7152-32-1

Basic information

• Product Name: 4-cyclohexyl-3-buten-2-one
• Synonyms: 4-cyclohexyl-3-buten-2-one;1-Cyclohexyl-1-butene-3-one;(E)-4-cyclohexylbut-3-en-2-one
• CAS NO: 7152-32-1
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23344
• EINECS: 230-495-0
• Mol File: 7152-32-1.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 236.1°C at 760 mmHg
• Flash Point: 94°C
• Appearance: /
• Density: 0.976g/cm³
• Vapor Pressure: 0.0482mmHg at 25°C
• Refractive Index: 1.528
• CAS DataBase Reference: 4-cyclohexyl-3-buten-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-cyclohexyl-3-buten-2-one(7152-32-1)
• EPA Substance Registry System: 4-cyclohexyl-3-buten-2-one(7152-32-1)

Safety Data

• Hazardous Substances Data: 7152-32-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 92, p. 3503, 1970 DOI: 10.1021/ja00714a066

InChI:InChI=1/C10H16O/c1-9(11)7-8-10-5-3-2-4-6-10/h7-8,10H,2-6H2,1H3/b8-7+

Upstream product

• 2316-84-9 4-cyclohexyl-4-hydroxybutan-2-one 
• 144-62-7 oxalic acid 
• 1809-59-2 1-diethylamino-1-buten-3-one 
• 931-50-0 cyclohexylmagnesium bromide 
• 67-64-1 acetone 
• 2043-61-0 cyclohexanecarbaldehyde 
• 626-62-0 Cyclohexyl iodide 
• 78-94-4 methyl vinyl ketone 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 

Downstream Products

• 861618-55-5 3,5-dioxo-bicyclohexyl-2-carboxylic acid ethyl ester 
• 21527-61-7 4-cyclohexylidene-2-butanone 
• 4484-35-9 3-cyclohexylacrylic acid 
• 17844-66-5 [1,1'-bi(cyclohexane)]-3,5-dione 
• 91763-68-7 5-Cyclohexyl-3-methyl-pent-4-en-1-in-3-ol 
• 868136-07-6 C₁₁H₁₇F₃O₃S 
• 868136-06-5 C₂₄H₃₆O₆ 
• 868136-08-7 UTKO₂ 
• 2316-85-0 4-cyclohexyl-2-butanone 
• 1622486-76-3 3-(1-cyclohexyl-3-oxobutyl)-4-hydroxy-2H-chromen-2-one 

Relevant articles and documents

Overcoming Kinetic and Thermodynamic Challenges of Classic Cope Rearrangements

Systematic evaluation of 1,5-dienes bearing 3,3-electron-withdrawing groups and 4-methylation results in the discovery of a Cope rearrangement for Meldrum's acid-containing substrates that have unexpectedly favorable kinetic and thermodynamic profiles. The protocol is quite general due to a concise and convergent synthesis from abundant starting materials. Furthermore, products with an embedded Meldrum's acid moiety are prepared, which, in turn, can yield complex amides under neutral conditions. We have now expanded the scope of the reductive Cope rearrangement, which, via chemoselective reduction, can promote thermodynamically unfavorable [3,3] sigmatropic rearrangements of 3,3-dicyano-1,5-dienes to form reduced Cope rearrangement products. The Cope rearrangement is found to be stereospecific and can yield enantioenriched building blocks when chiral, nonracemic 1,3-disubstituted allylic electrophiles are utilized. We expand further the use of Cope rearrangements for the synthesis of highly valuable building blocks for complex- and drug-like molecular synthesis.

Gram-scale preparation of dialkylideneacetones through Ca(OH)2-catalyzed Claisen-Schmidt condensation in dilute aqueous EtOH

A synthetic method of dialkylideneacetones has been developed. Compared with known protocols, the method employed catalytic Ca(OH)2 as the cheap, mild base catalyst and dilute aqueous EtOH (20%, v/v) as the green and safe solvent. The procedure was easily operated: In most cases, the product could be isolated by a simple filtration, and purified by washing with water. This paper provided experimental details of the reactions, which could be applied in gram-scale synthesis and should be a very reliable and practical protocol to prepare these useful compounds in laboratory and at the industrial level.

Catalysis by metal-organic frameworks: Proline and gold functionalized MOFs for the aldol and three-component coupling reactions

Translation of homogeneous catalysis into heterogeneous catalysis is a promising solution to green and sustainable development in the chemical industry. Recent research has shown that metal-organic frameworks (MOFs) could bridge the gap between homogeneous and heterogeneous catalysis. We successfully prepared for the first time a novel homochiral Zn-containing MOF referred to as CUP-1 based on the mixed linkers of 2-aminoterephthalic acid and l-lactic acid in a one-pot synthesis. The free NH2 group in the homochiral framework of CUP-1, similar to the well known achiral IRMOF-3, is potentially available for undergoing a variety of organic transformations, as demonstrated by choosing the auxiliary chiral l-proline and nano gold to functionalize MOFs with postsynthetic modification and one-pot synthesis strategies. IRMOF-3, CUP-1 and their functionalized samples were in-depth characterized by X-ray diffraction, N2 adsorption-desorption, optical and transmission electron microscopy, infrared spectroscopy, solid state nuclear magnetic resonance, thermogravimetric and differential thermal analysis, and temperature-programmed reduction. l-Proline functionalized IRMOF-3 shows fair to excellent enantioselectivity (up to 98%) in asymmetrical aldol reactions of aldehydes and acetone with higher turnover numbers and catalytic stabilities than the homogeneous counterpart. The gold functionalized CUP-1 catalysts are found to be highly active, stable and reusable for the three-component coupling reactions of aldehydes, alkynes and amines. This work provides general methods to functionalize MOFs with the active ligand and metal nanoparticles for fabrication of highly efficient MOF-based heterogeneous catalysts. This journal is the Partner Organisations 2014.