demonstrating the use of triaryl silanes and readily accessible (NHC)Ni(0) complexes to form the proposed active (NHC)(silyl)Ni-H species in situ. We show that modification of the steric and electronic nature of the catalyst via modification of the ancillary ligand and silane partner, respectively, is easily achieved, creating a uniquely versatile catalytic system that is effective for the formation of internal alkenes with high yield and selectivity for the E-alkene. The use of silanes as mild activators enables isomerization of substrates with a variety of functional groups, including acid-labile groups. The broad substrate scope, enabled by catalyst design, makes this catalytic system a strong candidate for use in tandem catalytic applications. Preliminary mechanistic studies support a Ni-H insertion/elimination pathway.

Method for synthesizing 1, 2-disubstituted olefin through reaction of terminal group olefin and sulfoxide

The invention discloses a method for synthesizing 1, 2-disubstituted olefin by reaction of terminal olefin and sulfoxide. According to the method, terminal olefin with sulfoxide make reaction in one pot in the presence of ferric salt and hydrogen peroxide to generate the 1, 2-disubstituted olefin. sulfoxide is simultaneously used as a hydrocarbylation reagent and a solvent of olefin, and a reaction product is 1, 2-disubstituted olefin of which a terminal carbon atom in terminal olefin is coupled with a sulfoxide alkyl group, so that an olefin carbon chain is increased; the reaction conditionsare mild, the selectivity is high, the yield is high, and industrial production is facilitated.

Regioselective Three-Component Synthesis of Vicinal Diamines via 1,2-Diamination of Styrenes

The vicinal diamine motif plays a significant role in natural products, drug design, and organic synthesis, and development of synthetic methods for the synthesis of diamines is a long-standing interest. Herein, we report a regioselective intermolecular three-component vicinal diamination of styrenes with acetonitrile and azodicarboxylates. The diamination products can be produced in moderate to excellent yields via the Ritter reaction. Synthetic applications and theoretical studies of this reaction have been conducted.

Mono-Gold(I)-Catalyzed Enantioselective Intermolecular Reaction of Ynones with Styrenes: Tandem Diels–Alder and Ene Sequence

Gold-catalyzed intermolecular reaction leading to dihydronaphthalene derivatives in one pot from two equivalents of ynones with respect to styrene is uncovered. The [4+2] Diels–Alder cycloaddition of ynones and styrenes is catalyzed by a mono-gold(I) complex and the conjugated acid to provide an unstable 3,8a-dihydronaphthalene to subsequently undergo an intermolecular ene-type reaction with the π-activated ynone to afford multi-component coupling dihydronaphthalene products. Linear relationships between chiral ligand-gold complexes and chiral dihydronaphthalene products proves mono-gold catalysis that triggers an asymmetric tandem Diels–Alder and ene reaction sequence.

Visible-Light-Induced Meerwein Fluoroarylation of Styrenes

An unprecedented approach for assembling a broad range of 1,2-diarylethane derivatives with fluorine-containing fully substituted carbon centers was developed. The protocol features straightforward operation, proceeds under metal-free condition, and accommodates a large variety of synthetically useful functionalities. The critical aspect to the success of this novel transformation lies in using aryldiazonium salts as both aryl radical progenitor and also as single electron acceptor which elegantly enables a radical-polar crossover manifold.

Palladium-Catalyzed Markovnikov Hydroaminocarbonylation of 1,1-Disubstituted and 1,1,2-Trisubstituted Alkenes for Formation of Amides with Quaternary Carbon

Hydroaminocarbonylation of alkenes is one of the most promising yet challenging methods for the synthesis of amides. Herein, we reported the development of a novel and effective Pd-catalyzed Markovnikov hydroaminocarbonylation of 1,1-disubstituted or 1,1,2-trisubstituted alkenes with aniline hydrochloride salts to afford amides bearing an α quaternary carbon. The reaction makes use of readily available starting materials, tolerates a wide range of functional groups, and provides a facile and straightforward approach to a diverse array of amides bearing an α quaternary carbon. Mechanistic investigations suggested that the reaction proceeded through a palladium hydride pathway. The hydropalladation and CO insertion are reversible, and the aminolysis is probably the rate-limiting step.

The effects of using an ionic liquid as a solvent for a reaction that proceeds through a phenonium ion

A unimolecular reaction that proceeds predominantly through a phenonium ion intermediate was investigated in mixtures of an ionic liquid and methanol. Varying the proportion of the ionic liquid in the reaction mixture led to an increase in the rate constant compared with methanol when very small amounts of ionic liquid were present in the reaction mixture and a decrease when higher proportions of the salt were present. Activation parameters determined for the process showed that the effect of changing the solvent composition on the rate constant was due to a key interaction between the ionic liquid and the transition state of the process, similar to other unimolecular processes. Analysis of the stereochemistry of the products demonstrated that the ionic liquid had no effect on either the ratio of the stereochemistry of the substitution products, or the ratio of the substitution and eliminations mechanisms occurring in solution.

Highly Stereoselective Positional Isomerization of Styrenes via Acid-Catalyzed Carbocation Mechanism

The first transition metal-free highly stereoselective positional isomerization of various α-alkyl styrenes through a carbocation mechanism triggered strategy is developed by using Al(OTf)3 as a hidden Br?nsted acid catalyst, which provides facile access to value-added acyclic tri- and tetra-substituted alkenes in good yields with high stereoselectivity under mild conditions. The practicality of this protocol is further highlighted by the gram-scale synthesis, high stereoselectivity, good functional group tolerance, and simple operation. Mechanistic studies support that Al(OTf)3 acts as a hidden Br?nsted acid catalyst and a carbocation intermediate is formed.

Iron Catalyzed Isomerization of α-Alkyl Styrenes to Access Trisubstituted Alkenes

Stereoselective isomerization of α-alkyl styrenes is accomplished using a new iron catalyst supported by phosphine-pyridine-oxazoline (PPO) ligand. The protocol provides an atom-efficient and operationally simple approach to trisubstituted alkenes in high

Method for stereoselective synthesis of (E)-trisubstituted olefin

Belonging to the technical field of metal catalytic synthesis, the invention discloses a method for stereoselective synthesis of (E)-trisubstituted olefin. The method includes: taking 1, 1-disubstituted olefin as the raw material, and adopting a combination of CoX2 and PAO ligand as the catalyst; and in the presence of an activating reagent, carrying out reaction for 0.5min-48h at a temperature ranging from -30DEG C to 80DEG C to prepare (E)-trisubstituted olefin. Compared with the prior art, the method has the advantages of more economical, efficient and environment-friendly catalyst, good tolerance of the reaction functional group, mild reaction conditions, simple operation, no need for participation of additional reagents, and atom economy of 100%. In addition, the reaction has no needof any other toxic transition metal (like ruthenium, rhodium, palladium, etc.) salt, therefore the method has great practical application value in pharmaceutical and food chemical industry.