5048-44-2

Usage

InChI:InChI=1/C12H21N/c1-2-3-4-5-6-7-8-9-10-11-12-13/h2H,1,3-11H2

Upstream product

• 112-43-6 10-Undecen-1-ol 
• 7766-50-9 1-undecen-11-ylbromide 
• 151-50-8 potassium cyanide 
• 1675-20-3 Trifluoressigsaeure-undecen-10-ylester 
• 143-33-9 sodium cyanide 
• 51148-67-5 10-undecen-1-yl p-toluenesulfonate 
• 52355-50-7 undec-10-en-1-yl methanesulfonate 
• 95386-96-2 Acetic acid 11-cyano-undecyl ester 
• 35042-91-2 11-cyanoundecanoyl chloride 
• 5810-18-4 11-cyanoundecanoic acid 
• 73782-16-8 12-hydroxydodecanoic nitrile 
• 112-38-9 10-undecenoic acid 
• 13019-22-2 9-Decen-1-ol 
• 66605-77-4 9-decenyl p-toluenesulfonate 

Downstream Products

• 51148-68-6 dodec-11-enal 
• 54863-47-7 12-bromododecanenitrile 
• 2984-55-6 2-hydroxydodecanoic acid 
• 35289-31-7 dodec-11-en-1-ol 
• 177431-83-3 (2-Dodec-11-enyl-2H-tetrazol-5-yl)-phenyl-acetic acid 
• 1026563-20-1 (2-Dodec-11-enyl-2H-tetrazol-5-yl)-phenyl-acetic acid ethyl ester 
• 99824-64-3 dodec-11-en-1-yl 4-methylbenzenesulfonate 
• 16900-60-0 dodec-11-ynoic acid 
• 58879-40-6 tetradeca-1,13-dien-3-one 
• 1286254-45-2 C₂₅H₃₇N 

Relevant academic research and scientific papers

EXTRAHEPATIC DELIVERY

One aspect of the present invention relates to a compound comprising an antisense strand which is complementary to a target gene; a sense strand which is complementary to said antisense strand; and one or more lipophilic monomers, containing one or more lipophilic moieties, conjugated to one or more positions on at least one strand, optionally via a linker or carrier. Another aspect of the invention relates to a method of gene silencing, comprising administering to a cell or a subject in need thereof a therapeutically effective amount of the lipophilic monomer-conjugated compound.

A General Acid-Mediated Hydroaminomethylation of Unactivated Alkenes and Alkynes

In comparison to the extensively studied metal-catalyzed hydroamination reaction, hydroaminomethylation has received significantly less attention despite its considerable potential to streamline amine synthesis. State-of-the-art protocols for hydroaminomethylation of alkenes rely largely on transition-metal catalysis, enabling this transformation only under highly designed and controlled conditions. Here we report a broadly applicable, acid-mediated approach to the hydroaminomethylation of unactivated alkenes and alkynes. This methodology employs cheap, readily available, and bench-stable reactants and affords the desired amines with excellent functional group tolerance and impeccable regioselectivity. The broad scope of this transformation, as well as mechanistic investigations and in situ domino functionalization reactions are reported.

PRODUCTION OF AMINES VIA A HYDROAMINOALKYLATION REACTION

Provided is a process for producing an amine via a hydroaminoalkylation reaction of a non-aromatic C-C double bond or C-C triple bond, said process comprising a step of reacting a compound comprising a non-aromatic C-C double bond or C-C triple bond with a reactive component which is obtainable by combining an aminal or a hemiaminal ether with an acidic medium comprising trifluoroacetic acid, wherein the aminal contains two amino groups independently selected from a secondary and a tertiary amino group that are linked by a methylene group wherein one hydrogen atom may be replaced by a further substituent, and at least one of the amino groups carries a hydrogen atom at a carbon atom bound in α-position to its nitrogen atom, and the hemiaminal ether contains a secondary or a tertiary amino group which carries a hydrogen atom at a carbon atom bound in α-position to its nitrogen atom, and the secondary or tertiary amino group is linked to an alkoxy group by a methylene group wherein one hydrogen atom may be replaced by a further substituent.

Nitrile-promoted Rh-catalyzed intermolecular hydroacylation of olefins with salicylaldehyde

Rh-catalyzed intermolecular hydroacylation between salicylaldehyde and alkenylnitriles proceeded at room temperature to preferentially give normal-hydroacylated products. Addition of CH3CN and NaOAc accelerated the Rh-catalyzed hydroacylation of monoolefins to exclusively produce the normal-hydroacylated products under mild reaction conditions. Plausible mechanisms for the regioselections are also described.

The reduction of α,β-unsaturated nitriles and α-halonitriles with sodium hydrogen telluride

Sodium hydrogen telluride reacts chemoselectively with α,β- unsaturated nitriles and α-halonitriles linked to aromatic and aliphatic substituents to corresponding saturated nitriles with good yields.

Inhibitors of acyl-CoA:cholesterol O-acyltransferase. Synthesis and pharmacological activity of (±)-2-dodecyl-α-phenyl-N-(2,4,6- trimethoxyphenyl)-2H-tetrazole-5-acetamide and structurally related tetrazole amide derivatives

A series of tetrazole amide derivatives of (±)-2-dodecyl-α-phenyl-N- (2,4,6-trimethoxyphenyl)-2H-tetrazole-5-acetamide (1) was prepared and evaluated for their ability to inhibit acyl-CoA: cholesterol O- acyltransferase (ACAT) in vitro and to lower plasma total cholesterol in vivo. For this series of compounds, our objective was to systematically replace substituents appended to the amide and tetrazole moieties of 1 with structurally diverse functionalities and assess the effect that these changes have on biological activity. The ensuing structure-activity relationship (SAR) studies identified aryl (7b) and heteroaryl (7f,g) replacements for 2,4,6-trimethoxyphenyl that potently inhibit liver microsomal and macrophage ACAT in vitro and exhibit good cholesterol lowering activity (56-66% decreases in plasma total cholesterol at 30 mg/kg), relative to 1, when compared in the acute rat model of hypercholesterolemia. Replacement of the α-phenyl moiety with electron-withdrawing substituents (13e-h), however, significantly reduced liver microsomal ACAT inhibitory activity (IC50 > 1 μM). This is in contrast to electron-donating substituents (13ij,m-q), which produce IC50 values ranging from 5 to 75 nM in the hepatic microsomal assay. For selected tetrazole amides (1, 7b, 13n,o), reversing the order of substituents appended to the 2- and 5-positions in the tetrazole ring (36a- d), in general, improved macrophage ACAT inhibitory activity and provided excellent cholesterol-lowering activity (ranging from 65% to 77% decreases in plasma total cholesterol at 30 mg/kg) in the acute rat screen. The most potent isomeric pair in this set of unsubstituted methylene derivatives (13n and 36a) caused adrenocortical cell degeneration in guinea pigs treated with these inhibitors. In contrast, adrenal glands taken from guinea pigs treated with the corresponding α-phenyl-substituted analogs (7b and 36c) were essentially unchanged compared to untreated controls. Subsequent evaluation of 7b and 36c in a rabbit bioassay showed that both compounds and/or their metabolites were present in plasma after oral dosing. Unlike 7b and 36c, compound 1 and related 2,4,6-trimethoxyanilides (13j, 30c,d) showed poor oral activity in the rabbit bioassay. Nevertheless, in cholesterol-fed rabbits, both systemically available (7b, 36c) and poorly absorbed inhibitors (1, 36d) were more effective in lowering plasma total cholesterol than the fatty acid amide CI-976.

A general approach to enantiomerically pure methylcarbinols. Asymmetric synthesis of antibiotic (-)-A26771B and the WCR sex pheromone

Either (R) or (S) enantiomerically pure methylcarbinol groups are conveniently produced from monosubstituted alkenes via the Sharpless asymmetric dihydroxylation (AD) reaction. The initial AD product, 1,2- dihydroxyalkane, obtained with predictable absolute configuration and high enantiomeric purity, is converted into 2-acetoxy-1-bromoalkane and then subjected to reductive debromination. These conditions are compatible with a variety of functional groups, including acetal, ester, nitrile, ketone, and silyl ether. The advantages of this method are demonstrated by highly efficient, asymmetric syntheses of enantiomerically pure natural products. All four stereoisomers of the WCR sex pheromone 4 are prepared in six steps form nona-1,8-diene in 10-15% overall yield. Similarly, a highly efficient formal total synthesis of antibiotic (-)-A26771B (5) is accomplished via two alternative approaches. The first one transforms dodec-11-enal into enantiomerically pure 5 in 11 steps and 4.1% overall yield, while the second achieves the same transformation in 12 steps and 6.6% overall yield.

A SIMPLE ONE-POT SYNTHESIS OF NITRILES FROM ALCOHOLS

Primary alcohols are cleanly converted into nitriles in excellent yields by a new, one-pot, two-step process, involving transformation into the corresponding trifluoroacetates followed by nucleophilic substitution reaction with sodium cyanide.

SYNTHESIS OF CROWN ETHERS BONDED TO A POLYSTYRENE MATRIX THROUGH AN AMIDO LINKAGE AND THEIR USE AS PHASE-TRANSFER CATALYSTS

Condensation of amino-functionalized crown ethers with microporous polystyrene bearing carboxyl groups afforded catalysts 15-18, in which the macrocyclic polyether is linked to the matrix through an amino bond.These catalysts are efficient anion activators in aliphatic nucleophilic substitutions under phase-transfer conditions.