120419-97-8

Basic information

• Product Name: Silanamine, 1,1,1-trimethyl-N-(phenylmethylene)-, (E)-
• CAS NO: 120419-97-8
• Molecular Formula: C10H15NSi
• Molecular Weight: 177.321
• Mol File: 120419-97-8.mol

Chemical Properties

• CAS DataBase Reference: Silanamine, 1,1,1-trimethyl-N-(phenylmethylene)-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Silanamine, 1,1,1-trimethyl-N-(phenylmethylene)-, (E)-(120419-97-8)
• EPA Substance Registry System: Silanamine, 1,1,1-trimethyl-N-(phenylmethylene)-, (E)-(120419-97-8)

Safety Data

• Hazardous Substances Data: 120419-97-8(Hazardous Substances Data)

Upstream product

• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 100-52-7 benzaldehyde 
• 4039-32-1 lithium hexamethyldisilazane 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 15500-60-4 N,N-bis(trimethylsilyl)formamide 
• 591-51-5 phenyllithium 

Downstream Products

• 61501-03-9 α-n-butylbenzylamine 
• 105370-59-0 (R)-α-butylbenzenemethanamine 
• 105370-60-3 (1S)-1-amino-1-phenylpentane 
• 134905-67-2 trans-3--4-phenyl-2-azetidinone 
• 5661-55-2 4-phenylazetidin-2-one 
• 121910-44-9 1-(4-Methylphenyl)-2-trimethylsilyloxy-4-phenyl-1,3-diaza-1,3-butadiene 
• 121910-47-2 C₁₇H₁₉ClN₂OSi 
• 141-05-9 Diethyl maleate 
• 172095-46-4 1-phenyl-3-trimethylsilyloxy-2-aza-1,3,5-hexatriene 
• 172095-47-5 (1E,3Z)-1,4-diphenyl-3-trimethylsilyloxy-2-aza-1,3-butadiene 
• 7486-93-3 3,3-dimethyl-4-phenylazetidin-2-one 
• 73845-05-3 (E)-N-benzylidenemethanesulfonamide 
• 179743-16-9 (1Z,3E)-1-phthalimido-2-(trimethylsilyl)oxy-3-aza-4-phenyl-1,3-butadiene 

Relevant articles and documents

Lewis acid-catalyzed electrocyclization of 2-aza-1,3-butadienes to NH-β-lactams

Lewis acid-catalyzed cyclization of 2-aza-3-trimethylsilyloxy-buta-1,3-diene is reported. Stereochemical differences with the uncatalyzed cyclization are discussed.

Catalytic enantioselective one-pot aminoborylation of aldehydes: A strategy for construction of nonracemic α-amino boronates

We report a strategy for the conversion of aldehydes to enantiomerically enriched α-amino boronates through the intermediacy of in situ-generated silylimines. This transformation is brought about by Pt-catalyzed asymmetric addition of B2(pin)s

Enantioselective addition of β-functionalized allylboronates to aldehydes and aldimines. Stereocontrolled synthesis of α-methylene-γ-lactones and lactams

We report results regarding the development of condensations of chiral β-alkoxycarbonylallylboronates on aldehydes and imines. These allylboronates add in a highly enantioselective and diastereospecific manner to afford biologically and synthetically useful chiral α-methylene-γ-butyrolactones and lactams. The nature of the electrophile (aldehyde vs imine) is shown to have a dramatic influence on the mechanism of the reaction, probably directing the stereoselectivity of the process through different transition states.

Synthesis of Venlafaxine from azadiene via a Hetero-Diels-Alder approach: New microwave-assisted transketalization and hydroxymethylation reactions

Hetero-Diels-Alder (HDA) methodology has been applied to the synthesis of Venlafaxine taking advantage of a novel MW-assisted transketalization and hydroxymethylation reaction.

Asymmetric allylboration of acyl imines catalyzed by chiral diols

Chiral BINOL-derived diols catalyze the enantioselective asymmetric allylboration of acyl imines. The reaction requires 15 mol % (S)-3,3′-Ph2-BINOL as the catalyst and allyldiisopropoxyborane as the nucleophile. The reaction products are obtained in good yields (75-94%) and high enantiomeric ratios (95:5-99.5:0.5) for aromatic and aliphatic imines. High diastereoselectivities (diastereomeric ratio > 98:2) and enantioselectivities (enantiomeric ratio > 98:2) are obtained in the reactions of acyl imines with crotyldiisopropoxyboranes. This asymmetric transformation is directly applied to the synthesis of Maraviroc, the selective CCR5 antagonist with potent activity against HIV-1 infection. Mechanistic investigations of the allylboration reaction including IR, NMR, and mass spectrometry studies indicate that acyclic boronates are activated by chiral diols via exchange of one of the boronate alkoxy groups with activation of the acyl imine via hydrogen bonding.

EuFOD-catalyzed Hetero-Diels-Alder (HDA) reaction under microwave heating

An efficient EuFOD-catalyzed hetero-Diels-Alder reaction between azadienes and aldehydes under microwave irradiation is reported. The reaction proceeds under microwave heating with 5 mol% of EuFOD in 45-83% yields. Georg Thieme Verlag Stuttgart.

Beta-lactam synthesis

The present invention is directed to a process for the preparation of β-lactams. Generally, an imine is cyclocondensed with a ketene acetal or enolate to form the β-lactam product in a "one pot" synthesis, this process is generally performed at a higher temperature than conventional processes.

Highly diastereoselective and enantioselective preparation of homoallylic amines: Application for the synthesis of β-amino acids and γ-lactams

Reactions of N-silyl- and N-aluminoimines with B- allyldiisopinocampheylborane in the presence of methanol, followed by oxidative workup furnished homoallylic amines in good yields and high ee. A 11B NMR spectroscopy study revealed that the reactions do not proceed, even at room temperature, unless a molar equivalent of water or methanol is added. The first reagent-controlled asymmetric crotylboration and alkoxyallylboration of aldimines furnishing β-methyl or βalkoxy homoallylic amines in very high diastereoselectivity and enantioselectivity are reported herein. Crotylboration and alkoxyallylboration of imines proceed only with the "allyl"-boron "ate" complexes, instead of the "allyl"-dialkylboron reagents used with aldehydes. The addition of methanol is necessary for these reactions as well. Application of this methodology for the conversion of representative nitriles to β-amino acids in two steps has been described. Additionally, a procedure for the preparation of chiral δ-amino alcohols and γ-lactams from nitriles is also reported.

Isoprene-catalyzed lithiation of imidazole: Synthesis of 2-(hydroxyalkyl)- and 2-(aminoalkyl)imidazoles

2-Lithioimidazole was prepared by means of a new protocol, which consists of a slight excess of lithium metal in the presence of a substoichiometric amount of isoprene (20 mol%) in THF at room temperature. By reacting this organolithium with carbonyl elec

Direct Synthesis of Functionalized Pyrrole Derivatives from Aldehydes, Bis(trimethylsilyl)amide and Methoxyallene

In situ generation of N-trimethylsilylated imines from aldehydes and lithium bis(trimethylsilyl)amide and subsequent treatment with lithiated methoxyallene afforded after warm up of the mixture to room temperature the corresponding 3-methoxy substituted dihydropyrrole derivatives like 7. Boc-protection at the pyrrole nitrogen could smoothly be included into the reaction sequence, leading to compounds such as 8, 10, 11, and 13. This direct generation of functionalized and N-protected pyrrole derivatives proceeds particularly well when N-methylpyrrole-2-carbaldehyde (14) was the starting material which furnished compounds 16 to 19 in very good yields. The corresponding reaction conditions for aliphatic aldehydes require optimization; dihydropyrroles 20 and 21 were obtained only in low yields.