512-16-3 Usage
Uses
Used in Pharmaceutical Industry:
Cyclobutyrol is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with specific therapeutic properties, making it a valuable component in the design and production of novel medications.
Used in Chemical Synthesis:
Cyclobutyrol serves as a key building block in the synthesis of complex organic molecules. Its cyclohexane ring and functional groups make it a versatile starting material for the creation of a wide range of chemical products, including specialty chemicals and advanced materials.
Used in Research and Development:
Due to its unique structure and properties, cyclobutyrol is used as a research compound in various scientific studies. It can be employed to investigate the properties of cyclohexane derivatives, explore new synthetic pathways, and develop innovative applications in various fields, such as materials science, pharmaceuticals, and biotechnology.
Originator
Hebucol,Logeais,France,1957
Manufacturing Process
Into a balloon flask with two lateral necks furnished with an efficient
mechanical agitator and protected from moisture by a calcium chloride guard,
there are introduced 12 g (0.185 mol) of pure powdered zinc and 20 ml of a
solution of 16.6 g (0.17 mol) of anhydrous cyclohexanone and 31.5 g (0.16
mol) of ethyl α-bromobutyrate in 25 ml of anhydrous benzene. With vigorous
stirring in a manner to put the zinc into suspension, the balloon flask is
gradually heated in an oil bath to 100°C to 105°C. After a few minutes, a
reaction starts, causing violent boiling which is maintained while adding the
balance of the reactants. Boiling is then continued for one hour. After cooling,
the reaction mixture is turned into a beaker containing 30 ml of sulfuric acid
to half (by volume) with ice. After agitation, the mixture is decanted into a
container for separation. The aqueous phase is reextracted with benzene. The
pooled benzene solutions are washed with dilute (10%) cold sulfuric acid, then
with cold sodium carbonate (5%) and then with ice water, and dried over
anhydrous sodium sulfate. The benzene is evaporated and the ester, which is
ethyl α(hydroxy-1-cyclohexyl) butyrate, is distilled off under reduced pressure.
The yield obtained was 17 to 19 g or 49% to 55%.The ester was saponified with baryta in aqueous methanol as follows:21.5 g (0.1 mol) of the above ethyl ester is saponified by boiling under reflux
for 4 hours, while agitating, with 30 g (0.095 mol) of barium oxide hydrated
to 8H2O in 250 ml of a mixture of equal volumes of methanol and water. After
concentration to one-half its volume under reduced pressure and filtration, the
aqueous solution is washed with ether and then acidified at 0°C with 10%
hydrochloric acid. The acid liberated in oily form is extracted with ether. The
ether is washed with water, dried and evaporated. The yield is 75-80% (14-15
g of crude acid) which crystallizes spontaneously little by little. It can be
crystallized in a mixture of ether and petroleum ether (1:10) or, with better
yield, in light gasoline or oil (solubility of the pure acid ranges from 0.3% at
0°C to 100% at the boiling point). The yield of crystals is 75-80%. The
α(hydroxy-1-cyclohexyl) butyric acid thus obtained is a colorless crystalline
product with a melting point of 81°C to 82°C.
Therapeutic Function
Choleretic
Check Digit Verification of cas no
The CAS Registry Mumber 512-16-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 2 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 512-16:
(5*5)+(4*1)+(3*2)+(2*1)+(1*6)=43
43 % 10 = 3
So 512-16-3 is a valid CAS Registry Number.
InChI:InChI=1/C10H18O3/c1-2-8(9(11)12)10(13)6-4-3-5-7-10/h8,13H,2-7H2,1H3,(H,11,12)
512-16-3Relevant academic research and scientific papers
Synthesis and biological evaluation of cycloalkylidene carboxylic acids as novel effectors of Ras/Raf interaction
Friese, Anke,Hell-Momeni, Katja,Zündorf, Ilse,Winckler, Thomas,Dingermann, Theodor,Dannhardt, Gerd
, p. 1535 - 1542 (2007/10/03)
The protooncogenes Ras and Raf play important roles in signal transduction pathways regulated by mitogen-activated protein kinases. Mutations of Ras that arrest the protein in its active state are frequently implicated in tumor formation. We used Ras and Raf proteins in the yeast two-hybrid system to search for natural or synthesized substances capable of modulating Ras/Raf interaction by specifically binding to one of the interacting partners. We found that cycloalkylidene carboxylic acids enhanced Ras/Raf interaction by acting on the cysteine-rich domain of Raf. Several analogues of the active substance 2-cyclohexylidene propanoic acid were synthesized and the importance of the semicyclic double bond in the stabilization of Ras/Raf interaction was demonstrated. Variation of the size and the substituents of the cyclic system as well as the length of the carboxylic acid resulted in enhanced Ras/Raf interaction.
SYNTHETIS OF CYCLIC AND ACYCLIC β,γ-UNSATURATED CARBOXYLIC ACIDS VIA AN E1-TYPE IONIZATION/ELIMINATION OF β-LACTONES
Black, T. Howard,Eisenbeis, Shane A.,McDermott, Todd S.,Maluleka, Stephen L.
, p. 2307 - 2316 (2007/10/02)
Cyclic and acyclic ketones were converted in three steps into 3-alkenoic acids, bearing a variety of substituents in the α-position.The sequence, involving ionization/elimination of a β-lactone, affords high yields of pure products uncontaminated with conjugated isomers.Support for an E1-type mechanism is also provided.
A NOVEL SYNTHESIS OF MONO- AND DISUBSTITUTED (1-CYCLOALKENYL) ACETIC ACID DERIVATIVES VIA IONIZATION/ELIMINATION OF β-LACTONES
Black, T. Howard,Eisenbeis, Shane
, p. 2243 - 2248 (2007/10/02)
Spiro β-lactones undergo an ionization/elimination reaction to afford cycloalkenyl acetic acid derivatives in high yield and isomeric purity.
