5581-94-2

Basic information

• Product Name: 3-(tert-Butyl)cyclopentanone
• Synonyms: 3-(tert-Butyl)cyclopentanone
• CAS NO: 5581-94-2
• Molecular Formula: C₉H₁₆O
• Molecular Weight: 140
• Mol File: 5581-94-2.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 192.9°Cat760mmHg
• Flash Point: 63.4°C
• Appearance: /
• Density: 0.925g/cm³
• Vapor Pressure: 0.478mmHg at 25°C
• Refractive Index: 1.458
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-(tert-Butyl)cyclopentanone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(tert-Butyl)cyclopentanone(5581-94-2)
• EPA Substance Registry System: 3-(tert-Butyl)cyclopentanone(5581-94-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 5581-94-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 47, p. 3805, 1982 DOI: 10.1021/jo00140a054

InChI:InChI=1/C9H16O/c1-9(2,3)7-4-5-8(10)6-7/h7H,4-6H2,1-3H3

Upstream product

• 10347-88-3 2-tert-butyl-1,4-butanedicarboxylic acid 
• 75-11-6 diiodomethane 
• 20614-90-8 3-(tert-butyl)cyclobutanone 
• 3875-52-3 tert-butylcyclopentane 
• 82491-60-9 dimethyl 2-cyclopentylmalonate 
• 1125-23-1 2-cyclopentyl-2-methylpropane-1,3-diol 
• 930-30-3 cyclopent-2-enone 
• 98-52-2 4-(1,1-dimethylethyl)-cyclohexanol 
• 88828-77-7 1,2-Dimethyl-4-tert.-butyl-cyclohex-1-en 
• 80452-16-0 1,2-dimethyl-4-tert-butylcyclohexanol 
• 7360-39-6 1-acetoxy-4-tert-butylcyclohexene 
• 5064-52-8 2-methyl-4-tert-butylcyclohexanone 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 5682-70-2 3-tert-butyl-2-cyclopenten-1-one 

Downstream Products

• 5469-26-1 1-Bromopinacolon 
• 5682-67-7 2-tert-butylcyclopent-2-en-1-one 

Relevant articles and documents

Cyclization of the 3-tert-Butylhex-5-enyl Radical: A Test of Transition-State Structure

The reaction of either of the radical precursors 5 or 8 with tributylstannane in benzene gives a mixture of open-chain and cyclized products 11 and 12, the ratio of yields of which depends, as expected, on the concentration of stannane.The magnitude of the rate constant for cyclization of the radical 9, kc ca. 2 * 108 s-1 at 80 deg C, reflects the effect of the bulky tert-butyl substituent on the strain energy of the ground state.The ratio of yields of the diastereomers of 12 (cis/trans = 4.5) is independent of stannane concentration.The difference of free energies of activation, ΔG(excit)(trans) - ΔG(excit)(cis) of 1.0 kcal, is in agreement with the theoretical predictions based on the hypothesis that cis cyclization proceeds through a chairlike transition structure 13c while trans cyclization involves a boatlike transition structure 15c.

Deciphering Reactivity and Selectivity Patterns in Aliphatic C-H Bond Oxygenation of Cyclopentane and Cyclohexane Derivatives

A kinetic, product, and computational study on the reactions of the cumyloxyl radical with monosubstituted cyclopentanes and cyclohexanes has been carried out. HAT rates, site-selectivities for C-H bond oxidation, and DFT computations provide quantitative information and theoretical models to explain the observed patterns. Cyclopentanes functionalize predominantly at C-1, and tertiary C-H bond activation barriers decrease on going from methyl- and tert-butylcyclopentane to phenylcyclopentane, in line with the computed C-H BDEs. With cyclohexanes, the relative importance of HAT from C-1 decreases on going from methyl- and phenylcyclohexane to ethyl-, isopropyl-, and tert-butylcyclohexane. Deactivation is also observed at C-2 with site-selectivity that progressively shifts to C-3 and C-4 with increasing substituent steric bulk. The site-selectivities observed in the corresponding oxidations promoted by ethyl(trifluoromethyl)dioxirane support this mechanistic picture. Comparison of these results with those obtained previously for C-H bond azidation and functionalizations promoted by the PINO radical of phenyl and tert-butylcyclohexane, together with new calculations, provides a mechanistic framework for understanding C-H bond functionalization of cycloalkanes. The nature of the HAT reagent, C-H bond strengths, and torsional effects are important determinants of site-selectivity, with the latter effects that play a major role in the reactions of oxygen-centered HAT reagents with monosubstituted cyclohexanes.

Alkyl radical precursor and application thereof in establishing C-C bond

The invention provides a precursor for generating an alkyl radical based on the visible light induction and a novel method for generating the radical. The alkyl sulfenamide is used as the radical precursor to generate the alkyl radical by virtue of the C-S bond cracking accelerated by the visible light, and then the alkyl radical is applied to the chemical reaction for establishing a C-C bond. Thereaction system has the characteristic of high efficiency, and has important scientific significance and application value for researching the novel C-C bond formation reaction, organic synthesis, drug synthesis and the like. In general, the invention provides a novel general method having practical application value. The thioalcohol (thioether) with rich resources is converted to a tool for derivating the alkyl radical.

TREATMENT OF CHAGAS DISEASE

The invention provides compounds of the formula: wherein L1 and L2 are independently selected from O and S; R1 is C3-C6straight or branched alkyl, C3-C7cycloalkyl, C5-C7cycloalkenyl, adamantly, phenyl or saturated heterocyclyl, any of which being optionally substituted; R2 is H, methyl or ethyl; R5 is NRxCORy, NRxRy, CH2COCH3, CH2C≡N, or a 5- or 6-membered heteroaryl group which is optionally substituted; X, Y and Z are independently N or CH; Rx is independently H or C1-C4alkyl; Ry is independently H, CrC4alkyl, phenyl or benzyl, either of which is optionally substituted; n is 0-3; salts, hydrates and N-oxides, wherein the optional substituents are further defined in the claims. The compounds have utility in the prophylaxis or treatment of trypanosomal diseases, such as T. cruzi (Chagas disease).