936-52-7

Usage

Chemical Properties

clear yellow liquid

InChI:InChI=1/C9H15NO/c1-2-4-9(3-1)10-5-7-11-8-6-10/h3H,1-2,4-8H2/p+1

Upstream product

• 110-91-8 morpholine 
• 120-92-3 cyclopentanone 
• 30882-93-0 morpholine-N-carboxylic acid trimethylsilyl ester 
• 142-29-0 cyclopentene 
• 930-29-0 1-chlorocyclopent-1-ene 

Downstream Products

• 18012-77-6 4-(2-phenyl-hexahydro-cyclopenta[b]furan-6a-yl)-morpholine 
• 29942-16-3 1-benzoylsulfanyl-1-morpholin-4-yl-cyclopentane 
• 98222-46-9 3-(4-chloro-phenyl)-6a-morpholin-4-yl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole 
• 16424-38-7 2-Nonyliden-cyclopentanon 
• 66646-17-1 6a-morpholin-4-yl-3-[5-(2-nitro-phenyl)-furan-2-yl]-(3ar,6ac)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole 
• 66646-19-3 6a-morpholin-4-yl-3-[5-(4-nitro-phenyl)-furan-2-yl]-(3ar,6ac)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole 
• 66646-18-2 6a-morpholin-4-yl-3-[5-(3-nitro-phenyl)-furan-2-yl]-(3ar,6ac)-4,5,6,6a-tetrahydro-3aH-cyclopenta[d]isoxazole 
• 34660-89-4 N-benzoyl-N-methylphenylglycine morpholide 
• 34660-90-7 N-methyl-N-[2-(2-morpholin-4-yl-cyclopent-1-enyl)-2-oxo-1-phenyl-ethyl]-benzamide 
• 39189-74-7 2-heptylidenecyclopentan-1-one 
• 36048-56-3 (2-morpholin-4-yl-cyclopent-1-enyl)-phenyl-cyclobutenedione 
• 16424-35-4 2-pentylidenecyclopentan-1-one 
• 40564-16-7 2-Octyliden-cyclopentanon 
• 2562-42-7 1-nitromethylcyclopentene 

Relevant academic research and scientific papers

Altering the allowed/forbidden gap in cyclobutene electrocyclic reactions: Experimental and theoretical evaluations of the effect of planarity constraints

The allowed conrotatory cyclobutene ring-opening has a distinctly nonplanar carbon skeleton. Classic experiments by Brauman and Archie, and by Freedman et al., placed the allowed/forbidden gap at greater than 15 kcal/mol. Wolfgang Roth proposed that a system forced to planarity might have a smaller preference for the conrotatory mode than unconstrained systems. Such systems have now been studied theoretically and experimentally, and results that confirm Roth's postulate are presented here. The experiments were performed in Bochum, and the calculations were carried out in Osaka and Los Angeles. As the cyclobutene ring-opening transition structure approaches planarity, the energy gap between allowed conrotatory and the forbidden disrotatory pathways decreases. For the ring-opening of a cyclobutene fused to norbornene, the energy gap between the forbidden and the allowed transition state is only 4.1 kcal/mol by CASSCF and 8.0 kcal/mol by CAS-MP2 as compared to 13.4 and 19.2 kcal/mol, respectively, for the parent cyclobutene. Experimental studies of 3,4-dimethylcyclobutenes fused to various ring systems are reported, and a trend is found toward a reduced allowed/forbidden gap as the planarity of the cyclobutene is enforced.

Diastereoselective Synthesis of Pyrazolines by Metal-Free Rearrangement of Bicyclic Triazolines

The metal-free preparation of diazoalkanes through the ring rearrangement of bicyclic triazolines is reported here. Their use in 1,3-dipolar cycloaddition reactions with electron-withdrawing alkenes was investigated. This synthetic procedure allows differently substituted pyrazolines to be obtained in few steps and with high atom economy.

Decomposition of an oxodiazirine: Free versus incarcerated within the cavities of two α-cyclodextrins

The chemistry of oxodiazirine 1 was investigated by photolyzing its α-cyclodextrin (6-Cy) complex, for which a Job plot indicated a 1:2 guest-to-host stoichiometry. Solid-phase photolysis of 16-Cy)2 produced tricyclo[3.3.0.02,8]octan-3-one (3) and bicyclo[3.3.0]oct-5- en-3-one (4) in a 93:7 ratio. In contrast, gas-phase thermolysis of free 1 resulted in a 47:53 ratio of products 3 and 4. Thus, incarceration of a guest compound within a fitting microenvironment of two host molecules leads to a strongly enhanced chemoselectivity, even when highly reactive species, such as carbenes, are involved.

Reaction of enamines with semicarbazone-based amidoalkylating reagents: A straightforward synthesis of annulated 1-aminopyrimidin-2-one derivatives

An efficient synthesis of 1-arylideneamino-substituted hexahydro-1H-cyclopenta[d]pyrimidin-2-ones and octahydroquinazolin-2-ones has been developed. The synthesis involves a stereo- and regioselective cascade reaction of the corresponding 4-(tosylmethyl)semicarbazones with 1-morpholinocyclopentene or 1-morpholinocyclohexene to give predominantly bicyclic pyrimidines with an exocyclic C[dbnd]C double bond (80–97%). The later undergo rapid isomerization when heated in THF in the presence of TsOH to form bicyclic pyrimidines with a significant predominance of those with an endocyclic C[dbnd]C double bond (90–97%).

Method for preparing alkane carboxylic acid by increasing alkane carbon chains

The invention discloses a method for preparing alkane carboxylic acid by increasing alkane carbon chains. The method comprises the following steps: (1) carrying out Stork enamine alkylation on cyclopentanone or cyclohexanone and a secondary amine compound to generate a corresponding 1-position secondary amine substituted cyclopentene or cyclohexene crude product, namely Stork enamine; (2) carrying out electrophilic reagent reaction on the Stork enamine and acyl halide to form a 2-acyl cyclic ketone compound; and (3) carrying out ring opening on the 2-acyl cyclic ketone compound under the action of alkali to generate a carbonyl carboxylic acid compound, and carrying out a Wolff-Huang Minglong reduction reaction on the carbonyl carboxylic acid compound to obtain the corresponding alkane carboxylic acid. According to the method disclosed by the invention, cyclopentanone or cyclohexanone can be flexibly selected to meet the requirement of increasing different carbon numbers according to the required carbon number and different sources of target carburant alkane carboxylic acid or corresponding acyl halide. The method has the advantages of simple reaction process and no complex operation difficulty, and is suitable for industrial mass production.

Discovery of quinolone derivatives as antimycobacterial agents

Tuberculosis (TB), an infectious disease caused byMycobacterium tuberculosis(M. tuberculosis), is an important public health issue. Current first-line drugs administered to TB patients have been in use for over 40 years, whereas second-line drugs display strong side effects and poor compliance. Additionally, designing effective regimens to treat patients infected with multi- and extremely-drug-resistant (MDR and XDR) strains of TB is challenging. In this report, we screened our compound library and identified compound1with antituberculosis activity and a minimal inhibitory concentration (MIC) againstM. tuberculosisof 20 μg mL?1. Structure optimization and the structure-activity relationship of1as the lead compound enabled the design and synthesis of a series of quinolone derivatives,6a1-6a2,6b1-6b36,6c1,6d1-6d14,7a1-7a2,7b1-7b2,7c1,8a1-8a5,9a1-9a4and10a1-10a6. These compounds were evaluatedin vitrofor anti-tubercular activity against theM. tuberculosisH37Rv strain. Among them, compounds6b6,6b12and6b21exhibited MIC values in the range of 1.2-3 μg mL?1and showed excellent activity against the tested MDR-TB strain (MIC: 3, 2.9 and 0.9 μg mL?1, respectively). All three compounds were non-toxic toward A549 and Vero cells (>100 and >50 μg mL?1, respectively). In addition, an antibacterial spectrum test carried out using compound6b21showed that this compound specifically inhibitsM. tuberculosis. These can serve as a new starting point for the development of anti-TB agents with therapeutic potential.

One-Pot Synthesis of 3-Oxocycloalka[c]pyridines

Abstract: A new efficient one-pot procedure has been developed for the synthesis of 1-substituted partially hydrogenated 3-oxocycloalka[c]pyridine-4-carbonitriles by reaction of cyclopentanone or cyclohexanone with morpholine, acyl chloride, and cyanoacetamide. The proposed procedure is advantageous due to shorter reaction time and smaller amounts of the solvents and reactants.

1 microwave-induced montmorillonite-mediated facile synthesis of enamines

Montmorillonite clay-mediated simple and high yielding protocol for the synthesis of various enamines with secondary amines and ketones is developed under microwave condition. This protocol is very convenient to accesses the enamines from cyclic amines with various carbonyl compounds in high yield under mild reaction conditions with short reaction time.

First zinc bromide promoted annulative domino reactions between enamines and cyclic Morita-Baylis-Hillman alcohols: Synthesis of N, O-ketals

A new efficient ZnBr 2-mediated annulative domino reaction between enamines and cyclic Morita-Baylis-Hillman (MBH) alcohols is disclosed. The process involves a tandem sequence (intermolecular conjugate addition of enamines to MBH alcohols and intramolecular nucleophilic addition of the hydroxyl moiety to the transiently generated iminium ion), affording the corresponding N, O -ketals diastereoselectively in good yields.

COMPOUNDS USEFUL IN THE TREATMENT OF AUTOIMMUNE AND INFLAMMATORY DISORDERS

The present invention relates to certain compounds of Formula (Ia) and pharmaceutically acceptable salts thereof, which exhibit useful pharmacological properties, for example, as agonists of the S1P1 receptor: Also provided by the present invention are pharmaceutical compositions containing compounds of the invention, and methods of using the compounds and compositions of the invention in the treatment of S1P1 receptor-associated disorders, for example, a disease or disorder mediated by lymphocytes, an autoimmune disease or disorder, an inflammatory disease or disorder, an inflammatory skin disease or disorder, cancer, psoriasis, atopic dermatitis, rheumatoid arthritis, Crohn's disease, transplant rejection, multiple sclerosis, systemic lupus erythematosus, ulcerative colitis, type I diabetes, and acne, microbial infections or diseases and viral infections or diseases.