28075-51-6

Basic information

• Product Name: 1-(trifluoromethylsulfonyloxy)cycloheptene
• Synonyms: 1-(trifluoromethylsulfonyloxy)cycloheptene
• CAS NO: 28075-51-6
• Molecular Formula: C₈H₁₁F₃O₃S
• Molecular Weight: 244.23
• Mol File: 28075-51-6.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 264.7°Cat760mmHg
• Flash Point: 113.9°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 0.0157mmHg at 25°C
• Refractive Index: 1.448
• CAS DataBase Reference: 1-(trifluoromethylsulfonyloxy)cycloheptene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(trifluoromethylsulfonyloxy)cycloheptene(28075-51-6)
• EPA Substance Registry System: 1-(trifluoromethylsulfonyloxy)cycloheptene(28075-51-6)

Safety Data

• Hazardous Substances Data: 28075-51-6(Hazardous Substances Data)

Usage

Functional groups

Trifluoromethylsulfonyloxy group

Reactivity

Highly reactive

Versatility

Versatile building block in organic synthesis

Applications

Preparation of various organic compounds

Chemical reactions

Useful in additions, eliminations, and substitution reactions

Electron-withdrawing property

Strong electron-withdrawing group

Leaving group property

Strong leaving group

Fields of application

Medicinal chemistry, agrochemical synthesis, materials science, fine chemicals, and pharmaceuticals

Current status

Actively studied and utilized in the field of organic chemistry

InChI:InChI=1/C8H11F3O3S/c9-8(10,11)15(12,13)14-7-5-3-1-2-4-6-7/h5H,1-4,6H2

Upstream product

• 22081-48-7 (cyclohept-1-en-1-yloxy)(trimethyl)silane 
• 7143-01-3 Methanesulfonic anhydride 
• 502-42-1 cycloheptanone 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 108-94-1 cyclohexanone 

Downstream Products

• 32960-45-5 1-(4-methoxyphenyl)cyclohept-1-ene 
• 1289620-59-2 4-(4-cyclohept-1-en-1-ylphenyl)-N-hydroxy-2-methyl-2-(methylsulfonyl)butanamide 
• 1289627-20-8 C₂₄H₃₅NO₅S 
• 25308-75-2 1-Phenylcycloheptene 

Relevant articles and documents

Visible-Light Photoredox Catalyzed Dehydrogenative Synthesis of Allylic Carboxylates from Styrenes

The visible-light photoredox/[Co(III)] cocatalyzed dehydrogenative functionalization of cyclic and acyclic styryl derivatives with carboxylic acids is documented. The methodology enables the chemo- and regioselective allylic functionalization of styryl compounds, leading to allylic carboxylates (32 examples) under stoichiometric acceptorless conditions. Intermolecular as well as intramolecular variants are documented in high yields (up to 82%). A mechanistic rationale is also proposed on the basis of a combined experimental and spectroscopic investigation.

Sequential Suzuki-Miyaura Coupling/Lewis Acid-Catalyzed Cyclization: An Entry to Functionalized Cycloalkane-Fused Naphthalenes

Functionalized angular cycloalkane-fused naphthalenes were prepared using a two-step process involving a Pd-catalyzed Suzuki-Miyaura coupling of aryl pinacol boronates and vinyl triflates followed by a boron trifluoride etherate-catalyzed cycloaromatization.

Cyclic Alkenylsulfonyl Fluorides: Palladium-Catalyzed Synthesis and Functionalization of Compact Multifunctional Reagents

A series of low-molecular-weight, compact, and multifunctional cyclic alkenylsulfonyl fluorides were efficiently prepared from the corresponding alkenyl triflates. Palladium-catalyzed sulfur dioxide insertion using the surrogate reagent DABSO effects sulfinate formation, before trapping with an F electrophile delivers the sulfonyl fluorides. A broad range of functional groups are tolerated, and a correspondingly large collection of derivatization reactions are possible on the products, including substitution at sulfur, conjugate addition, and N-functionalization. Together, these attributes suggest that this method could find new applications in chemical biology.