Butan-2-amine

Amines whose chirality stems from the presence of asymmetric carbon atoms. Most chiral amines fall into this group. Nitrogen inversion is irrelevant because nitrogen is not the chirality center. For example, butan-2-amine can be resolved into enantiomers because the 2-butyl group is chiral. 

For example, when butan-2-amine is exhaustively methylated, converted to the hydroxide salt, and heated, elimination takes place to form a mixture of but-l-ene and but-2-ene. 

Hofmann elimination of exhaustively methylated butan-2-amine. The most stable conformation of the C2—C3 bond has no proton on C3 in an anti relationship to the leaving group. Along the Cl —C2 bond, however, any staggered conformation has an anti relationship between a proton and the leaving group. Abstraction of a proton from Cl gives the Hofmann product. 

A is butan-2-amine B is diethylamine. 19.53. 2,2-dimethyl-propan-1-amine. 

Fig. 4. Peptide and chemical structure, respectively, of the incretin mimetics exenatide and liraglutide and the DPP inhibitors sitagliptin ((2R)A-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[l,2,4]triazolo[4,3-a]pyrazin-7(8//)-yl]-l-(2,4,5-trifluorophenyl)butan-2-amine) and vUdagliptin (l-[[(3-hydroxy-l-adamantyl)amino]acetyl]-2-cyano-(S)-pyrrolidine). (Modified from Drucker and Nanck 2006 [145]).

The DDP-4 inhibitors are chemically variable and their metabolic pathways are different. Sitagliptin, (2f )-4-oxo-4[3-(tri-fluoromethyl)-5,6-dihydrol[l,2,4]triazolol[4, 3-a]pyrazin-7(8H)-yl]-l-(2,4,5-trifluorophe-nyl)butan-2-amine, is primarily eliminated unchanged, 80% being excreted in the... 

The most known designer drugs are carphedone 4-chloro-2,5-dimethoxyphenethylamine (2C-C) i 5-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yM-methylpiperazine-l-carboxylate (zopiclone or Z-drug) 4-(N,N-dimethylamino sulfonyl)-7-fluoro-2,l,3-benzoxadiazole (DBD-F) dimethyltryptamine (DMTA) diphenydramine 4-ethyl-2,5-dimethoxyphenethylamine (2C-E) 4-ethylthio-2,5-dimethoxyphenethylamine (2C-T-2) 4-fluoroamphetamine (4-FMP) indan-2-amine 4-iodo-2,5-dimethoxyphenethylamine (2C-I) 1 -(4-iodo-2,5-dimethoxyphenyl)propan-2-amine (DOI) 4-isopropylthio-2,5-dimethyoxyphenethylamine (2C-T-4) meperidine 2-methylamino-l-(3,4-methylenedioxyphenyl)butan-l-one (Bk-MBDB) l-(3,4-methylenedioxybenzyl)piperazine (MDBP) 1 -(3,4-methylenedioxyphenyl)butan-2-amine (BDB) N-methyl-3,4-methylenedioxymethamphetamine (MMDA-2) N-methyl-1 -(3,4-methylenedioxyphenyl)butan-2-amine (HMDMA) N-methyl-l-(3,4-methylenedioxyphenyl)butan-3-amine (HMDMA) methylphenidate 4-methoxymethamphetamine (PMMA) l-(4-methoxyphenyl)piperazine (4-MPP) 2-(6-methyl-2-p-tolylimidazol[l,2-9]pyridine-3-yl)acetamide (zolpidem) normeperidine 4-phenylbutylamine (4-PBA) 3-phenyl-1-peopyTamine (3-PPA) and 2,4,6-trimethoxyamphetamine (TMA-6). 

Kim D, Wang L, Beconi M, Eirmann GJ, Fisher MH, He H, Hickey GJ, Kowalchick JE, Leiting B, Lyons K, Marsilio E, McCann ME, Patel RA, Petrov A, Scapin G, Patel SB, Roy RS, Wu JK, Wyvratt MJ, Zhang BB, Zhu L, Thornherry NA, Weber AE. (2R)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro [l,2,4]triazolo[4,3-a]pyrazin-7(8/0-yl]-l-(2,4,5-trifluoro-phenyl)butan-2-amine a potent, orally active dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes. J. Med. Chem. 2005 48 141-151. 

How would you synthesize (R)-butan-2-amine from (S)-butan-2-ol ... 

Beilstein Handbook Reference) A13-15424 Amine, tributyl- BRN 1698872 CCRIS 4879 EINECS 203-058-7 HSDB 877 N,N-Dibutyl-1-butan-amine Tri-n-butylamine Tributilamina Tributylamine Tris-n-butylamine UN2542 UN3254. Clear liquid mp = -70° bp = 216.5° d O = 0.7770 Xm = 242 nm (e = 1000, CHCI3) slightly soluble in H2O, CCI4, soluble in Me2CO, CeHe, very soluble... 

Four methylenedioxyamphetamines [3,4-methylenedioxy-methamphetamine and -ethamphetamine, and A -methyl- and Af-ethyl-l-[l,3-benzodioxol-5-yl]-2-butan-amine) were baseline resolved using a C,g column (A = 280 ran) and a linear 25-min 95/5 - 20/80 water (0.1 M triethylammonium acetate at pH 7.3)/ acetonitrile gradient. Standard concentrations ranged from 300 pg/mL to 4 mg/mL [1424]. 

Meth an amine Methanamine, Br Ethan amine Ethanamine, Br 1-Propanamine 1-Butan amine 1-Butanamine, Br 1-Butanamine, NO3 1-Pentanamine 1-Hexanamine 1-Hexanamine, Br 1-Heptanamine N-Methyhnethanamine N-Methyknethanamine, Cl N-Ethylethan amine... 

Flares are mostly used for the disposal of hydrocarbons. Waste gases composed of natural gas, propane, ethylene, propylene, butadiene, and butane probably constitute over 95 percent of the material flared. Flares have been used successfully to control malodorous gases such as mercaptans and amines, but care must be taken when flaring these gases. Unless the flare is very efficient and gives good combustion, obnoxious fumes can escape unburned and cause a nuisance. 

The synthesis of 1-ethoxy-1-butjme has been reported previously, but the preparations have required multistep sequences. Two of the procedures use 1,2-dibromo-l-ethoxy butane which is dehydrohalogenated in two successive steps, first by an amine base and then by either powdered potassium hydroxide or sodium amide no yields are given. The... 

Purely parallel reactions are e.g. competitive reactions which are frequently carried out purposefully, with the aim of estimating relative reactivities of reactants these will be discussed elsewhere (Section IV.E). Several kinetic studies have been made of noncompetitive parallel reactions. The examples may be parallel formation of benzene and methylcyclo-pentane by simultaneous dehydrogenation and isomerization of cyclohexane on rhenium-paladium or on platinum catalysts on suitable supports (88, 89), parallel formation of mesityl oxide, acetone, and phorone from diacetone alcohol on an acidic ion exchanger (41), disproportionation of amines on alumina, accompanied by olefin-forming elimination (20), dehydrogenation of butane coupled with hydrogenation of ethylene or propylene on a chromia-alumina catalyst (24), or parallel formation of ethyl-, methylethyl-, and vinylethylbenzene from diethylbenzene on faujasite (89a). 

The second option involves the incorporation of either chiral amines or chiral alcohols into the heteroatom-carbene side chain (R ), which represents the most versatile approach to diastereoselective benzannulation. The optically pure (2R,3R)-butane-2,3-diol was used to tether the biscarbene complex 37. The double intramolecular benzannulation reaction with diphenylbutadiyne allowed introduction of an additional stereogenic element in terms of an axis... 

However, this is obviously not always the case, a counter example being the transformation of P-tetralone (23) to (S)—anunotetralin (24), with 2-amino butane serving as the amine donor. The of an (S)-selective aminotransaminase leads to a value of only... 

Recent efforts in the development of efficient routes to highly substituted yS-ami-no acids based on asymmetric Mannich reactions with enantiopure sulfmyl imine are worthy of mention. Following the pioneering work of Davis on p-tolu-enesulfmyl imines [116], Ellman and coworkers have recently developed a new and efficient approach to enantiomerically pure N-tert-butanesulfmyl imines and have reported their use as versatile intermediates for the asymmetric synthesis of amines [91]. Addition of titanium enolates to tert-butane sulfmyl aldimines and ketimines 31 proceeds in high yields and diastereoselectivities, thus providing general access to yS -amino acids 32 (Scheme 2.5)... 

Precursors and Formation. Tobaccos used for commercial products in the U.S.A, contain between 0,5 and 2,7% alkaloids. Nicotine constitutes 85-95% of the total alkaloids (14,26,27). Important minor alkaloids are nornicotine, anatabine, anabasine, cotinine and N -formylnornicotine (Figure 6), Several of these alkaloids are secondary and tertiary amines and, as such, amenable to N-nitrosation. The N-nitrosated alkaloids identified to date in tobacco and tobacco smoke include N -nitrosonornico-tine (NNN), 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanone (NNK) and N -nitrosoanatabine (NAT Figure 7). In model experiments, nitrosation of nicotine also yielded 4-(methylnitrosamino)-4-(3-pyridyl)butanal (NNA 28). 

Along another line of work in our group (S,S)-l,4-bis(dimethylamino)-2,3-dimethoxy butane (DDB), which had been used as cosolvent in asymmetric synthesis [113], was tested as a core moiety for a dendritic amine catalyst. The conformationally flexible DDB-core, which has been synthesized in five steps from diethyl tartrate was coupled with different branches to give dendritically expanded diamines 90-92 (molecular weight 3800 Da) [114] (Fig. 32). 

The first example of this type of transformation was reported in 1974 [76]. Three catalysts were investigated, namely [Co2(CO)8], [Co(CO)g/PBu ], and [Rh6(CO)i6]. The [Co OJg/PBu ] catalyst showed activity for reductive animation using ammonia and aromatic amines. The [Rh6(CO)16] catalyst could be used for reductive animation using the more basic aliphatic amines that were found to poison the cobalt catalyst. This early report pointed out that the successful reductive animation of iso-butanal (Me2CCHO) with piperidine involves selective enamine hydrogenation, that reductive animation of cyclohexanone with isopropylamine probably involves imine hydrogenation, and that reductive amination of benzaldehyde with piperidine would presumably involve the reduction of a carbinolamine. 

Irradiation of styrenes in the presence of tertiary aliphatic amines resulted in the formation of adducts in fair to poor yield25. Excited styrene7 reacted with triethylamine to yield diastereomeric adducts 12, 1-phenylethane 16 and 2,3-diphenyl butane 1926 (equation 3). 

D. Mandler and 1. Willner, Photosensitized NAD(P)H regeneration systems application in the reduction of butan-2-one, pyruvic, and acetoacetic acids and in the reductive amination of pyruvic and oxoglutaric acids to amino acids,... 

Uses Solvent in nitrocellulose coatings, vinyl films and Glyptal resins paint removers cements and adhesives organic synthesis manufacture of smokeless powders and colorless synthetic resins preparation of 2-butanol, butane, and amines cleaning fluids printing catalyst carrier acrylic coatings. 

Synonyms AI3-24197 1-Aminobutane BRN 0605269 Butan-l-amine 1-Butanamine n-Butylamine CCRIS 4756 EINECS-203-699-2 FEMA No. 3130 Monobutylamine Mono-/3-but-ylamine Norralamine Norvalamine NSC 8029 Tutane UN 1125. 

Several other non-nitrogenous products have been identified as products of the Maillard reaction. These include butanol, butanone, butane-dione, and pentane-2,3-dione as well as dihydroxyacetone, glycer-aldehyde, and D-erythrose. Obviously, the same products are present after mild acidic or basic degradation of carbohydrates. Thus, the necessity of an amine or amino acid in the mechanism of their formation is uncertain. 

For amines having an a-hydrogen atom, electrochemical oxidation leads to the imine as the first detectable intemrediate. In the absence of another nucleophile, this is not usually a useful reaction since the imine is hydrolysed by water present in the solvent leading to a mixture of products [80, 81], Oxidation of ten-butylamine, which has no a-hydrogen atom, leads to loss of a proton flrom the nitrogen atom and the dimerization of nitrogen centred radicals. The product isolated in moderate yields is azo-teri-butane 17 [82], The reaction can be carried out in an... 

Auch bei der Weidenhagen-Synthese kann man analog der Radziszewski-Reaktion einen Teil des Ammoniaks durch ein primares Amin ersetzen und somit 1-substituierte Imidazole herstellen. Beim Einsatz unsymmetrisch substituierter a-Hydroxy-ketone erhalt man dann Iso-meren-Gemische. So entstehen aus l,4-Dihydroxy-2-oxo-butan mit verschiedenen Aldehyden, Ammoniak und primaren Aminen Gemische der entsprechenden 1-substituierten 4- bzw. 5-(2-Hydroxy-ethyl)-imidazole34 ... 

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