16112-10-0 Usage
Description
1-Acetyl-1-cyclopentene is a cyclic alkene with the molecular formula C7H10O. It is known for its unique chemical properties, such as the ability of its lithium enolate to undergo Brook rearrangement-mediated [3+4] annulation with 3-alkyl-3-haloacryloylsilanes, leading to the formation of tricyclo[5.3.0.01,4]decenone derivatives. Additionally, asymmetric oxidative Heck reactions of 1-acetyl-1-cyclopentene in the presence of a Pd-ligand have been reported.
Uses
1. Used in the Chemical Industry:
1-Acetyl-1-cyclopentene is used as a key intermediate for the synthesis of various complex organic molecules, such as allenylcycloalkanes. Its unique reactivity and ability to undergo specific chemical reactions make it a valuable compound in the synthesis of advanced materials and pharmaceuticals.
2. Used in the Preparation of Allenylcycloalkanes:
1-Acetyl-1-cyclopentene is used as a starting material for the preparation of the following allenylcycloalkanes:
a) 1-Vinylidenyl-2-[4-(trimethylsilyl)-3-butynyl]-cyclopentane
b) 1-Vinylidenyl-2-(3-butynyl)-cyclopentane
These allenylcycloalkanes have potential applications in various fields, including pharmaceuticals, materials science, and chemical research.
3. Used in Research and Development:
1-Acetyl-1-cyclopentene is utilized in research and development for exploring new synthetic routes and reaction mechanisms, particularly in the context of asymmetric oxidative Heck reactions and Brook rearrangement-mediated annulation reactions. Its unique chemical properties make it an interesting compound for scientists to study and develop new methodologies and applications.
Synthesis Reference(s)
The Journal of Organic Chemistry, 44, p. 450, 1979 DOI: 10.1021/jo01317a033Tetrahedron Letters, 15, p. 1623, 1974
Check Digit Verification of cas no
The CAS Registry Mumber 16112-10-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,1,1 and 2 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 16112-10:
(7*1)+(6*6)+(5*1)+(4*1)+(3*2)+(2*1)+(1*0)=60
60 % 10 = 0
So 16112-10-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H10O/c1-6(8)7-4-2-3-5-7/h4H,2-3,5H2,1H3
16112-10-0Relevant articles and documents
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House,H.O. et al.
, p. 2153 - 2157 (1978)
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Substituted cis-hydrindan-4-ones by sequential cycloadditions
Steffen, Sara,Sch?fer, Andreas,Hiersemann, Martin
, p. 3489 - 3504 (2015/11/17)
The synthesis of substituted cis-hydrindan-4-ones is reported. Particular emphasis was placed on the diastereoselective construction of quaternary stereogenic ring carbon atoms. An intermolecular asymmetric Al(III)-promoted (4+2)-cycloaddition served as the principal C/C-connecting tool. Opportunities for the further structural elaboration of the (4+2)-cycloadducts were explored.
Palladium-catalyzed asymmetric alkylation in the synthesis of cyclopentanoid and cycloheptanoid core structures bearing all-carbon quaternary stereocenters
Hong, Allen Y.,Bennett, Nathan B.,Krout, Michael R.,Jensen, Thomas,Harned, Andrew M.,Stoltz, Brian M.
, p. 10234 - 10248 (2012/01/03)
General catalytic asymmetric routes toward cyclopentanoid and cycloheptanoid core structures embedded in numerous natural products have been developed. The central stereoselective transformation in our divergent strategies is the enantioselective decarboxylative alkylation of seven-membered β-ketoesters to form α-quaternary vinylogous esters. Recognition of the unusual reactivity of β-hydroxyketones resulting from the addition of hydride or organometallic reagents enabled divergent access to γ-quaternary acylcyclopentenes through a ring contraction pathway or γ-quaternary cycloheptenones through a carbonyl transposition pathway. Synthetic applications of these compounds were explored through the preparation of mono-, bi-, and tricyclic derivatives that can serve as valuable intermediates for the total synthesis of complex natural products. This work complements our previous work with cyclohexanoid systems.
