700-58-3 | 2-Adamantanone

Packsize	Purity	Availability	Price	Discounted Price
5g	97%	in stock	$6.00	$4.00
10g	97%	in stock	$7.00	$5.00
25g	97%	in stock	$13.00	$9.00
100g	97%	in stock	$30.00	$21.00
500g	97%	in stock	$106.00	$74.00

Description

• Catalog Number: AB47782
• Chemical Name: 2-Adamantanone
• CAS Number: 700-58-3
• Molecular Formula: C10H14O
• Molecular Weight: 150.2176
• MDL Number: MFCD00074737
• SMILES: O=C1C2CC3CC1CC(C2)C3
• NSC Number: 126345

Computed Properties

• Complexity: 177
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 11
• Hydrogen Bond Acceptor Count: 1
• XLogP3: 1.8

Upstream Synthesis Route

2-Adamantanone, also known as 2-Adamantyl methyl ketone, is a versatile compound widely used in various chemical synthesis applications. Its unique molecular structure, containing a rigid adamantane cage with a ketone functional group, offers exceptional stability and reactivity in diverse reactions.One of the key applications of 2-Adamantanone is as a building block in the synthesis of pharmaceuticals and fine chemicals. Its three-dimensional framework provides steric hindrance that can influence the selectivity and efficiency of reactions. In organic synthesis, 2-Adamantanone serves as a valuable starting material for the preparation of complex molecules due to its ability to undergo a range of functional group transformations.Additionally, 2-Adamantanone is utilized as a key intermediate in the production of advanced materials, including polymers, resins, and specialty chemicals. Its unique structure imparts specific properties to the final products, such as enhanced mechanical strength, thermal stability, and chemical resistance.Moreover, 2-Adamantanone plays a crucial role in the development of novel catalysts and ligands for organic transformations. By incorporating this compound into the design of catalyst systems, chemists can achieve higher reaction rates, selectivity, and recyclability in various synthetic processes.Overall, the diverse applications of 2-Adamantanone in chemical synthesis highlight its significance as a valuable building block for creating advanced materials, pharmaceuticals, and catalysts in the field of organic chemistry.

Literature

• Mechanically induced chemiluminescence from polymers incorporating a 1,2-dioxetane unit in the main chain.

  Nature chemistry 20120603

• Cucurbituril adamantanediazirine complexes and consequential carbene chemistry.

  The Journal of organic chemistry 20120601

• N'-(Adamantan-2-yl-idene)thio-phene-2-carbohydrazide.

  Acta crystallographica. Section E, Structure reports online 20111101

• Nickel(II) complexes of tripodal 4N ligands as catalysts for alkane oxidation using m-CPBA as oxidant: ligand stereoelectronic effects on catalysis.

  Dalton transactions (Cambridge, England : 2003) 20111007

• Spring-loading the active site of cytochrome P450cam.

  Metallomics : integrated biometal science 20110401

• Tuning the conversion of cyclohexane into cyclohexanol/one by molecular dioxygen, protons and reducing agents at a single non-porphyrinic iron centre and chemical versatility of the tris(2-pyridylmethyl)amine TPAFe(II)Cl2 complex in mild oxidation chemistry.

  Dalton transactions (Cambridge, England : 2003) 20110107

• Enolates in 3-D: an experimental and computational study of deprotonated 2-adamantanone.

  The Journal of organic chemistry 20100618

• Chemoselective and biomimetic hydroxylation of hydrocarbons by non-heme micro-oxo-bridged diiron(III) catalysts using m-CPBA as oxidant.

  Dalton transactions (Cambridge, England : 2003) 20090714

• Piperidine dispiro-1,2,4-trioxane analogues.

  Bioorganic & medicinal chemistry letters 20081101

• 2-(Tricyclo[3.3.1.1]dec-2-ylamino)ethanol hemihydrate.

  Acta crystallographica. Section E, Structure reports online 20080701

• Novel and efficient method for the allylation of carbonyl compounds and imines using triallylaluminum.

  The Journal of organic chemistry 20060512

• Substrate modulation of the properties and reactivity of the oxy-ferrous and hydroperoxo-ferric intermediates of cytochrome P450cam as shown by cryoreduction-EPR/ENDOR spectroscopy.

  Journal of the American Chemical Society 20050209

• Novel spiroanellated 1,2,4-trioxanes with high in vitro antimalarial activities.

  Bioorganic & medicinal chemistry letters 20050201

• Synthesis of a silene from 1,1-dilithiosilole and 2-adamantanone.

  Journal of the American Chemical Society 20040505

• Substrate modulates compound I formation in peroxide shunt pathway of Pseudomonas putida cytochrome P450(cam).

  Biochemical and biophysical research communications 20040206

• 6-(2-adamantan-2-ylidene-hydroxybenzoxazole)-O-sulfamate: a potent non-steroidal irreversible inhibitor of human steroid sulfatase.

  Bioorganic & medicinal chemistry letters 20031215

• The oxidation of diamond: the geometry and stretching frequency of carbonyl on the (100) surface.

  Journal of the American Chemical Society 20030604

• Reversible C-C bond formation: solid state structure of the aldol-like addition product of adamantanone to a 1,5-diazapentadienyllithium, and its solution state retro-aldol dissociation.

  Chemical communications (Cambridge, England) 20030321

• An adamantanone derivative that is an original modulator of redox processes in the cytochrome P-450 system can serve as an effective remedy against obliterating angiopathy of lower extremities.

  Doklady. Biochemistry and biophysics 20030101

• Solid-state and solution studies of a tetrameric capsule and its guests.

  Angewandte Chemie (International ed. in English) 20021018

• Green chemistry procedure for the synthesis of cyclic ketals from 2-adamantanone as potential cosmetic odourants.

  International journal of cosmetic science 20021001

• Sn-zeolite beta as a heterogeneous chemoselective catalyst for Baeyer-Villiger oxidations.

  Nature 20010726

• Effect of adamantanone derivative possessing anti-HIV properties on the redox processes in the cytochrome P-450 system.

  Doklady. Biochemistry and biophysics 20010101

• Microbial oxidation of adamantanone by Pseudomonas putida carrying the camphor catabolic plasmid.

  Biochemical and biophysical research communications 19920814