25328-90-9

Basic information

• Product Name: (1E)-1-phenylcyclooctene
• CAS NO: 25328-90-9
• Molecular Formula: C₁₄H₁₈
• Molecular Weight: 186.2927
• Mol File: 25328-90-9.mol

Chemical Properties

• Boiling Point: 285.7°C at 760 mmHg
• Flash Point: 123.4°C
• Density: 0.943g/cm³
• Vapor Pressure: 0.00475mmHg at 25°C
• Refractive Index: 1.529
• CAS DataBase Reference: (1E)-1-phenylcyclooctene(CAS DataBase Reference)
• NIST Chemistry Reference: (1E)-1-phenylcyclooctene(25328-90-9)
• EPA Substance Registry System: (1E)-1-phenylcyclooctene(25328-90-9)

Safety Data

• Hazardous Substances Data: 25328-90-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(1E)-1-phenylcyclooctene is utilized as a building block in organic synthesis, providing a foundation for the creation of more complex organic molecules. Its unique structure allows for various chemical reactions to be performed, facilitating the synthesis of a wide range of compounds.
Used in Pharmaceutical Production:
(1E)-1-phenylcyclooctene serves as a starting material for the production of pharmaceuticals. Its structural properties make it suitable for the development of new drugs, potentially leading to advancements in medicine and healthcare.
Used in Agrochemical Production:
(1E)-1-phenylcyclooctene also finds application in the agrochemical industry, where it is used as a starting material for the synthesis of various agrochemicals. Its role in this industry is crucial for the development of new products that can improve agricultural practices and crop protection.
Used in Specialty Chemicals:
(1E)-1-phenylcyclooctene is employed in the production of specialty chemicals, which are often used in niche applications across different industries. Its unique properties contribute to the development of innovative and specialized chemical products.

Upstream product

• 931-88-4 cis-Cyclooctene 
• 71-43-2 benzene 
• 502-49-8 cycloactanone 
• 108-86-1 bromobenzene 
• 448211-45-8 2-(cyclooct-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 17497-54-0 1-iodo-cyclooctene 
• 603-33-8 triphenylbismuthane 
• 17763-67-6 Phenyl triflate 
• 931-88-4 1,2-cyclooctene 
• 108-95-2 phenol 
• 789-25-3 HSiPh₃ 
• 100-58-3 phenylmagnesium bromide 
• 7287-06-1 1-phenyl-1-cyclooctanol 

Downstream Products

• 16538-85-5 phenylcyclooctane 
• 14996-79-3 2-phenylcyclooctan-1-one 
• 100883-10-1 (Z)-2-phenylcyclooct-2-enone 
• 24314-23-6 8-oxo-8-phenyloctanoic acid 
• 39755-15-2 8-oxo-8-phenyloctanenitrile 
• 29304-32-3 8-oxo-8-phenyloctanal 

Relevant articles and documents

Iodobenzene-catalyzed oxidative cleavage of olefins to carbonyl compounds

A metal-free approach for the oxidative cleavage of carbon–carbon double bonds of olefins to carbonyl compounds was established by using oxidant m-CPBA and non-metallic organocatalyst PhI in toluene/H2O. A broad scope of aromatic olefins was used. All the reactions proceeded smoothly at 35 °C in short reaction time to furnish the respective mono- and double carbonyl compounds selectively in moderate to good yields.

Bimolecular vinylation of arenes by vinyl cations

Styrene derivatives can be easily synthesized from vinyl triflates and arenes under mild reaction conditions, using [Li][Al(OC(CF3)3)4] as a catalyst and LiHMDS as a base. This transformation is likely to involve a vinyl cation intermediate as an electrophile, which is corroborated by DFT calculations, deuterium-labeling and other control experiments. The use of an inert weakly coordinating anion is a decisive factor in this bimolecular vinylation process. This journal is

Triphosgene and DMAP as Mild Reagents for Chemoselective Dehydration of Tertiary Alcohols

The utility of triphosgene and DMAP as mild reagents for chemoselective dehydration of tertiary alcohols is reported. Performed in dichloromethane at room temperature, this reaction is readily tolerated by a broad scope of substrates, yielding alkenes preferentially with the (E)-geometry. While formation of the Hofmann products is generally favored, a dramatic change in alkene selectivity toward the Zaitzev products is observed when the reaction is carried out in dichloroethane at reflux.

Conversion of Carbonyl Compounds to Olefins via Enolate Intermediate

A general and efficient protocol to synthesize substituted olefins from carbonyl compounds via nickel catalyzed C—O activation of enolates was developed. Besides ketones, aldehydes were also suitable substrates for the presented catalytic system to produce di- or tri- substituted olefins. It is worth noting that this approach exhibited good tolerance to highly reactive tertiary alcohols, which could not survive in other reported routes for converting carbonyl compounds to olefins. This method also showed good regio- and stereo-selectivity for olefin products. Preliminary mechanistic studies indicated that the reaction was accomplished through nickel catalyzed C—O activation of enolates, thus offering helpful contribution to current enol chemistry.

Efficient functionalization of olefins by arylsilanes catalyzed by palladium anionic complexes

The coupling of organosilanes and different olefins was performed efficiently in the presence of anionic complexes, [CA]2[PdX4] and [CA]2[Pd2X6], where CA?=?imidazolium or pyridinium cation. The reaction proceeds according to a Pd(II)-mediated pathway, and Cu(OAc)2 acts as the re-oxidant of Pd(0) formed during the catalytic process. High product yields were obtained for differently substituted olefins at 80?°C in 4?h. Styrylsilanes reacted in the same conditions giving unsymmetrical 1,3-dienes.

Achieving vinylic selectivity in Mizoroki-heck reaction of cyclic olefins

In Heck reactions of cyclic olefins, the products usually have aryl groups that end up at the allylic and/or homoallylic position. We herein report new selectivity that adds aryl groups to the vinylic position. Cyclic olefins of various ring size worked well. The desired isomers were produced by palladium-hydride-catalyzed isomerization of the initial products. Thus, a specific catalyst must be used so that it can perform two jobs under one set of reaction conditions. Copyright

Rhodium-catalyzed dehydrogenative borylation of cyclic alkenes

A rhodium-catalyzed dehydrogenative borylation of cyclic alkenes is described. This reaction provides direct access to cyclic 1-alkenylboronic acid pinacol esters, useful intermediates in organic synthesis. Suzuki-Miyaura cross-coupling applications are also presented. The Royal Society of Chemistry 2010.

Atom-efficient vinylic arylations with triarylbismuths as substoichiometric multicoupling reagents under palladium catalysis

The first atom-efficient arylation of vinylic iodides was achieved by using triarylbismuths as substoichiometric multicoupling reagents under palladium catalysis. Vinylic iodides were efficiently coupled with electronically divergent triarylbismuths to furnish the corresponding arylated products in short reaction times.

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