56453-88-4

Basic information

• Product Name: (2E)-3-cyclohex-1-en-1-ylprop-2-enoic acid
• CAS NO: 56453-88-4
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.1904
• Mol File: 56453-88-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 311.1°C at 760 mmHg
• Flash Point: 216.1°C
• Density: 1.186g/cm³
• Vapor Pressure: 0.000127mmHg at 25°C
• Refractive Index: 1.611
• CAS DataBase Reference: (2E)-3-cyclohex-1-en-1-ylprop-2-enoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3-cyclohex-1-en-1-ylprop-2-enoic acid(56453-88-4)
• EPA Substance Registry System: (2E)-3-cyclohex-1-en-1-ylprop-2-enoic acid(56453-88-4)

Safety Data

• Hazardous Substances Data: 56453-88-4(Hazardous Substances Data)

Usage

General Description

The chemical (2E)-3-cyclohex-1-en-1-ylprop-2-enoic acid is a compound with the molecular formula C10H14O2. It is classified as a carboxylic acid and contains a cyclohexene ring. (2E)-3-cyclohex-1-en-1-ylprop-2-enoic acid is commonly used in the synthesis of various pharmaceuticals and agrochemicals. Its structural properties make it useful as a building block for organic synthesis, and it has also been studied for its potential therapeutic applications. However, it is important to handle this chemical with caution, as it may pose health hazards if not handled properly.

Upstream product

• 931-49-7 1-ethenylcyclohexene 
• 124-38-9 carbon dioxide 
• 102651-85-4 (E)-3-(cyclohex-1-en-1-yl)acrylaldehyde 
• 54526-84-0 (E)-3-(cyclohex-1-ene)-prop-2-enoic acid methyl ester 
• 102651-82-1 3-(1-Cyclohexen-1-yl)propenal-dimethylhydrazon 
• 27944-89-4 3-(cyclohex-1-en-1-yl)propiolic acid 
• 75567-08-7 (E)-3-(1-cyclohexen-1-yl)-2-propenoic acid ethyl ester 
• 102651-71-8 1-<2-(Dimethylhydrazono)-1-hydroxyethyl>cyclohexancarbonsaeure, Dilithiumsalz 
• 1552-91-6 cyclohexylideneacetic acid 
• 66400-83-7 Cyclohexylidenacetaldehyd-dimethylhydrazon 
• 1713-63-9 cyclohexylideneacetaldehyde 
• 108-94-1 cyclohexanone 
• 28075-50-5 cyclohex-1-en-1-yl trifluoromethane sulfonate 
• 2043-61-0 cyclohexanecarbaldehyde 

Downstream Products

• 183747-92-4 1,1-dimethyl<(2R,6S)-2-<(1E,3Z,5S)-5-hydroxy-1,3-hexadienyl>-6-methyl-1-piperidine>carboxylate 
• 222972-45-4 (1S,2Z)-<1-methyl-5-(trimethylsilyl)-2-penten-4-ynyl>-3-<(2E)-1-cyclohexen-1-yl>-2-propenoate 
• 228247-99-2 (E)-3-Cyclohex-1-enyl-acrylic acid (Z)-1-methyl-6-(tetrahydro-pyran-2-yloxy)-hex-2-en-4-ynyl ester 
• 745021-33-4 (E)-3-Cyclohex-1-enyl-acrylic acid (Z)-(S)-1-methyl-penta-2,4-dienyl ester 
• 518-99-0 himbeline 
• 6879-74-9 himbacine 
• 226912-84-1 (+)-(3R,3aS,4S,4aR,9aR)-decahydro-4-[(E)-2-[5-[3-(trifluoromethy)phenyl]l-2-pyridinyl]ethenyl]-3-methylnaphtho-[2,3-c]furan-1(3H)-one 

Relevant articles and documents

Semireduction of alkynoic acids via a transition metal-free α borylation-protodeborylation sequence

A method for the semi-reduction of alkynoic acids through an α-borylation and subsequent protodeborylation mechanism has been developed. The transition metal-free protocol is achieved through the activation of bis(pinacolato)diboron by an in situ generated carboxylate moiety yielding aryl acrylic acids. Our studies demonstrate an unprecedented dual role for the carboxylate anion that involves the activation of the diboron reagent and a directing effect in the α-borylation.

A short and convenient preparation of (E)-3-(1-cyclohexenyl)-2- propenoic acid using a palladium(II) complex-catalyzed olefination

A convenient, three-step preparation of (E)-3-(1-cyclohexenyl)-2- propenoic acid (1) from cyclohexanone was developed, which exploited the palladium(II) complex-catalyzed olefination of the triflate 3 as a key step.

Total synthesis of (+)-himbacine and (+)-himbeline

Himbacine (1), a complex piperidine alkaloid isolated from the bark of Australian magnolias, is a promising lead in Alzheimer's disease research due to its potent muscarinic receptor antagonist property. We have described here a highly efficient synthetic strategy that resulted in the total synthesis of himbacine (1) in about 10% overall yield and isohimbacine (1a), an unnatural isomer of himbacine, in 18% overall yield. The total synthesis of himbacine was initially approached using an intramolecular Diels-Alder reaction as the key step to generate intermediate 5 followed by a [3 + 2] cycloaddition with nitrone 4 to produce the isoxazolidine derivative 3. Methylation followed by catalytic reduction of 3 gave 12'-hydroxyhimbacine (20), which, upon dehydration, gave isohimbacine (1a) as the sole product. In an alternative approach, an all-encompassing intramolecular Diels-Alder reaction of an appropriately substituted tetraene derivative 31, which bears the entire latent carbon framework and functional group substitution of himbacine, gave the desired advanced tricyclic intermediate 33, which was readily converted to (+)-himbeline (2) and (+)-himbacine (1).