13173-09-6 Usage
Description
(+/-)-cis-Bicyclo[3.2.0]hept-2-en-6-one, also known as Bicyclo[3.2.0]hept-2-en-6-one, is an organic compound that is widely utilized in various chemical and biological research applications. It is known for its unique structure and reactivity, making it a valuable compound for studying enantioselective Baeyer-Villiger oxidation and other chemical reactions.
Uses
Used in Chemical Research:
(+/-)-cis-Bicyclo[3.2.0]hept-2-en-6-one is used as a substrate for studying enantioselective Baeyer-Villiger oxidation. This reaction is an important process in organic chemistry, as it allows for the selective oxidation of olefins to form esters or lactones with high enantioselectivity.
Used in Synthesis of Chalcone Derivatives:
In the field of organic synthesis, (+/-)-cis-Bicyclo[3.2.0]hept-2-en-6-one is used to synthesize a series of chalcone derivatives by reacting with arylaldehydes. Chalcone derivatives are known for their diverse range of biological activities, including anti-inflammatory, antioxidant, and anticancer properties.
Used in Analyzing Extremophile Enzymes:
(+/-)-cis-Bicyclo[3.2.0]hept-2-en-6-one is also used to analyze the activity of extremophile enzymes, such as monooxygenases and hydrolases, in microorganisms isolated from deep-water petroleum reservoirs and high-temperature environments. These enzymes are of interest due to their ability to function under extreme conditions, which could have potential applications in biotechnology and industrial processes.
Used in Biooxidation Processes:
(+/-)-cis-Bicyclo[3.2.0]hept-2-en-6-one undergoes preparative scale Baeyer-Villiger biooxidation at high concentrations using recombinant Escherichia coli biocatalyst and adsorbent resin. This process involves in situ substrate feeding and product removal, which can be applied in the production of various chemicals and pharmaceuticals.
Check Digit Verification of cas no
The CAS Registry Mumber 13173-09-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,1,7 and 3 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 13173-09:
(7*1)+(6*3)+(5*1)+(4*7)+(3*3)+(2*0)+(1*9)=76
76 % 10 = 6
So 13173-09-6 is a valid CAS Registry Number.
InChI:InChI=1/C7H8O/c8-7-4-5-2-1-3-6(5)7/h1-2,5-6H,3-4H2/t5-,6-/m1/s1
13173-09-6Relevant articles and documents
REDUCTION OF 7-CHLOROBICYCLOHEPT-2-EN-6-ONES CATALYSED BY 3α,20β-HYDROXYSTEROID DEHYDROGENASE
Davies, H. Geoff,Gartenmann, Thomas C. C.,Leaver, Jeff,Roberts, Stanley M.,Turner, Michael K.
, p. 1093 - 1094 (1986)
7,7-Dichlorobicyclohept-2-en-6-one and 7endo-chlorobicyclohept-2-en-6-one are reduced regio-specifically and with high substrate enantioselectivity using a 3α,20β-hydroxysteroid alcohol dehydrogenase.
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Roberts,Gorham
, p. 2278,2282 (1952)
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Thermal rearrangement of 7-methylbicyclo[3.2.0]hept-2-ene: An experimental probe of the extent of orbital symmetry control in the [1,3] sigmatropic rearrangement
Bender, Jared D.,Leber, Phyllis A.,Lirio, Ruel R.,Smith, Randall S.
, p. 5396 - 5402 (2007/10/03)
The gas-phase thermal rearrangement of exo-7-methylbicyclo[3.2.0]hept-2-ene yields almost exclusively 5-methylnorbornene products. Inversion (i) of configuration dominates this [1,3] sigmatropic shift although some retention (r) is also observed. Because the [1,3] migration can only occur suprafacially (s) in this geometrically constrained system, the si/sr ratio of 7 observed for the migration of C7 in exo-7-methylbicyclo[3.2.0]hept-2-ene indicates that the orbital symmetry rules are somewhat permissive for the [1,3] sigmatropic migration of carbon.
BIOCATALYTIC PREPARATION OF BICYCLOHEPTANE DERIVATIVES
Klempier, Norbert,Geymayer, Paul,Stadler, Peter,Faber, Kurt,Griengl, Herfried
, p. 111 - 118 (2007/10/02)
Bicyclohept-2-en-6-ols, central building blocks for the synthesis of chiral cyclobutane and -pentane systems, were prepared with up to >99percent e.e. by lipase catalysed resolution of their acetates, butyrates, or isobutyrates.Substituents at C-7 vicinal to the reaction site reduced both enantioselectivity and reaction rate, whereas variation of the acid moiety showed a smaller influence.Among the lipases tested, those from Pseudomonas sp. were shown to be superior to those from Candida cylindracea, Mucor sp. and porcine pancreas.