10416-67-8

Usage

Uses

Used in Organic Synthesis:
N-Trimethylsilylphthalimide is used as a reagent for the transformation of alcohols into silyl ethers, which is crucial for protecting the hydroxyl groups during various chemical reactions. This transformation allows for the selective modification of functional groups in complex organic molecules.
Used in Peptide and Amino Acid Protection:
In the synthesis of peptides and amino acids, N-Trimethylsilylphthalimide is utilized for the protection of amino groups. This protection is essential to prevent unwanted side reactions and to ensure the successful formation of the desired peptide or amino acid sequence.
Used in Pharmaceutical and Fine Chemical Synthesis:
N-Trimethylsilylphthalimide also serves as a precursor in the synthesis of various pharmaceuticals and fine chemicals. Its unique properties enable the development of new compounds with potential therapeutic applications, contributing to the advancement of the pharmaceutical industry.
Used in Research and Development:
Due to its stability and compatibility with a wide range of reaction conditions, N-Trimethylsilylphthalimide is a valuable tool in research and development laboratories. It aids chemists in exploring new synthetic pathways and developing innovative methods for the preparation of complex organic compounds.

InChI:InChI=1/C11H13NO2Si/c1-15(2,3)12-10(13)8-6-4-5-7-9(8)11(12)14/h4-7H,1-3H3

Upstream product

• 136918-14-4 phthalimide 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 75-77-4 chloro-trimethyl-silane 
• 1074-82-4 potassium phtalimide 
• 85-44-9 phthalic anhydride 
• 100-42-5 styrene 
• 7677-24-9 trimethylsilyl cyanide 
• 422508-64-3 1,3-dioxoisoindolin-2-yl 2,3,4,5,6-pentafluorobenzoate 
• 1538551-54-0 1,3-dioxoisoindolin-2-yl butyrate 
• 24182-36-3 [(1Z)-2-bromobuta-1,3-dien-1-yl]benzene 

Downstream Products

• 1041262-62-7 ethyl (1S,5S)-5-(1,3-dioxoisoindolin-2-yl)cyclohex-3-enecarboxylate 
• 79293-84-8 N-(tert-butyldimethylsilyl)phthalimide 
• 1291089-95-6 (1R,3S,4R)-ethyl 3-(1,3-dioxoisoindolin-2-yl)-4-(4-methylphenylsulfonamido)-5-oxocyclohexanecarboxylate 
• 1291089-93-4 (1R,3S,4R,5R)-ethyl 3-(1,3-dioxoisoindolin-2-yl)-5-hydroxy-4-(4-methylphenylsulfonamido)cyclohexanecarboxylate 
• 1291090-01-1 C₂₃H₂₁NO₄Se 
• 1291089-91-2 (1S,3R,5S,6R)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-7-tosyl-7-aza-bicyclo[4.1.0]heptane-3-carboxylate 
• 1291089-92-3 C₂₄H₂₄N₂O₆S 
• 1291089-94-5 C₂₄H₂₆N₂O₇S 
• 1291089-98-9 (3R,4R,5S)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-4-(4-methylphenylsulfonamido)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 
• 1041262-64-9 ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)cyclohexa-1,3-dienecarboxylate 
• 1041262-63-8 ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)-1-(phenylthio)cyclohex-3-enecarboxylate 
• 1041262-68-3 (3R,4R,5S)-4-acetamido-5-(1,3-dioxoisoindol-2-yl)-3-(pentyl-3-yloxy)cyclohexyl-ethyl-1-ene-1-carboxylate 
• 1041262-67-2 ethyl (3R,4R,5S)-5-(1,3-dioxoisoindolin-2-yl)-3-(pentan-3-yloxy)-4-{N-[2-(trimethylsilyl)ethylsulfonyl]acetamido}cyclohex-1-enecarboxylate 
• 1041262-70-7 (1R,4S,5S)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-1-(pentan-3-yloxy)-4-(2-(trimethylsilyl)ethylsulfonamido)cyclohex-2-enecarboxylate 

Relevant academic research and scientific papers

Strong influence of intramolecular Si?O proximity on reactivity: Systematic molecular structure, solvolysis, and mechanistic study of cyclic N-trimethylsilyl carboxamide derivatives

A comparative alcoholysis study of N-silylated derivatives of simple heterocyclic carboxamides (lactams, imides, ureas) is presented. The second-order rate constant values span a range as wide as three orders of magnitude. On the basis of DFT calculations, a good correlation between reactivity and the Si?O distance was found within each family of compounds. The viability of two different reaction pathways was evaluated using a detailed computational mechanistic study of the methanolysis of cyclic urea homologues. Peculiarities in the single-crystal X-ray diffraction structures of the trimethylsilyl and trimethylsiloxy phthalimides are also discussed.

Reaction of hexamethyldisilazane with cyclic anhydrides of organic acids: A new route to N-trimethylsilylimides of di- and tetracarboxylic acids

Cyclic anhydrides of di- and tetracarboxylic acids react with hexamethyldisilazane to give the corresponding N-trimethylsilylimides in 90-96% yields. However, cyclic anhydrides of succinic, 4-nitrophthalic, and tetrachlorophthalic acids react differently, giving acyclic trimethylsilyl esters of mono-N-trimethylsilylamides of these acids in 90-93% yields. The 1H NMR, IR, and mass spectra of the compounds synthesized were studied.

Selective C=O reduction in phthalimide with nickel(0) compounds

The catalytic reduction of phthalimide was achieved using nickel catalysts. The use of catalytic amounts (20% mol) of [Ni(COD)2] or [(dippe)Ni(μ-H)]2 (1) allowed the monoreduction of phthalimide to yield isoindolinone and benzamide, at 140-180 C and 750 psi of H2. When the N-H moiety of phthalimide was protected with a trimethylsilyl group, both C=O groups were reduced to yield (trimethylsilyl)isoindoline. However, when a methyl moiety was used as the protecting group, the C=O groups and the aromatic ring were reduced, using rather similar reaction conditions, due to the formation of 5 A (average) nickel nanoparticles.

Metal-to-Ligand Ratio-Dependent Chemodivergent Asymmetric Synthesis

Chemodivergent asymmetric synthesis was achieved by tuning the metal-to-ligand ratio in an organometallic catalytic system. Using N-(aroyloxy)phthalimide as the precursor of either an oxygen-centered aroyloxy radical or a nitrogen-centered phthalimidyl radical, enantioselective oxocyanation or aminocyanation of alkenes was achieved separately through a dual photoredox and copper catalysis. The metal-to-ligand ratio can exert chemoselective control while retaining the high enantiopurity of divergent products. Both reactions proceed efficiently with catalyst loading as low as 0.2 mol % and can be performed on a gram scale without loss of chemoselectivity or enantioselectivity. Chemodivergent asymmetric 1,5-aminocyanation or 1,5-oxocyanation of vinylcyclopropane can also be realized by this protocol. Mechanistic investigations involving electron paramagnetic resonance (EPR) experiments were performed to shed light on the stereochemical and chemodivergent results.

Enantioselective Radical Carbocyanation of 1,3-Dienes via Photocatalytic Generation of Allylcopper Complexes

1,3-Dienes are readily available feedstocks that are widely used in the laboratory and industry. However, the potential of converting 1,3-dienes into value-Added products, especially chiral products, has not yet been fully exploited. By synergetic photoredox/copper catalysis, we achieve the first visible-light-induced, enantioselective carbocyanation of 1,3-dienes by using carboxylic acid derivatives and trimethylsilyl cyanide. Under mild and neutral conditions, a diverse range of chiral allyl cyanides are produced in generally good efficiency and with high enantioselectivity from bench-stable and user-safe chemicals. Moreover, preliminary results also confirm that this success can be expanded to 1,3-enynes and the four-component carbonylative carbocyanation of 1,3-dienes and 1,3-enynes.

Polysulfonylamines, XXXVI, Trimethylsilyl Dimesylamine: Preparation, NMR-Spectroscopic Characterization, and Reactivity as a Silylating Agent

(CH3)3SiN(SO2CH3)2 (1), m.p. 69-70 deg C, is obtained by metathesis of AgN(SO2CH3)2 with (CH3)3SiCl (improvement of a known procedure) or, more conveniently, by silylation of HN(SO2CH3)2 with 2NH.The (1)H, (13)C and (29)Si NMR solution spectra and the (29)Si NMR solid-state spectrum suggest the constitution of 1 in solution (CDCl3, CD2Cl2, CDCl2-CDCl2) to be an equilibrium mixture of the N-silylated form (CH3)3Si-N(SO2CH3)2 (I) and the O-silylated form (CH3)3Si-O-S(O)(CH3) = NSO2CH3 (II) in a molar ratio of 2:1 at room temperature, whereas in the known crystal structure of 1 only form I is present.The solid-state NMR experiment acted as a bridge between X-ray crystallography and solution-state NMR, enabling assignments of the resonances to be made with confidence to the tautomers.At room temperature, form II undergoes a rapid intramolecular 1.5-migration of silicon between oxygen centers of the two sulfonyl groups.As shown by kinetic measurements using (1)H NMR spectroscopy, 1 is a highly reactive agent for silylating ketones in the presence of triethylamine.Hydroxy and thiol functions, even when sterically hindered, are silylated by 1 in uncatalyzed reactions.It is further shown that HN(SO2CH3)2 is an efficient catalyst for silylations with 2NH. Key words: Polysulfonylamines, Trimethylsilyl Dimesylamine, N,O- and O,O-Silyl Migration, Silylation of Hydroxy and Thiol Functions, Solid State (29)Si NMR

SYNTHESIS OF EXTENDED ACYCLIC AZATHIENES WITH AROMATIC SUBSTITUENTS. III. PHTHALIMIDO GROUP AS THE LEAVING GROUP

The use of the phthalimido group as the leaving group makes it possible to obtain asymmetric 1,7-diaryl-1,3,5,7-tetraaza-2,4,6-trithia-1,2,5,6-heptatetraenes, which are not obtainable by the previously known methods.Cesium fluoride in acetonitrile increases the nucleophilicity of the nitrogen atom of the N-trimethylsilyl derivatives of acyclic azathienes and phthalimide.In acetonitrile solution a spontaneous shortening of the sulfur-nitrogen chain of 1,7-bis(trimethylsilyl)-1,3,5,7-tetraaza-2,4,6-trithia-1,2,5,6-heptatetraene takes place.

Azetidine derivatives

Novel azetidine derivatives of the formula STR1 wherein R1 is an acylamido group, R2 is selected from the group consisting of STR2 wherein R4, R5 and R6 are individually selected from the group consisting of hydrogen, lower alkyl and lower alkenyl, n is 2 or 3 and -- in the case when formula IIB is a phenyl - this group may carry one to four substituents selected from the group consisting of halogen, lower alkyl, lower alkenyl and phenyl, and R3 is lower alkyl optionally substituted with 1 or 2 phenyls which phenyl groups may be substituted with nitro and the dotted lines of formula IIB indicate the optional presence of double bonds and a process for their preparation and process for the preparation of cephalosporanic acid derivatives using the azetidines of formula I as intermediates.