629-60-7

Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

Safety Profile

Poison by intraperitoneal route.When heated to decomposition it emits toxic fumes ofNOx and CNí.

InChI:InChI=1/C13H25N/c1-2-3-4-5-6-7-8-9-10-11-12-13-14/h2-12H2,1H3

Upstream product

• 4292-19-7 1-Iodododecane 
• 151-50-8 potassium cyanide 
• 143-15-7 1-dodecylbromide 
• 10486-19-8 tridecanal 
• 109797-66-2 decyl isocyanide 
• 107-13-1 acrylonitrile 
• 51323-71-8 dodecyl mesylate 
• 7677-24-9 trimethylsilyl cyanide 
• 112-52-7 1-chlorododecane 
• 20965-27-9 7-bromo-heptanonitrile 
• 5414-21-1 5-bromopentan-1-nitrile 
• 14403-26-0 dioctylzinc 
• 42371-64-2 9-hexyl-9-borabicyclo[3.3.1]nonane 
• 592-41-6 1-hexene 

Downstream Products

• 2345-27-9 tetradecan-2-one 
• 28267-29-0 ethyl tridecanoate 
• 2869-34-3 1-tridecanamine 
• 5910-75-8 N,N-dimethyldodecyl amine 
• 5910-77-0 tri(tridecyl)amine 
• 112-40-3 dodecane 
• 149476-08-4 (1)-5-dodecyl-α-phenyl-2H-tetrazole-2-acetic acid 
• 149475-99-0 ethyl (1)-5-dodecyl-α-phenyl-2H-tetrazole-2-acetate 

Relevant academic research and scientific papers

Method for continuous preparation of nitriles in a pipelined reactor (by machine translation)

The method comprises the following steps that a tin catalyst is coated on the inner wall of the pipeline reactor; and the method comprises the following steps: coating a tin catalyst on the inner wall of the pipeline reactor. The amide solution and the catalytic auxiliary agent are mixed and then sent to a pipeline reactor, and the amide is dehydrated to generate nitrile at the reaction pressure of 0.1 - 2.0 mpa and 100 - 200 °C reaction temperature. The resulting reaction product was separated to give the crude product of the nitrile to which the amide corresponded. In the pipeline reactor, the corresponding nitrile is continuously prepared under the action of the tin catalyst, a dehydrating agent is not needed, byproducts only are water, and three wastes are reduced. (by machine translation)

One-pot synthesis of aldoximes from alkenes: Via Rh-catalysed hydroformylation in an aqueous solvent system

Aldoxime synthesis directly starting from alkenes was successfully achieved through the combination of hydroformylation and subsequent condensation of the aldehyde intermediate with aqueous hydroxylamine in a one-pot process. The metal complex Rh(acac)(CO)2 and the water-soluble ligand sulfoxantphos were used as the catalyst system, providing high regioselectivities in the initial hydroformylation. A mixture of water and 1-butanol was used as an environmentally benign solvent system, ensuring sufficient contact of the aqueous catalyst phase and the organic substrate phase. The reaction conditions were systematically optimised by Design of Experiments (DoE) using 1-octene as a model substrate. A yield of 85% of the desired linear, terminal aldoxime ((E/Z)-nonanal oxime) at 95% regioselectivity was achieved. Other terminal alkenes were also converted successfully under the optimised conditions to the corresponding linear aldoximes, including renewable substrates. Differences of the reaction rate have been investigated by recording the gas consumption, whereby turnover frequencies (TOFs) >2000 h-1 were observed for 4-vinylcyclohexene and styrene, respectively. The high potential of aldoximes as platform intermediates was shown by their subsequent transformation into the corresponding linear nitriles using aldoxime dehydratases as biocatalysts. The overall reaction sequence thus allows for a straightforward synthesis of linear nitriles from alkenes with water being the only by-product, which formally represents an anti-Markovnikov hydrocyanation of readily available 1-alkenes.

Radical cyanomethylation via vinyl azide cascade-fragmentation

Herein, a novel methodology for radical cyanomethylation is described. The process is initiated by radical addition to the vinyl azide reagent 3-azido-2-methylbut-3-en-2-ol which triggers a cascade-fragmentation mechanism driven by the loss of dinitrogen and the stabilised 2-hydroxypropyl radical, ultimately effecting cyanomethylation. Cyanomethyl groups can be efficiently introduced into a range of substrates via trapping of α-carbonyl, heterobenzylic, alkyl, sulfonyl and aryl radicals, generated from a variety of functional groups under both photoredox catalysis and non-catalytic conditions. The value of this approach is exemplified by the late-stage cyanomethylation of pharmaceuticals.

Double Dehydrogenation of Primary Amines to Nitriles by a Ruthenium Complex Featuring Pyrazole Functionality

A ruthenium(II) complex bearing a naphthyridine-functionalized pyrazole ligand catalyzes oxidant-free and acceptorless selective double dehydrogenation of primary amines to nitriles at moderate temperature. The role of the proton-responsive entity on the ligand scaffold is demonstrated by control experiments, including the use of a N-methylated pyrazole analogue. DFT calculations reveal intricate hydride and proton transfers to achieve the overall elimination of 2 equiv of H2.

Amino acid derived ionic liquid supported iron Schiff base catalyzed greener approach for the aerobic oxidation of amines to nitriles

Amino acid dl-threonine derived ionic liquid was treated with salicylaldehyde to give corresponding Schiff base which subsequently is complexed with iron and used as a green catalyst for aerobic oxidation of amines under solvent-less conditions. The developed catalyst was readily synthesized, reusable, and exhibited superior catalytic activity owing to the synergistic effect of ionic liquid moiety. The developed catalyst was found to be quite stable and could be reused for several runs without any significant loss in catalytic activity.

Structure-activity relationship studies of the lipophilic tail region of sphingosine kinase 2 inhibitors

Sphingosine-1-phosphate (S1P) is a ubiquitous, endogenous small molecule that is synthesized by two isoforms of sphingosine kinase (SphK1 and 2). Intervention of the S1P signaling pathway has attracted significant attention because alteration of S1P levels is linked to several disease states including cancer, fibrosis, and sickle cell disease. While intense investigations have focused on developing SphK1 inhibitors, only a limited number of SphK2-selective agents have been reported. Herein, we report our investigations on the structure-activity relationship studies of the lipophilic tail region of SLR080811, a SphK2-selective inhibitor. Our studies demonstrate that the internal phenyl ring is a key structural feature that is essential in the SLR080811 scaffold. Further, we show the dependence of SphK2 activity and selectivity on alkyl tail length, suggesting a larger lipid binding pocket in SphK2 compared to SphK1.

LONG CHAIN BASE SPHINGOSINE KINASE INHIBITORS

The invention relates to inhibitors of sphingosine kinase enzymatic activity, compounds and pharmaceutical compositions that inhibit sphingosine kinase 1 and sphingosine kinase 2 (SphK1 and SphK2) enzymes and further relates to methods of treating diseases and disorders mediated by sphingosine 1 phosphate activity, comprising administering an effective amount of sphingosine kinase inhibitors.

Radical cyanation of alkyl iodides with diethylphosphoryl cyanide

The β-elimination of an organophosphoryl group from an iminyl radical is observed for the first time. On the basis of this finding, radical cyanation of alkyl iodides is achieved by using diethylphosphoryl cyanide. Georg Thieme Verlag Stuttgart.

Polycyclic aromatic compounds-mediated electrochemical reduction of alkyl mesylates

Electrochemical reduction of alkyl mesylates was successfully carried out by using an undivided cell equipped with a Pt cathode and an Mg anode in the presence of biphenyl and t-BuOH. The reaction could proceed efficiently under mild conditions to give the corresponding alkanes in moderate to good yields. This procedure could also be applicable to chemoselective reduction of mesylates having functional groups such as epoxide, olefin, acetal, hydroxy, or cyano groups. Copyright