4169-27-1

Basic information

• Product Name: octahydroquinolin-2(1H)-one
• Synonyms: octahydroquinolin-2(1H)-one
• CAS NO: 4169-27-1
• Molecular Formula: C₉H₁₅NO
• Molecular Weight: 0
• Mol File: 4169-27-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 321.4°Cat760mmHg
• Flash Point: 186.7°C
• Appearance: /
• Density: 1.014g/cm³
• Vapor Pressure: 0.000298mmHg at 25°C
• Refractive Index: 1.482
• CAS DataBase Reference: octahydroquinolin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: octahydroquinolin-2(1H)-one(4169-27-1)
• EPA Substance Registry System: octahydroquinolin-2(1H)-one(4169-27-1)

Safety Data

• Hazardous Substances Data: 4169-27-1(Hazardous Substances Data)

Usage

General Description

Octahydroquinolin-2(1H)-one, also known as 2-quinuclidinone, is a chemical compound with the molecular formula C7H13NO. It is a bicyclic heterocyclic compound featuring a six-membered ring with nitrogen and oxygen atoms. Octahydroquinolin-2(1H)-one is used in the pharmaceutical industry as a building block for the synthesis of various drug molecules due to its versatile reactivity and ability to form complex structures. It is also utilized as a chiral auxiliary in asymmetric synthesis and as a precursor in the production of fine chemicals. Additionally, this compound has been investigated for potential applications in organic chemistry and medicinal chemistry.

InChI:InChI=1/C9H15NO/c11-9-6-5-7-3-1-2-4-8(7)10-9/h7-8H,1-6H2,(H,10,11)

Upstream product

• 39228-29-0 (E)-methyl 2-nitrocinnamate 
• 859819-28-6 3-(2-benzoylamino-cyclohexyl)-propionic acid 
• 10333-11-6 3,4,5,6,7,8-hexahydro-2-quinolinone 
• 108-94-1 cyclohexanone 
• 553-03-7 3,4-dihydro-2(1H)-quinolone 
• 59-31-4 2-hydroxyquinoline 
• 4594-78-9 cyclohexanone-2-propionitrile 
• 64-17-5 ethanol 
• 64-19-7 acetic acid 
• 612-41-9 2-nitrocinnamic acid 

Downstream Products

• 10343-99-4 decahydroquinoline 
• 80828-13-3 (+/-)-(2R,3aS,7aS)-octahydroindole-2-carboxylic acid 
• 80828-13-3 (+/-)-(2S,3aS,7aS)-octahydroindole-2-carboxylic acid 
• 87624-03-1 (4aS,8aS)-3-Chloro-octahydro-quinolin-2-one 
• 859819-28-6 3-(2-benzoylamino-cyclohexyl)-propionic acid 

Relevant articles and documents

Diastereoselective Rhodium-Catalyzed Hydrogenation of 2-Oxindoles and 3,4-Dihydroquinolones

The benzene ring of indolin-2-ones (2-oxindoles) and 3,4-dihydroquinol-2-ones was converted to a saturated cyclohexane ring by hydrogenation in the presence of the rhodium complex Cy(CAAC)Rh(cod)Cl. The stereoselectivity of the process was found to be high with respect to both external substituent R1 within the saturated part of the heterocyclic ring and substituent X on the benzene ring. Twenty-one hexahydroindolin-2(3H)-ones (70-99% yield, dr = 83/17 to >99/1) and twelve octahydro-2(1H)-quinolinones (87-96% yield, dr = 64/36 to >99/1) were obtained with the major diastereoisomer exhibiting the hydrogen atoms in an all-cis arrangement. The high tolerance toward functional groups and the compatibility with existing stereogenic centers are key features of the hydrogenation protocol presented here.

Highly Selective Hydrogenation of Aromatic Ketones and Phenols Enabled by Cyclic (Amino)(alkyl)carbene Rhodium Complexes

Air-stable Rh complexes ligated by strongly σ-donating cyclic (amino)(alkyl)carbenes (CAACs) show unique catalytic activity for the selective hydrogenation of aromatic ketones and phenols by reducing the aryl groups. The use of CAAC ligands is essential for achieving high selectivity and conversion. This method is characterized by its good compatibility with unsaturated ketones, esters, carboxylic acids, amides, and amino acids and is scalable without detriment to its efficiency.

Cyclic amidine analogs as inhibitors of nitric oxide synthase

Disclosed herein are compounds of Formula I STR1 and pharmaceutically acceptable salts thereof which have been found useful in the treatment of nitric oxide synthase mediated diseases and disorders, including neurodegenerative disorders, disorders of gastrointestinal motility and inflammation. These disease and disorders include hypotension, septic shock, toxic shock syndrom, hemodialysis, IL-2 therapy such as in cancer patients, cachexia, immunosuppression such as in transplant therapy, autoimmune and/or inflammatory indications including sunburn or psoriasis and respiratory conditions such as bronchitis, asthma, and acure respiratory distress (ARDS), myocarditis, heart failure, atherosclerosis, arthritis, rheumatoid arthritis, chronic or inflammatory bowel disease, ulcerative colitis, Crohn's disease, systemic lupus erythematosis (SLE), ocular conditions such as ocular hypertension and uveitis, type 1 diabetes, insulin-dependent diabetes mellitus and cystic fibrosis. Compounds of Formula I are also usful in the treatment of hypoxia, hyperbaric oxygen convulsions and toxicity, dementia, Sydenham's chorea, Parkinson's disease, Huntington's disease, amyotrophic lateral sclerosis, mulitple sclerosis, Korsakoff's disease, imbecility related to cerebral vessel disorder, ischemic brain edema, sleeping disorders, schizophrenia, depression, PMS, anxiety, drug addiction, pain, migraine, immune complex disease, as immunosupressive agents and for preventing or reversing tolerance to opiates and diazepines.