Tropinone

Base Information

• Chemical Name: Tropinone
• CAS No.: 532-24-1
• Deprecated CAS: 25866-00-6,35193-79-4,1207071-38-2
• Molecular Formula: C8H13NO
• Molecular Weight: 139.197
• Hs Code.: 29399990
• European Community (EC) Number: 208-530-6
• NSC Number: 118012
• DSSTox Substance ID: DTXSID30862133
• Nikkaji Number: J11.723D
• Wikipedia: Tropinone
• Wikidata: Q104254448
• Mol file: 532-24-1.mol

Synonyms:3-tropinone;3-tropinone hydrobromide;3-tropinone hydrochloride;tropinone

Chemical Property of Tropinone

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.135mmHg at 25°C
• Melting Point: 40-44 °C(lit.)
• Refractive Index: 1.4598 (estimate)
• Boiling Point: 217.1 °C at 760 mmHg
• PKA: 8.93±0.20(Predicted)
• Flash Point: 90 °C
• PSA: 20.31000
• Density: 1.066 g/cm³
• LogP: 0.75000
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 139.099714038
• Heavy Atom Count: 10
• Complexity: 151

Purity/Quality:

99% ^*data from raw suppliers

Tropinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C, Xi
• Hazard Codes: C,Xi
• Statements: 34-22-36/37/38
• Safety Statements: 23-24/25-36/37/39-26-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1C2CCC1CC(=O)C2
• General Description: Tropinone, also known as 3-Tropanone or 8-Methyl-8-azabicyclo[3.2.1]octan-3-one, is a tropane alkaloid derivative that serves as a key intermediate in the synthesis of various pharmacologically active compounds. It is structurally characterized by a bicyclic framework with a ketone group at the 3-position, making it a versatile precursor for modifications, such as demethylation or alkylation, to produce analogs targeting opioid or nociceptin receptors. Its role in medicinal chemistry is highlighted by its use in developing selective ligands for receptors like NOP (nociceptin receptor) or delta opioid receptors, contributing to the design of novel therapeutics with improved selectivity and reduced side effects.

Technology Process of Tropinone

There total 51 articles about Tropinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

cyclohepta-2,6-dienone (1192-93-4) + methylamine hydrochloride (593-51-1) → tropinone (532-24-1)

Guidance literature:

With potassium carbonate; In methanol; at 25 ℃; for 2h;

DOI:10.1021/ja012127+

Reference yield: 55.0%

3-oxo-tropane-2,4-dicarboxylic acid dimethyl ester (100371-46-8) → (+/-)-2-(carbomethoxy)-3-tropinone (36127-17-0) + tropinone (532-24-1)

Guidance literature:

With phosphate buffer; In water; at 20 ℃; for 24h; pH=8.0;

DOI:10.1016/S0040-4039(99)00976-4

Reference yield: 12.0%

(+/-)-hygrine (45771-52-6) → tropinone (532-24-1) + 1-[1-Methyl-pyrrolidin-(2E)-ylidene]-propan-2-one (126412-05-3)

Guidance literature:

With mercury(II) diacetate; In acetic acid; for 18h; Heating;

DOI:10.1039/c39890001899

upstream raw materials:

acetonedicarboxylic acid

butanedial

methylamine hydrochloride

(1-methyl-pyrrolidine-2,5-diyl)-di-acetic acid diethyl ester

Downstream raw materials:

3-oxo-8-azabicyclo[3.2.1]octane-8-carbonitrile

N-methyl-N-phenyl-N'-tropane-3endo-yl-ethylenediamine

N-ethyl-N-phenyl-N'-tropane-3endo-yl-ethylenediamine

N-methyl-N-p-tolyl-N'-tropane-3endo-yl-ethylenediamine

Refernces

Structure-activity relationships of 3-substituted N-benzhydryl-nortropane analogs as nociceptin receptor ligands for the treatment of cough

10.1016/j.bmcl.2008.10.088

The study investigates the structure–activity relationships (SAR) of 3-substituted N-benzhydryl-nortropane analogs as potential nociceptin receptor (NOP) ligands for treating cough. NOP, also known as ORL-1, is an orphan opioid receptor involved in various physiological processes, including cough mediation. The researchers synthesized a series of 3-axial-aminomethyl-N-benzhydryl-nortropane analogs and explored their binding affinity and selectivity for NOP over classic opioid receptors like MOP. Key chemicals involved include tropinone, which was demethylated and alkylated to form a ketone intermediate, and tosylmethyl isocyanide used in the transformation to a nitrile intermediate. The nitriles were further modified to aminomethyl or substituted aminomethyl groups using lithium aluminum hydride (LAH) and other reagents. The synthesized compounds were tested for their binding affinity at the cloned human nociceptin receptor and their functional activities. Compound 18 showed potent NOP binding affinity with a Ki of 6 nM and superior selectivity over MOP binding. Selected compounds demonstrated good DMPK profiles and potent oral antitussive activity in a guinea pig model, with compound 21 showing an ED50 of 0.19 mg/kg at 2 hours. The study highlights the potential of these analogs as novel therapeutic agents for cough management with improved side effect profiles compared to traditional opioid-based antitussives.

4-[(8-Alkyl-8-azabicyclo[3.2.1]octyl-3-yl)-3-arylanilino]-N,N-diethylbenz amides: High affinity, selective ligands for the delta opioid receptor illustrate factors important to antagonist activity

10.1016/S0960-894X(00)00209-2

The study focuses on the synthesis and evaluation of a series of tropane-derived compounds, specifically 4-[(8-alkyl-8-azabicyclo[3.2.1]octyl-3-yl)-3-arylanilino]-N,N-diethylbenzamides (denoted as 5a-d), which were designed to have high affinity and selectivity for the delta opioid receptor. These compounds are structurally similar to the piperidine-based compound 3 and were synthesized to test the hypothesis that limiting conformational flexibility could elicit antagonist activity in nitrogen-transposed compounds similar to 3. The chemicals used in the study include 3-tropanone, 3-methoxyaniline, butylated hydroxyanisole (BHA) ester of 4-fluorobenzoic acid, sodium methoxide, and various reagents for coupling and conversion reactions. The purpose of these chemicals was to synthesize the target compounds and assess their potential as selective ligands for the delta opioid receptor, with the aim of understanding the factors important to antagonist activity and potentially developing new opioid ligands with reduced side effects.

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