51382-01-5

Usage

Type of compound

Unsaturated amine

Double bond location

Between the first and second carbon atoms in the carbon chain

Usage

Building block in the synthesis of various chemicals and polymers

Applications

Production of surfactants, detergents, and corrosion inhibitors

Intermediate role

Production of specialty chemicals, pharmaceuticals, and agrochemicals

Production method

Amination reactions using 1-decene as the starting material

Importance

Versatile and valuable intermediate in the production of a wide range of products

Industrial significance

Used in various industries for its role in producing a diverse array of products

Upstream product

• 62871-09-4 10-bromodec-1-ene 
• 898543-34-5 10-azido-1-decene 
• 143557-87-3 Undec-10-enoyl azide 
• 38460-95-6 undec-10-enoyl chloride 
• 13019-22-2 9-Decen-1-ol 
• 85657-91-6 N-(dec-9-enyl)-2,2,2-trifluoroacetamide 

Downstream Products

• 313469-03-3 tert-butyl dec-9-enylcarbamate 
• 1266376-36-6 3,5-bis(1,1-dimethylethyl)-N-9-decen-1-yl-benzamide 

Relevant academic research and scientific papers

Update on the defensive chemicals of the little black ant, Monomorium minimum (Hymenoptera: Formicidae)

Alkaloids, including 2,5-dialkylpyrrolidines and 2,5-dialkylpyrrolines, have been reported to be components in the venom of little black ants, Monomorium minimum (Buckley). Two fatty amines were recently reported as minor compounds. By analyzing the discharge collected from the stinger apparatus (milking), this study revealed the presence of an additional seven compounds in the defensive secretion of this ant species. Compounds identified were 9-decenyl-1-amine, N-methylenedecan-1-amine, N-methylenedodecan-1-amine, 2-(1-non-8-enyl)-5-(1-hex-5-enyl)-1-pyrroline, N-methyl-2-(hex-5-enyl)-5-nonanyl-1-pyrrolidine, β-springene ((E,E)-7,11,15-trimethyl-3-methylene-1,6,10,14-hexadecatetraene) and neocembrene ((E,E,E)-1-isopropenyl-4,8,12-trimethylcyclotetradeca-3,7,11-triene). β-springene and neocembrene were found only in the defensive secretion of queens. Analyses of the contents of isolated poison and Dufour's glands of the queen indicated that all amines and alkaloids were from the poison gland and that β-springene and neocembrene were from the Dufour's gland. This demonstrated that the defensive secretion in M. minimum queens consists of components from both glands. This is also the first report on the natural occurrence of 9-decenyl-1-amine, N-methylenedecan-1-amine, and N-methyllenedodecan-1-amine.

Chemoenzymatic macrocycle synthesis using resorcylic acid lactone thioesterase domains

A key missing tool in the chemist's toolbox is an effective biocatalyst for macrocyclization. Macrocycles limit the conformational flexibility of small molecules, often improving their ability to bind selectively and with high affinity to a target, making them a privileged structure in drug discovery. Macrocyclic natural product biosynthesis offers an obvious starting point for biocatalyst discovery via the native macrocycle forming biosynthetic mechanism. Herein we demonstrate that the thioesterase domains (TEs) responsible for macrocyclization of resorcylic acid lactones are promising catalysts for the chemoenzymatic synthesis of 12- to 18-member ring macrolactones and macrolactams. The TE domains responsible for zearalenone and radicicol biosynthesis successfully generate resorcylate-like 12- to 18-member macrolactones and a 14-member macrolactam. In addition these enzymes can also macrolactonize a non-resorcylate containing depsipeptide, suggesting they are versatile biocatalysts. Simple saturated omega-hydroxy acyl chains are not macrocyclized, nor are the alpha-beta unsaturated derivatives, clearly outlining the scope of the substrate tolerance. These data dramatically expand our understanding of substrate tolerance of these enzymes and are consistent with our understanding of the role of TEs in iterative polyketide biosynthesis. In addition this work shows these TEs to be the most substrate tolerant polyketide macrocyclizing enzymes known, accessing resorcylate lactone and lactams as well as cyclicdepsipeptides, which are highly biologically relevant frameworks.

N-Methylation of Amines with Methanol at Room Temperature

N-Methylation of amines with methanol proceeds at room temperature in the presence of a silver-loaded titanium dioxide (Ag/TiO2) photocatalyst under UV-vis light irradiation. This method allows facile synthesis/isolation of N-methylamines bearing various functional groups including N-benzyl, N-allyl, N-Boc, hydroxyl, ether, acetal, carboxamide, formamide, and olefin groups. (Chemical Presented)

Design and synthesis of a macrosphelide A-biotin chimera

The rational design and synthesis of a biochemical probe of natural (+)-macrosphelide A, a potent cell-cell adhesion inhibitor, was completed to aid in the identification of its biological target. The key features of the synthesis include: (1) an efficient synthesis of the macrosphelide core structure using Yamaguchi-Hirao alkynylation, (2) a cross metathesis to connect a linker unit to the allyl-macrosphelide and (3) coupling of the linker-bound macrosphelide A with a chemical biotin tag. This journal is the Partner Organisations 2014.

Design, synthesis, and characterization of mesogenic amine-capped nematic gold nanoparticles with surface-enhanced plasmonic resonances

The use of the liquid-crystalline state to control the assembly of large (>5 nm) gold nanoparticles (NPs) is of considerable interest because of the promise of novel metamaterial properties of such systems. Here we report on a new approach for the prepara

Synthesis and biological evaluation of dihydromotuporamine derivatives in cells containing active polyamine transporters

Dihydromotuporamine C (4) and its 4,4-triamine analogue (5) were synthesized in good yield using ring-closing metathesis (RCM) methods. Comparison of their biological activities (Ki determinations in L1210 cells and IC50 determinations in L1210, CHO, and CHO-MG cells) revealed that the motuporamine derivatives do not use the polyamine transporter (PAT) for cellular entry. Bioevaluation of a N1-(anthracen-9- ylmethyl)-n1-(ethyl)homospermidine control (7) revealed that the presence of a N1 tertiary amine center imparted a significant reduction in the PAT affinity of the polyamine conjugate and abolished its PAT-targeting selectivity.

Halogen-modified silicon, surfaces

Chemically-modified surfaces on unoxidized, bromine- or iodine-terminated carbon, silicon, and germanium substrates are disclosed. Visible light mediates the reaction of protected ω-modified, α-unsaturated aminoalkenes (preferred) with bromine- or iodine-terminated carbon, silicon, or germanium surfaces. Removal of the protecting group yields an aminoalkane-modified silicon surface. These amino groups can be coupled to terminal-modified oligonucleotides using a bifunctional crosslinker, thereby permitting the preparation of modified surfaces and arrays. Methods for controlling the surface density of molecules attached to the substrate are also disclosed.

Modified carbon, silicon, and germanium surfaces

Chemically-modified surfaces on unoxidized carbon, silicon, and germanium substrates are disclosed. Ultraviolet radiation mediates the reaction of protected ω-modified, α-unsaturated aminoalkenes (preferred) with hydrogen-terminated carbon, silicon, or germanium surfaces. Removal of the protecting group yields an aminoalkane-modified silicon surface. These amino groups can be coupled to terminal-modified oligonucleotides using a bifunctional crosslinker, thereby permitting the preparation of modified surfaces and arrays. Methods for controlling the surface density of molecules attached to the substrate are also disclosed.

Pd/C(en)-catalyzed chemoselective hydrogenation with retention of the N-Cbz protective group and its scope and limitations

A chemoselective method for the hydrogenation of acetylene, olefin, azide, nitro and benzyl ester functionalities with retention of the aliphatic N-Cbz group was established. The chemoselectivity was accomplished by using a combination of 5% Pd/C-ethylenediamine [5% Pd/C(en)] and THF (or 1,4-dioxane) as a solvent, and the scope and limitations of this methodology were investigated. These results reinforce the utility of N-Cbz protective groups in synthetic chemistry, especially in peptide synthesis. (C) 2000 Elsevier Science Ltd.