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Product Details of [ 25357-81-7 ]

CAS No. :25357-81-7 MDL No. :MFCD00054848
Formula : C12H35NO3Si4 Boiling Point : -
Linear Structure Formula :- InChI Key :KCJAIHQXOQUWTI-UHFFFAOYSA-N
M.W : 353.75 Pubchem ID :2756547
Synonyms :

Safety of [ 25357-81-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 25357-81-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 25357-81-7 ]

[ 25357-81-7 ] Synthesis Path-Downstream   1~30

  • 1
  • [ 1066-40-6 ]
  • [ 919-30-2 ]
  • [ 25357-81-7 ]
YieldReaction ConditionsOperation in experiment
88% Heating;
  • 2
  • [ 1066-40-6 ]
  • [ 146629-21-2 ]
  • [ 25357-81-7 ]
YieldReaction ConditionsOperation in experiment
Heating;
YieldReaction ConditionsOperation in experiment
3-Trimethoxysilyl-propylamin, Bis-(trimethylsilyl)-oxid/ Δ;
Trimethoxysilylamin, Bis-trimethylsilyloxid;
γ-NH2-(CH2)3Si(OC2H5)3, Hexamethyldisiloxan;
Illustrative of such aminosilanes are: ... gamma-aminopropyldimethylethoxysilane gamma-aminopropyldiethylmethylsilane gamma-aminopropyl-tris(trimethylsiloxy)silane ω-aminoundecyltrimethoxysilane ...
Suitable tris(trimethylsiloxy)silylalkyl amines for use in the preparation of the dyestuufs of the invention include the following: 3-tris(trimethylsiloxy)silylpropylamine N-methyl-3-tris(trimethylsiloxy)silylpropylamine N-ethyl-3-tris(trimethylsiloxy)silylpropylamine N-propyl-3-tris(trimethylsiloxy)silylpropylamine N-isopropyl-3-tris(trimethylsiloxy)silylpropylamine N-butyl-3-tris(trimethylsiloxy)silylpropylamine 2-tris(trimethylsiloxy)silylethylamine N-methyl-2-tris(trimethylsiloxy)silylethylamine N-ethyl-2-tris(trimethylsiloxy)silylethylamine ...
1 Example 1 Example 1 Synthesis of 3-(chloroacetylamido)propyltris(trimethylsiloxysilane). To a vigorously stirred, biphasic solution of 3-aminopropyltris(trimethylsiloxy)silane (50 g, 141 mmol) obtained from Gelest, Inc., Morrisville, Pa., in dichloromethane (200 mL) and NaOH(aq) (0.75 M, 245 mL) was added a solution of chloroacetyl chloride (14.6 mL, 0.18 mol) in dichloromethane (80 mL) dropwise at ambient temperature. After 1 additional hour at ambient temperature, the organic layer was separated and stirred 3 h over silica gel (15 g) and an additional half hour over sodium sulfate (15 g).
3-Trimethoxysilyl-propylamin, Me4NOH, Me3Si-O-SiMe3;

  • 4
  • [ 25357-81-7 ]
  • [ 2170-03-8 ]
  • [ 1000579-23-6 ]
YieldReaction ConditionsOperation in experiment
In chloroform at 0 - 20℃; for 15h; 1 Example 1. Synthesis of carboxylic siloxanyl monomer.; This method is adapted from a literature procedure: Zilkha, A and Golik, U. J. Org. Chem. 1963, 28, 2007-2009. To a stirred solution of itaconic anhydride (4.24 g, 37.8 mmol) in CHCl3 (40 mL) is slowly added 3-aminopropyltris(trimethylsiloxy)silane (15.1 mL, 38.0 mmol) at 0 0C under a nitrogen atmosphere. The cooling bath is removed and the solution allowed to warm to ambient temperature and stirred under a nitrogen atmosphere an additional 15 h. Following removal of solvent at reduced pressure, the viscous, clear oil is analyzed via mass spectrometry to confirm the presence of the proposed structure.
  • 5
  • [ 25357-81-7 ]
  • [ 14199-15-6 ]
  • [ 67-56-1 ]
  • C20H41NO5Si4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 70℃; for 12h; Neat (no solvent); Heating / reflux; 11 Example 11 Lipase (N435) was used to catalyze the reaction of 3- [AMINOPROPYLTRIS (TRIMETHYL-SILOXY) SILANE] and phenyl acetic acid methyl ester as shown in the following diagram: OH N435 O [ (CH3) 3Si SiNL 13'NH2 + O neat 0 70°c 12 hours ou Oh O [ (CH3) 3Siz i ? Si4NHw + CH30H H The reaction was conducted with constant stirring (i. e. , magnetic stir bar) in a two-neck round-bottom flask attached to a Dean-Stark trap and a water-cooled condenser in a heated oil bath. The reaction was formulated with a [ORGANOSILICON] : organic mole ratio equal to 1: 1. The enzyme: monomer weight ratio was 1: 10. The phenyl acetic acid methyl ester was added to 3- [AMINOPROPYLTRIS (TRIMETHYL-SILOXY) SILANE] at [70°C.] After homogenization, dried lipase enzyme was added to the reaction mixture and heated for 12 hours. The reaction was monitored by TLC. After 12 hours, chloroform was added to the mixture to remove the contents from the flask and filter out the enzyme. Subsequently, the filtrate was evaporated on a rotary evaporator and dried in a vacuum oven overnight [AT ~45°C] in order to isolate the product. The material was characterized [BY 1H] and [13C] NMR as well as FTIR. Fig. 11 illustrates the 1H NMR of the amidation. Based on the spectral data, N435 was observed to catalyze the formation of the amide bond.
  • 6
  • [ 46117-43-5 ]
  • [ 25357-81-7 ]
  • N-vinyloxycarbonyl-3-aminopropyl-tris(trimethylsiloxysilane) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: vinyl phenyl carbonate; (3-aminopropyl)tris(trimethylsiloxy)silane In tetrahydrofuran at 30℃; for 6h; Stage #2: With 1,6-Hexanediamine In tetrahydrofuran at 60℃; for 48h;
  • 7
  • [ 46117-43-5 ]
  • [ 25357-81-7 ]
  • N-vinyloxycarbonyl-3-aminopropyl-tris(trimethylsiloxysilane) [ No CAS ]
  • 3-[tris(trimethylsiloxy)silyl]propyl phenyl carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran at 50℃; for 1h;
  • 8
  • hexamethylene diamine [ No CAS ]
  • [ 46117-43-5 ]
  • [ 25357-81-7 ]
  • N-vinyloxycarbonyl-3-aminopropyl-tris(trimethylsiloxysilane) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran 5 Synthesis of 3-[Tris(trimethylsiloxy)silyl]propyl Vinyl Carbamate EXAMPLE 5 Synthesis of 3-[Tris(trimethylsiloxy)silyl]propyl Vinyl Carbamate To a solution of 3-aminopropyltris(trimethylsiloxy)-silane in THF is added vinylphenylcarbonate, with a mild exotherm being observed. The solution is heated to 30° for a minimum of 6 hours. Reaction progress is monitored by G.C. Hexamethylene diamine is added to the reaction mixture, and the temperature raised to 60° for a minimum of 48 hours. Reaction progress is again monitored by G.C. The solvent is removed under reduced pressure, and the residue taken back up in hexanes. The solution is washed with 2N NaOH, 2N HCl, then saturated NaHCO3 solution, and dried with magnesium sulfate. The solvent is removed under reduced pressure and the crude product is purified.
  • 9
  • [ 25357-81-7 ]
  • [ 79-04-9 ]
  • [ 942207-52-5 ]
YieldReaction ConditionsOperation in experiment
84% With sodium hydroxide In dichloromethane; water at 20℃; for 4h; 1 Preparation of 3-(chloroacetylamido)propyltris(trimethylsiloxysilane) To a vigorously stirred, biphasic solution of 3-aminopropyltris(trimethylsiloxy)silane (50 g, 141 mmol) obtained from Gelest, Inc., Morrisville, Pa., in dichloromethane (200 mL) and NaOH(aq) (0.75 M, 245 mL) was added a solution of chloroacetyl chloride (14.6 mL, 0.18 mol) in dichloromethane (80 mL) dropwise at ambient temperature. After 1 additional hour at ambient temperature, the organic layer was separated and stirred 3 h over silica gel (15 g) and an additional half hour over sodium sulfate (15 g). Solvents were removed at reduced pressure to afford the product as a colorless liquid (42 g, 84%): 1H NMR (CDCl3, 400 MHz) δ 6.64 (br, 1 H), 4.04 (s, 2 H), 3.30-3.24 (m, 2 H), 1.59-1.51 (m, 2 H), 0.45-0.42 (m, 2 H), 0.08 (s, 27 H); GC: 99.3% purity; ESI-TOF MS data is summarized in Table 1, and the mass spectrum also illustrated the characteristic chlorine isotopic distribution pattern as predicted by the elemental composition.
  • 10
  • [ 25357-81-7 ]
  • [ 74-88-4 ]
  • [ 1259287-99-4 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In N,N-dimethyl-formamide at 20℃; for 3h; 7.1 0.8 g of 3-aminopropyltris(trimethylsiloxy)silane, 1.8 g of methyl iodide and 1.35 g of sodium carbonate are added to 50 ml of dimethylformamide. The reaction mixture is stirred for 3 hours at room temperature. The solvent is evaporated and the residue taken in methylene chloride and water. The organic phase is then washed with water, dried and evaporated whereby compound (35) is obtained; 1H-NMR (ppm, CDCI3): 3.45-3.32 11 H m, 1.68-1.58 2H m, 0.39 2H t, 0.00 27H s.
  • 11
  • 3-iodopropyltris(trimethylsiloxy)silane [ No CAS ]
  • [ 25357-81-7 ]
  • [ 1259287-97-2 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In ISOPROPYLAMIDE at 80℃; for 15h; 6.2 14.3 g of 3-iodopropyltris(trimethylsiloxy)silane (28), 5.7 g of 3-aminopropyltris(trimethyl- siloxy)silane and 9.6 g of sodium carbonate are added to 50 ml dimethylacetamide and stirred for 15 hours at 800C. The dimethylacetamide is then evaporated and the residue taken up in methylene chloride. The organic phase is washed with water, dried and evaporated. The product is purified by column chromatography on silica gel to give 7 g of a slightly yellowish oil of formula (30); 1H-NMR (ppm, CDCI3): 2.21 6H t, 1.38 6H txt, 0.28 6H t,0 81 H s.
  • 12
  • [ 2680-03-7 ]
  • [ 25357-81-7 ]
  • [ 212374-56-6 ]
YieldReaction ConditionsOperation in experiment
4.21 g In ethanol at 20℃; for 96h;
  • 13
  • [ 25357-81-7 ]
  • [ 556-52-5 ]
  • [ 1334704-48-1 ]
YieldReaction ConditionsOperation in experiment
at 30℃; for 20h; 19 Synthesis Example 19 3-Aminopropyltris(trimethylsiloxy)silane (49 g, 0.14 mol) was placed in a 3-necked flask and a reflex condenser, thermometer, and dropping funnel were attached. Glycidol (2,3-epoxy-l- propanol, 3.5 g, 0.05 mol) was added to the dropping funnel, and added by drops over approximately 40 minutes while mixing at 30°C. A GC measurement was performed each hour starting at the time that dropwise addition was completed in order to confirm the progress of the reaction. 20 hours after dropwise addition was completed it was confirmed that the glycidol peak was 1% or less and the reaction was terminated. The solution was concentrated in an evaporator, and then purified by reduced pressure installation (full vac, bp 190°C). The yield was 13.65 g (67.8% yield), and the GC purity was 92.8%.
  • 14
  • [ 25357-81-7 ]
  • C18H43NO6Si4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 20 h / 30 °C 2: saccharin / 2 h / 100 °C 3: triethylamine / ethyl acetate / 2 h / -2 - 3 °C 4: acetic acid; methanol / 4 h / 40 °C
  • 15
  • [ 25357-81-7 ]
  • [ 1334704-49-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 20 h / 30 °C 2: saccharin / 2 h / 100 °C
  • 16
  • [ 25357-81-7 ]
  • [ 1334704-50-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 20 h / 30 °C 2: saccharin / 2 h / 100 °C 3: triethylamine / ethyl acetate / 2 h / -2 - 3 °C
  • 17
  • [ 25357-81-7 ]
  • [ 13818-44-5 ]
  • [ 1384895-95-7 ]
YieldReaction ConditionsOperation in experiment
for 26.0h; Example 3; 3-([2-hydroxy-3-(methacryloyloxy)propoxy]carbonyl> amino)propyltris(trimethylsiloxy)silane; 3-Aminopropyl tris(trimethylsiloxy) silane (1 .9 g, 5.4 mmol) was added dropwise to stirred <strong>[13818-44-5]GCMA</strong> (1 .0 g, 5.4 mmol). The reaction mixture was stirred for 26 h and monitored by IR spectroscopy. The samples at 20.5 h and 26 h were identical, suggesting that the reaction had stopped, however a small carbonate signal (1802 cm"1) suggested that some unreacted <strong>[13818-44-5]GCMA</strong> was still present.A few drops of 3-aminopropyl tris(trimethylsiloxy) silane were added and the reaction mixture stirred until the C=0 carbonate signal was reduced. The reaction product was obtained as a colourless oil (1 .27 g, 43%).IR: (cm 1) 3375 (OH), 2958 (CH), 1718 (C=0 ester and urethane), 1532 (amide II), 1250 (Si-Me), 1018 (Si-O) and 836 (Si-Me).1H-NMR (C2HCI3, 400 MHz) 0.09 (s, SiCH3), 0.41 - 0.45 (2 H, m SiCH2), 1.48 - 1 .56 (2 H, m, SiCH2CW2), 1 94 (3 H, s, CCH3), 3.12 - 3.17 (2 H, m CH2NH), 3.72 - 5.06 (5 H, m, 2 x CH2O and CHOH)5.58 - 5.59 (1 H, m, one of C=CH2) and 6.12 - 6.16 (1 H, m, one of C=CH2).Inspection of the spectra suggested that the reaction had been successful and that the product is present as a mixture of isomers. It also appeared that some Michael addition had occurred, as judged by small signals at 1.2 and 2.5 - 3.0 ppm.
  • 18
  • [ 25357-81-7 ]
  • [ 814-68-6 ]
  • [ 115258-10-1 ]
YieldReaction ConditionsOperation in experiment
92% With sodium carbonate In water 1 In a 100 mL three-necked flask equipped with a thermometer, a dropping funnel and a nitrogen inflow instrument, and a magnetic stirring bar therein, were put 1 mole of [(CH3)3SiO]3Si(CH2)3NH2, 1.05 moles of acrylic acid chloride and 2.0 moles of sodium carbonate in an aqueous 10% solution and stirred. Subsequently, the mixture was washed with water, filtrated through a paper filter and, then, volatile materials were distilled off under a reduced pressure to obtain a colorless product which was solid at room temperature and had a melting point of 51 degrees C. A molecular structure of the product obtained was analyzed by 1H-NMR and IR to find that the product was a silicone compound represented by the following formula. The yield was 92%. The 1H-NMR spectra and IR spectra are as described below. [0080] 1H-NMR (400 MHz, CDCl3): δ 0.09 (s, 27H), 0.45-0.50 (m, 2H), 1.59 (quin., J=7.0 Hz, 2H), 3.32 (q, J=7.0 Hz, 2H), 5.58 (brs, 1H), 5.62 (dd, J=10.3, 1.4 Hz, 1H), 6.06 (ddd, 17.0, 8.4, 1.4 Hz, 1H), 6.25 (dd, 17.0, 10.3 Hz, 1H) [0081] IR(ATR): ν 753, 835, 1041, 1248, 1408, 1556, 1625, 1655, 2958, 3285.
  • 19
  • [ 25357-81-7 ]
  • C33H95NO11Si13 [ No CAS ]
  • [ 347165-20-2 ]
  • C66H168N6O20Si21 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: 1,3,5-benzenetricarbonyl triazide at 100℃; Reflux; Stage #2: (3-aminopropyl)tris(trimethylsiloxy)silane; C33H95NO11Si13 In toluene Compound C. Mixed benzene trisurea Compound C. Mixed benzene trisurea (0067) (0068) Compound C, a mixed benzene trisurea, was prepared according to the procedure described for Compound A using sodium azide (1.763 g, 27.119 mmol, 7.2 equiv.) dissolved in 10 mL of deionized water and cooled to 0° C., 1,3,5-benzenetricarbonyl chloride (1.0031 g, 3.778 mmol, 1 equiv.) dissolved in 10 mL of THF and cooled to 0° C. and a mixture containing a 2:1 molar ratio of aminopropyltris(trimethylsiloxy)silane (2.665 g, 7.532 mmol, 1.99 equiv.) to H2N(CH2)3Si(CH3)2(OSi(CH3)2)11Si(CH3)2(CH2CH2CH2CH3) (3.975 g, 3.792 mmol, 1.00 equiv.). The product was isolated as a waxy white solid (6.385 g, 3.262 mmol, 87% yield). 1H NMR (CD3OD, 400.13 MHz) δ (ppm): 7.12 (s, 2.8H, HAr), 3.17 (broad t, 6.0H, J=7.0 Hz, NCH2), 1.58 (broad mult, 6.4H, NCH2CH2), 1.37 (broad mult, 4.8H, SiCH2CH2CH2CH3), 0.93 (broad t, 3.0H, J=6.3 Hz, SiCH2CH2CH2CH3), 0.70 to 0.45 (overlapping broad mult, 8.2H, SiCH2), 0.35 to -0.30 (130.6H, SiMe). 13C NMR (CD3OD, 150.72 MHz) δ (ppm): 156.79, 140.35, 103.85, 42.42, 42.12, 26.07, 25.28, 24.03, 23.81, 17.55, 14.89, 12.83, 11.27, 0.51, 0.07, -0.97.
  • 20
  • [ 25357-81-7 ]
  • [ 347165-20-2 ]
  • benzene-1,3,5-tris(tris(trimethylsiloxy)silylpropylurea) [ No CAS ]
YieldReaction ConditionsOperation in experiment
3.291 g Stage #1: 1,3,5-benzenetricarbonyl triazide at 100℃; Reflux; Stage #2: (3-aminopropyl)tris(trimethylsiloxy)silane In toluene Compound A. Benzene-1,3,5-tris(tris(trimethylsiloxy)silylpropylurea) Compound A. Benzene-1,3,5-tris(tris(trimethylsiloxy)silylpropylurea) (0060) (0061) Sodium azide (1.75 g, 26.919 mmol, 7 equiv.) was dissolved in 10 mL of deionized water and cooled to 0° C. Separately, 1,3,5-benzenetricarbonyl chloride (1.006 g, 3.789 mmol, 1 equiv.) was dissolved in 10 mL of tetrahydrofuron (THF) and cooled to 0° C. The acid chloride solution was added to the stirring sodium azide solution resulting in the formation of 1,3,5-benzenetricarbonyl azide as a white precipitate. The mixture was stirred at 0° C. for 2 hours behind a blast shield at which point 200 mL of cold toluene and 10 mL of water were added to dissolve all solids. The toluene layer was isolated, washed with water (3×80 mL), saturated aqueous brine (80 mL), dried over magnesium sulfate (MgSO4) and filtered. The filtrate was collected and transferred to a round bottom flask fitted with a reflux condenser connected to a nitrogen inlet and heated to 100° C. for several hours until gas evolution (N2 extrusion) ceased. The solution was then removed from the oil bath and aminopropyltris(trimethylsiloxy)silane (4.022 g, 11.369 mmol, 3.00 equiv.) was added to the hot toluene solution and stirred vigorously overnight. As the mixture cooled to room temperature, it became hazy and the viscosity of the solution increased. The volatiles were then removed under vacuum to produce the intended product as a pale yellow solid (3.291 g, 2.607 mmol, 69% yield). 1H NMR (CDCl3, 400.13 MHz) δ (ppm): 8.24 (broad s, 0.5H, NH), 8.72 (broad s, 3.4H, HAr), 5.38 (broad s, 0.6H, NH), 3.15 (broad s, 4.9H, NHCH2), 1.55 (broad s, 9.0H, CH2CH2Si), 0.46 (broad s, 6.0H, CH2Si), 0.30 to -0.15 (84.0H, SiMe). 13C NMR (CDCl3, 100.62 MHz) δ (ppm): 43.20, 24.25, 11.95, 1.85, 1.74. (0062) Solubility in CO2 and thickening efficacy of Compound A was assessed and the results are shown in Tables 1 and 2 below. As used herein, the term “cloud point” refers to the pressure at which the material begins to precipitate from an optically transparent solution in dense CO2 at a given temperature to form a cloudy, optically opaque mixture. [table-us-00001-en] TABLE 1 Cloud Point for Compound A. Amount of Co- Pressure/ Compound Solvent CO2 Temperature 1.6 wt. % 48.4 wt. % 50 wt. % 1280 psi 25° C.; hexanes 2200 psi 70° C. 1.3 wt. % 38.7 wt. % 60 wt. % 8800 psi 25° C.; hexanes 6100 psi 74° C. 0.5 wt. % 39.5 wt. % 60 wt. % >800 psi hexanes 0.1 wt. % 25 wt. % 74.9 wt. % FontWeight="Bold" FontSize="10" Insoluble up to 80° C. hexanes 0.1 wt. % - 99.9 wt. % FontWeight="Bold" FontSize="10" Insoluble [table-us-00002-en] TABLE 2 Viscosity Effects of Compound A. Amount of Co- Pressure/ Viscosity Compound Solvent CO2 Temperature 320X increase 1.6 wt. % 48.4 wt. % 50 wt. % 25° C. hexanes 100X increase 1.3 wt. % 38.7 wt. % 60 wt. % 25° C. hexanes 14.4X increase 0.5 wt. % 39.5 wt. % 60 wt. % 25° C. hexanes and 8000 psi 12.8X increase 0.5 wt. % 39.5 wt. % 60 wt. % 25° C. hexanes and 6000 psi (0063) Compound A is also soluble in NGLs and increases the viscosity of NGLs. For example, the cloud point for 1.5 wt. % of Compound A in 98.5 wt. % butane was at 192 psi at 80° C., with 2× increase in viscosity; at 154 psi at 60°, with 10× increase; at 124 psi at 40° C., with 50× increase; and at 65 psi at 25° C., with 300× increase in viscosity.
  • 21
  • [ 25357-81-7 ]
  • [ 87781-93-9 ]
  • C17H37N5O4Si4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In methanol at 90℃; 2 To a solution of 2-bromohypoxanthine (Aldrich, 10.0 g, 46.5 mmol) in methanol (200 mL) is added (3-aminopropyl)tris(trimethylsiloxy)silane (Aldrich, 32.90 g, 93.0 mmol) and diisopropylethylamine (20.2 mL, 116.3 mmol). The reaction is stirred at 90° C. overnight. The reaction may be represented by: The solvent is removed by rotary evaporation and the remaining fluid is collected. The fluid is purified by column chromatography using methylene chloride: methanol (98:2) on silica which separated the remaining (3-aminopropyl)tris (trimethylsiloxy)silane and the desired product. The desired product comprises a functionalized low energy compound comprising silicone and a terminal reactive group.
  • 22
  • [ 25357-81-7 ]
  • C36H36N4O6 [ No CAS ]
  • C46H69N5O8Si4 [ No CAS ]
  • C58H102N6O10Si8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane at 20℃; Darkness; Overall yield = 87 percent; Overall yield = 0.3081 g; Compound 14-mix (Ce6-mix-T(TMS)SP1517 amide) To compound 1 (0.201 g, 0.323 mmol) in DCM (20 mL was added (3- aminopropyl)tris(trimethylsiloxy)silane (0.228 g, 0.645 mmol). After stirring at room temperature in the absence of light overnight, solvent and volatiles were removed in vacuo , the residue was dissolved in hexane (20 mL filtered, evaporated and dried in vacuo. 14-mix was obtained as a mixture of compound 14-mono (Ce6-mono-T(TMS)SP15 amide) and 14- bis (Ce6-bis-T(TMS)SP15’17 amide) (0.3081 g, 87% yield). Ce6-mono-T(TMS)SP15 amide, MS-ESI (HRMS) m/z calculated for C46 H70 N5 08 Si4 (M+H+): 932.4296. Found: 932.4288. (0783) Ce6-bis-T(TMS)SP15’17 amide, MS-ESI (HRMS) m/z calculated for C58 H103 N6 O10 Si8, (M+H+): 1267.5884. Found: 1267.5876.
  • 23
  • [ 1072-09-9 ]
  • [ 25357-81-7 ]
  • 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)hexanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% In toluene for 24h; Dean-Stark; Reflux; 1a Synthesis of 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)hexanamide (Surfactant 1) and 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N-dimethyl-6-oxohexan-1-aminium salt (Surfactant 2) 6-(Dimethylamino)hexanoic acid (2.00 g, 12.56 mmol, 1 equiv.) was dissolved in toluene (50 mL) in a 100 mL round bottom boiling flask equipped with a Dean Stark trap, then 3-aminopropyltris(trimethylsiloxy)silane (5.48 mL, 13.81 mmol, 1.1 equiv.) was added. The reaction vessel was heated, and the reaction refluxed for 24 hours until no more water separated in the Dean Stark tube. The solvent was removed under vacuum to give Surfactant 1 as a yellow oil in 94% yield. 1H NMR (500 MHz, DMSO) δ: 0.09 (s, 27H), 0.28-0.31 (m, 2H), 1.12-1.26 (m, 2H), 1.27-1.30 (m, 4H), 1.38-1.41 (m, 2H), 1.94 (t, J=7.3 Hz, 2H), 2.00 (s, 6H), 2.06-2.03 (m, 2H), 2.89 (dd, J=12.9, 6.8 Hz, 2H).
94% In toluene for 24h; Dean-Stark; Reflux; 1a Synthesis of 6-(dimethylamino)-N-(3-( 1 1 1 5.5.5-hexamethyl-3- ((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)hexanamide (Surfactant 1 ) and 6-((3- (1 1 1 .5.5.5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-N. N- dimethyl-6-oxohexan-1-aminium salt (Surfactant 2) 6-(Dimethylamino)hexanoic acid (2.00 g, 12.56 mmol, 1 equiv.) was dissolved in toluene (50 ml_) in a 100 ml_ round bottom boiling flask equipped with a Dean Stark trap, then 3-aminopropyltris(trimethylsiloxy)silane (5.48 ml_, 13.81 mmol, 1.1 equiv.) was added. The reaction vessel was heated, and the reaction refluxed for 24 hours until no more water separated in the Dean Stark tube. The solvent was removed under vacuum to give Surfactant 1 as a yellow oil in 94% yield. 1H NMR (500 MHz, DMSO) 5: 0.09 (s, 27H), 0.28-0.31 (m, 2H), 1.12-1.26 (m, 2H), 1 .27-1.30 (m, 4H), 1.38-1 .41 (m, 2H), 1 .94 (t, J = 7.3 Hz, 2H), 2.00 (s, 6H), 2.06 - 2.03 (m, 2H), 2.89 (dd, J = 12.9, 6.8 Hz, 2H).
94% In toluene for 24h; Dean-Stark; Reflux; 1a Synthesis of 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3- ((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)hexanamide (Surfactant 1) and 6-((3- (1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N- dimethyl-6-oxohexan-1-aminium salt (Surfactant 2) 6-(Dimethylamino)hexanoic acid (2.00 g, 12.56 mmol, 1 equiv.) was dissolved in toluene (50 mL) in a 100 mL round bottom boiling flask equipped with a Dean Stark trap, then 3-aminopropyltris(trimethylsiloxy)silane (5.48 mL, 13.81 mmol, 1.1 equiv.) was added. The reaction vessel was heated, and the reaction refluxed for 24 hours until no more water separated in the Dean Stark tube. The solvent was removed under vacuum to give Surfactant 1 as a yellow oil in 94% yield.1H NMR (500 MHz, DMSO) : 0.09 (s, 27H), 0.28-0.31 (m, 2H), 1.12-1.26 (m, 2H), 1.27-1.30 (m, 4H), 1.38-1.41 (m, 2H), 1.94 (t, J = 7.3 Hz, 2H), 2.00 (s, 6H), 2.06 - 2.03 (m, 2H), 2.89 (dd, J = 12.9, 6.8 Hz, 2H).
94% In toluene for 24h; Dean-Stark; Reflux; 1a Synthesis of 6-(dimethylamino)-N-(3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilypoxy)trisiloxan-3-yl)propyl)hexanamide (Surfactant 1) and 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilypoxy)trisiloxan-3-yl)propyl)amino)-N,N-dimethyl-6-oxohexan-1-aminium Salt (Surfactant 2) 6-(Dimethylamino)hexanoic acid (2.00 g, 12.56 mmol, 1 equiv.) was dissolved in toluene (50 mL) in a 100 mL round bottom boiling flask equipped with a Dean Stark trap, then 3-aminopropyltris(trimethylsiloxy)silane (5.48 mL, 13.81 mmol, 1.1 equiv.) was added. The reaction vessel was heated, and the reaction refluxed for 24 hours until no more water separated in the Dean Stark tube. The solvent was removed under vacuum to give Surfactant 1 as a yellow oil in 94% yield. 1H NMR (500 MHz, DMSO) δ: 0.09 (s, 27H), 0.28-0.31 (m, 2H), 1.12-1.26 (m, 2H), 1.27-1.30 (m, 4H), 1.38-1.41 (m, 2H), 1.94 (t, J=7.3 Hz, 2H), 2.00 (s, 6H), 2.06-2.03 (m, 2H), 2.89 (dd, J=12.9, 6.8 Hz, 2H).
94% In toluene for 24h; Reflux; Dean-Stark; 1a Synthesis of 6-(dimethylamino)-N-(3-(1 ,1 ,1 ,5,5,5-hexamethyl-3- ((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)hexanamide (Surfactant 1) and 6-((3- (1 ,1 ,1 ,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N- dimethyl-6-oxohexan-1-aminium salt (Surfactant 2) (2) 6-(Dimethylamino)hexanoic acid (2.00 g, 12.56 mmol, 1 equiv.) was dissolved in toluene (50 ml_) in a 100 ml_ round bottom boiling flask equipped with a Dean Stark trap, then 3-aminopropyltris(trimethylsiloxy)silane (5.48 ml_, 13.81 mmol, 1.1 equiv.) was added. The reaction vessel was heated, and the reaction refluxed for 24 hours until no more water separated in the Dean Stark tube. The solvent was removed under vacuum to give Surfactant 1 as a yellow oil in 94% yield. 1H NMR (500 MHz, DMSO) δ: 0.09 (s, 27H), 0.28-0.31 (m, 2H), 1.12-1.26 (m, 2H), (0169) 1.27-1.30 (m, 4H), 1.38-1.41 (m, 2H), 1.94 (t, J = 7.3 Hz, 2H), 2.00 (s, 6H), 2.06 - 2.03 (m, 2H), 2.89 (dd, J = 12.9, 6.8 Hz, 2H).
94% In toluene for 24h; Dean-Stark; Reflux; 1a Example 1a: Synthesis of 6-(dimethylamino)-N-(3-(1 ,1 ,1 ,5,5,5-hexamethyl-3- ((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)hexanamide (Surfactant 1) and 6-((3- (1.1.1.5.5.5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-N.N- dimethyl-6-oxohexan-1-aminium salt (Surfactant 2) 6-(Dimethylamino)hexanoic acid (2.00 g, 12.56 mmol, 1 equiv.) was dissolved in toluene (50 mL) in a 100 mL round bottom boiling flask equipped with a Dean Stark trap, then 3-aminopropyltris(trimethylsiloxy)silane (5.48 mL, 13.81 mmol, 1.1 equiv.) was added. The reaction vessel was heated, and the reaction refluxed for 24 hours until no more water separated in the Dean Stark tube. The solvent was removed under vacuum to give Surfactant 1 as a yellow oil in 94% yield. 1H NMR (500 MHz, DMSO) 5: 0.09 (s, 27H), 0.28-0.31 (m, 2H), 1.12-1.26 (m, 2H), 1.27-1.30 (m, 4H), 1.38-1.41 (m, 2H), 1.94 (t, J = 7.3 Hz, 2H), 2.00 (s, 6H), 2.06 - 2.03 (m, 2H), 2.89 (dd, J = 12.9, 6.8 Hz, 2H).

  • 24
  • [ 25357-81-7 ]
  • 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N,N-trimethyl-6-oxohexan-1-aminium iodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: toluene / 24 h / Dean-Stark; Reflux 2.1: sodium carbonate / acetonitrile / 0.17 h 2.2: 24 h / 40 °C
Multi-step reaction with 2 steps 1.1: toluene / 24 h / Dean-Stark; Reflux 2.1: sodium carbonate / acetonitrile / 0.17 h 2.2: 24 h / 40 °C
Multi-step reaction with 2 steps 1: toluene / 24 h / Reflux; Dean-Stark 2: sodium carbonate / acetonitrile / 24 h / 40 °C
Multi-step reaction with 2 steps 1: toluene / 24 h / Dean-Stark; Reflux 2: sodium carbonate / acetonitrile / 24 h / 40 °C

  • 25
  • [ 25357-81-7 ]
  • 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N-dimethyl-6-oxohexan-1-amine oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene / 24 h / Dean-Stark; Reflux 2: dihydrogen peroxide / water / 12 h / Reflux
Multi-step reaction with 2 steps 1: toluene / 24 h / Dean-Stark; Reflux 2: dihydrogen peroxide / water / 12 h / Reflux
Multi-step reaction with 2 steps 1: toluene / 24 h / Reflux; Dean-Stark 2: dihydrogen peroxide / water / 12 h / Reflux
Multi-step reaction with 2 steps 1: toluene / 24 h / Dean-Stark; Reflux 2: dihydrogen peroxide / water / 12 h / Reflux

  • 26
  • [ 25357-81-7 ]
  • 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N-dimethyl-6-oxohexan-1-aminium chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene / 24 h / Dean-Stark; Reflux 2: hydrogenchloride / water; toluene / pH 4 - 7
Multi-step reaction with 2 steps 1: toluene / 24 h / Dean-Stark; Reflux 2: hydrogenchloride / toluene
  • 27
  • [ 25357-81-7 ]
  • 6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-N,N-dimethyl-6-oxohexan-1-amine oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene / 24 h / Dean-Stark; Reflux 2: dihydrogen peroxide / water / 12 h / Reflux
  • 28
  • [ 25357-81-7 ]
  • 4-((6-((3-(1,1,1,5,5,5-hexamethyl-3-((trimethylsilyl)oxy)trisiloxan-3-yl)propyl)amino)-6-oxohexyl)dimethylammonio)butane-1-sulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene / 24 h / Dean-Stark; Reflux 2: ethyl acetate / 12 h / Reflux
  • 29
  • [ 25357-81-7 ]
  • [ 128-69-8 ]
  • C48H74N2O10Si8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% With 1H-imidazole; zinc diacetate at 140℃; for 24h; Inert atmosphere;
  • 30
  • [ 25357-81-7 ]
  • [ 530-62-1 ]
  • N-[3-tris(trimethylsiloxy)silylpropyl]-imidazole-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 72h; Inert atmosphere; To prepare Si-Glu-NH2, (3-imidazolecarboxamide) tris(trimethylsiloxy)silane was first synthesized according to the following protocol: (3-aminopropyl) tris(trimethylsiloxy)silane (1 eq, 5 mmol, 2 mL) was dissolved in dry DCM (8 mL) with DIEA (0.6 eq). CDI (1.1 eq) was dissolved in dry DCM (30 mL) and added onto the silane solution. The mixture was stirred at room temperature under argon for three days. The solvent was evaporated under vacuum and the resulting oil was precipitated in water before being lyophilized (93% yield). Then, isoglutamine (Si-Glu-NH2, 1 eq, 0.86 mmol, 126 mg) was dissolved in a mixture of water/acetonitrile (1/1v/v) and DIEA (5 eq) was added. (3-imidazolecarboxamide)tris(trimethylsiloxy)silane (1.1 eq) was dissolved in a mixture of water/acetonitrile (1/2.5v/v) and was added to the isoglutamine solution. The mixture was stirred at 50 °C for three hours before being lyophilized. The obtained crude product was washed with diethyl ether to remove residual DIEA and was dried under vacuum (52% yield).
Same Skeleton Products
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