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[ CAS No. 127512-29-2 ] {[proInfo.proName]}

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Chemical Structure| 127512-29-2
Chemical Structure| 127512-29-2
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Product Details of [ 127512-29-2 ]

CAS No. :127512-29-2 MDL No. :MFCD01321074
Formula : C41H77NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 648.05 Pubchem ID :-
Synonyms :
18:1 DAP;1,2-Dioleoyl-3-dimethylammonium-propane

Calculated chemistry of [ 127512-29-2 ]

Physicochemical Properties

Num. heavy atoms : 46
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.85
Num. rotatable bonds : 37
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 203.72
TPSA : 55.84 Ų

Pharmacokinetics

GI absorption : None
BBB permeant : None
P-gp substrate : None
CYP1A2 inhibitor : None
CYP2C19 inhibitor : None
CYP2C9 inhibitor : None
CYP2D6 inhibitor : None
CYP3A4 inhibitor : None
Log Kp (skin permeation) : None cm/s

Lipophilicity

Log Po/w (iLOGP) : None
Log Po/w (XLOGP3) : None
Log Po/w (WLOGP) : 12.08
Log Po/w (MLOGP) : None
Log Po/w (SILICOS-IT) : None
Consensus Log Po/w : None

Druglikeness

Lipinski : None
Ghose : None
Veber : None
Egan : None
Muegge : None
Bioavailability Score : None

Water Solubility

Log S (ESOL) : None
Solubility : None mg/ml ; None mol/l
Class : None
Log S (Ali) : None
Solubility : None mg/ml ; None mol/l
Class : None
Log S (SILICOS-IT) : None
Solubility : None mg/ml ; None mol/l
Class : None

Medicinal Chemistry

PAINS : None alert
Brenk : None alert
Leadlikeness : None
Synthetic accessibility : None

Safety of [ 127512-29-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 127512-29-2 ]

* 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 [ 127512-29-2 ]

[ 127512-29-2 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 112-80-1 ]
  • [ 623-57-4 ]
  • [ 127512-29-2 ]
YieldReaction ConditionsOperation in experiment
88.9% 2.41 kg of Nu,Nu'-carbonyldiimidazole is dissolved at room temperature in 6.33 kg of dry acetonitrile. The resultant solution is heated to 25°C. Then 4.0 kg of oleic acid is pumped into the solution over a period of 60 minutes while the reaction temperature is regulated below 35°C by the variation of the addition speed (formation of carbon dioxide gas). After the addition is completed the reaction solution is stirred for additional 90 minutes at 30°C (gas evolution ended). Then 11 g of 1 ,8-diazabicyclo[5.4.0]undec-7-ene is added followed by a solution of 0.83 kg of racemic (R,S)-3-(dimethylamino)- 1 ,2-propanediol in 0.37 kg of dry acetonitrile. Stirring at 30°C is continued for 21 hours. The resultant emulsion is cooled to 25°C and stirring is stopped. Two layers appear. The lower layer is isolated, degassed at 1 mbar/25°C for 200 minutes and finally diluted with 11.7 kg n-heptane. To the solution is added 1.21 kg of basic aluminium oxide and the suspension is stirred for 3 hours at 0°C. The suspension is filtered and the filter residue is washed with 1.5 kg of n-heptane previously cooled down to 0°C. The combined filtrates are homogenized to yield 15.9 kg solution of 4.08 kg pure (2R,S)-DODAP in n-heptane (lot no. MBA-116, assay: 25.7percent, yield:88.9percent).
11.12 g With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In chloroform; at 20 - 30℃; for 1h; <strong>[623-57-4]3-(dimethylamino)-1,2-propanediol</strong> 2.00 g (16.78 mmol, manufactured by Tokyo Chemical Industry Co., Ltd.), Oleic acid 9.48 g (33.56 mmol, Nisshin Oil Co., Ltd. "EXTRA OLEIN 99"), 4-dimethylaminopyridine 0.41 g (3.36 mmol, product of Koei Chemical Industry Co., Ltd.) was dissolved in 120 g of chloroform. There, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride 7.72 g (40.27 mmol, product of Tokyo Chemical Industry Co., Ltd.) And the mixture was stirred at 20 to 30 ° C. After 1 hour, it was washed with 120 g of ion exchange water and 120 g of 25 wtpercent saline, and 3.0 g of anhydrous magnesium sulfate was added to the organic layer and stirred. The magnesium sulfate was filtered off, The filtrate was desolvated with an evaporator to obtain DODAP (yield: 11.12 g, 17.16 mmol).
  • 2
  • [ 127512-29-2 ]
  • [ 74-88-4 ]
  • (+/-)-N,N,N-trimethyl-N-[2,3-bis(tetradecanoyloxy)propyl]ammonium iodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% In chloroform; dimethyl sulfoxide at 70℃; for 1h; microwave irradiation; 1A The tertiary amine II (0.15Og, 0.28mmoles) and methyl iodide (0.0468g, 0.33 mmoles) were taken in a 10 mL thick walled pyrex glass with a stirrer bar, dissolved in ImL of chloroform.-dimethylsulfoxide (1:1). The reaction was carried out at 70°C, 150W, 300psi in a microwave synthesizer for 1 hour. The solvents were removed on a rotary evaporator followed by vacuum pump. The residue was loaded on a silica gel EPO (230-400 mesh size) and eluted with 8% methanol in chloroform to give a white solid on subsequent lyophilization (0.148g, yield 96%, Rf~ 0.2)1H-NMR: (400 MHz, CDCl3 ) (ESI) m/z (M) + 554.48; HRMS (ESI) m/z: Calcd (for C34H68NO4, the 4° ammonium ion, 100%) 554.5148, found 554.5140.The synthesis of a second crop of 1 yielded the following characteristics: 1H-
  • 3
  • [ 112-77-6 ]
  • [ 623-57-4 ]
  • [ 127512-29-2 ]
YieldReaction ConditionsOperation in experiment
95% With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at -5 - 20℃;Inert atmosphere; Large scale; 3-dimethylamino-1,2-propanediol 500 g,1600 g of diisopropylethylamine and 15 L of tetrahydrofuran are added to the reaction vessel.Cool down to minus 5°CThe gas in the replacement axe is nitrogen,A solution of 2800 g of oleic acid chloride in tetrahydrofuran was slowly added dropwise.Keep the temperature in the reactor not higher than 10°C,Then slowly warm up to room temperature,Continue to react for 2-3 hours,Concentrate under reduced pressure,Add Ethyl Acetate and Cold Water,Liquid separation,The organic phase is washed with saturated saline solution.Liquid separation,The organic phase is dried over anhydrous magnesium sulfate,filter.The organic phase is concentrated and dried under reduced pressure to obtain1,2-Dioleoyl-3-diamino-propane2580 g, yield 95percent.
72% With pyridine;dmap; In dichloromethane; at 0 - 20℃; for 6h; An alternative synthesis is as follows: to a solution of 3-(dimethylamino)-l,2- propandiol (0.2 mL, 1.68 mmol), pyridine (0.55 mL, 6.72 mmol) and DMAP (20 mg, 0.17 mmol), in CH2CI2 (10 mL) at 00C was added dropwise oleoyl chloride (1.38 mL, 4.2 mmol). The reaction mixture was allowed to warm up slowly to room temperature. After stirring for 6 hours at room temperature, the reaction mixture was diluted with CH2Cl2 (50 mL), washed sequentially with 5percent aqueous sodium bicarbonate (15 mL), water (15 mL), and saturated aqueous NaCl (15 mL). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, elution with 0.2percent MeOH in CHCl3) furnished compound II (0.782 g, 72percent) as oily liquid. NMR spectra coordinates are as follows: 1H NMR (CDCl3): delta 5.47-5.32 (m, 4H), 5.28-5.18 (m, IH), 4.40 (dd, J= 11.8, 3.0 Hz, IH)5 4.13 (dd, J= 12.0, 6.8 Hz, IH)5 2.56-2.42 (m, 2H)5 2.35 (dt, J= 7.6, 2.8 Hz, 4H), 2.30 (s, 6H), 2.12-1.97 (m, 8H), 1.71- 1.58 (m, 4H), 1.44-1.23 (m, 40H), 0.92 (t, J= 7.0 Hz, 6H).Another crop of of (+/-)-N,N-Dimethyl-N-[2,3-bis(9-(2)-octadecanoyloxy)- propyl] amine (II) was prepared and had the following 1H NMR characteristics: (400
With pyridine; In chloroform; at 4℃;Product distribution / selectivity; In the herein reproduced experiment of Feigner et al., all experimental conditions have been chosen to stay in close accordance with US5,264,618 (Feigner et al.), Example 5, column 27, lines 15 to 47. 31.5 g of oleoylchloride (FLUKA 0733IAH) dissolved in 125 ml chloroform was added dropwise at 4°C under cooling over a period of 11/2 hour to 5.0 g of 3-(dimethylamino)-1 ,2-propanediol, dissolved in 37.5 ml chloroform and 25 ml of pyridine. The yellow solution was stirred overnight. Then 125 ml of cold water and 125 ml diethylether was added. The organic phase was washed twice with 100 ml of 0.5N HCL and also twice with 100 ml 0.5N sodium bicarbonate solution. 39 g anhydrous sodium sulfate was added and the so obtained suspension was filtrated and washed with 100 ml chloroform. The filtrate was then concentrated under reduced pressure at 40°C. 40.1 g of a brown liquid (SM-0318-A) having a (2R,S)-DODAP content of 24.3percent w/w measured by HPLC resulted. A further drying under reduced pressure at 60°C resulted in a reduction of weight to 31.2 g.31.0 g of this material was purified by silicic acid column chromatography as follows:Silica gel: 129 g (the amount of silica gel was calculated relative to the amount (2R,S)-DODAP) Merck 60 F 63-200umColumn: diameter 4 cm, height 60 cmFlow: about 8 ml/minAs mobile phase first 1 ,500 ml methylene chloride (fractions 1-27), then 1 ,000 ml methylene chloride/methanol 95:5 (fractions 28-47) and finally 1 ,000 ml methanol was used. Fractions were collected and combined according to their TLC analysis. So fractions 4-33 were concentrated together under reduced pressure. 10.8 g of a brown oil (SM-0318-B) having a (2R,S)-DODAP content of 65.6percent w/w measured by HPLC resulted. And fractions 34-42 resulted in 12.6 g of a brown oil (SM 0318-D) having a (2R,S)-DODAP content of 54.2percent w/w measured by HPLC.10.4 g Methylene chloride was added to 9.6 g of the compound obtained out of the fractions 4-33 (SM-0318-B) in a high pressure glass tube. The glass tube was then closed and the brownish solution was heated over night at 50°C to form an emulsion. Then the tube was opened and residual methylene chloride was removed by evaporation. 8.0 g of a yellow wax (SM-0318-E) having a (2R,S)-DOTAP chloride content of 65.0percent w/w and 1.3percent w/w (2R,S)-DODAP both measured by HPLC resulted.14.0 g acetonitrile was added to this wax (SM-0318-E). The so obtained emulsion was transferred with 80 ml acetonitrile (to obtain a ratio solid to solvent of about 1 :12) into a flask and cooled down to 20°C. Nocrystallisation could be observed. At 20°C a solidified honey like yellow- brownish material resulted which even when only slightly warming it up tended to become a sticky viscous brownish material.ConclusionThe data demonstrate that 1 ,2-dioleoyl-3-propyltrimethylammonium chloride ((2R,S)-DOTAP chloride) prepared according to the above procedure, which is in accordance with US 5,264,618 (Feigner et al), Example 5, column 27, lines 15 to 47 cannot be obtained in a crystalline form.See also Figures 6 and 7 illustrating (2R,S)-DOTAP chloride emulsion (SM- 0318-E) in acetonitrile when cooling down and (2R,S)-DOTAP chloride emulsion (S -0318-E) in acetonitrile after having been cooled it down to - 20°C, respectively.
  • 4
  • [ 127512-29-2 ]
  • [ 74-88-4 ]
  • (+/-)-N,N,N-trimethyl-N-[2,3-bis(9(Z)-octadecanoyloxy)propyl]ammonium iodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% In chloroform; dimethyl sulfoxide at 70℃; for 1h; Microwave irradiation;
3.7 g In acetone at 20 - 30℃; for 3h; 5 Production of N-[1-(2,3-dioleoyloxy)propyl]-N,N,N-trimethylammonium iodide 3.00 g (4.84 mmol) of DODMA was dissolved in 30 g of acetone, 1.03 g (7.26 mmol) of methyl iodide was added thereto, and the mixture was stirred at 20 to 30 ° C. After 3 hours, the reaction solution was desolvated with an evaporator to obtain DOTMA-I (yield: 3.70 g, 4.86 mmol).
  • 5
  • [ 1120-71-4 ]
  • [ 127512-29-2 ]
  • [ 1352945-51-7 ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine In methanol; dichloromethane at 40℃; for 18h;
  • 6
  • [ 5292-43-3 ]
  • [ 127512-29-2 ]
  • [ 1378942-82-5 ]
YieldReaction ConditionsOperation in experiment
45% With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 40℃; for 48h;
  • 7
  • [ 127512-29-2 ]
  • [ 1378942-53-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 48 h / 40 °C 2: trifluoroacetic acid / TIPS; dichloromethane / 1 h / 20 °C
  • 8
  • [ 75-09-2 ]
  • [ 127512-29-2 ]
  • N-[2,3-dioleoyloxypropyl]-N,N,N-trimethylammonium chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 50℃; Sealed tube; 1 In the herein reproduced experiment of Feigner et al., all experimental conditions have been chosen to stay in close accordance with US5,264,618 (Feigner et al.), Example 5, column 27, lines 15 to 47. 31.5 g of oleoylchloride (FLUKA 0733IAH) dissolved in 125 ml chloroform was added dropwise at 4°C under cooling over a period of 1½ hour to 5.0 g of 3-(dimethylamino)-1 ,2-propanediol, dissolved in 37.5 ml chloroform and 25 ml of pyridine. The yellow solution was stirred overnight. Then 125 ml of cold water and 125 ml diethylether was added. The organic phase was washed twice with 100 ml of 0.5N HCL and also twice with 100 ml 0.5N sodium bicarbonate solution. 39 g anhydrous sodium sulfate was added and the so obtained suspension was filtrated and washed with 100 ml chloroform. The filtrate was then concentrated under reduced pressure at 40°C. 40.1 g of a brown liquid (SM-0318-A) having a (2R,S)-DODAP content of 24.3% w/w measured by HPLC resulted. A further drying under reduced pressure at 60°C resulted in a reduction of weight to 31.2 g.31.0 g of this material was purified by silicic acid column chromatography as follows:Silica gel: 129 g (the amount of silica gel was calculated relative to the amount (2R,S)-DODAP) Merck 60 F 63-200umColumn: diameter 4 cm, height 60 cmFlow: about 8 ml/minAs mobile phase first 1 ,500 ml methylene chloride (fractions 1-27), then 1 ,000 ml methylene chloride/methanol 95:5 (fractions 28-47) and finally 1 ,000 ml methanol was used. Fractions were collected and combined according to their TLC analysis. So fractions 4-33 were concentrated together under reduced pressure. 10.8 g of a brown oil (SM-0318-B) having a (2R,S)-DODAP content of 65.6% w/w measured by HPLC resulted. And fractions 34-42 resulted in 12.6 g of a brown oil (SM 0318-D) having a (2R,S)-DODAP content of 54.2% w/w measured by HPLC.10.4 g Methylene chloride was added to 9.6 g of the compound obtained out of the fractions 4-33 (SM-0318-B) in a high pressure glass tube. The glass tube was then closed and the brownish solution was heated over night at 50°C to form an emulsion. Then the tube was opened and residual methylene chloride was removed by evaporation. 8.0 g of a yellow wax (SM-0318-E) having a (2R,S)-DOTAP chloride content of 65.0% w/w and 1.3% w/w (2R,S)-DODAP both measured by HPLC resulted.14.0 g acetonitrile was added to this wax (SM-0318-E). The so obtained emulsion was transferred with 80 ml acetonitrile (to obtain a ratio solid to solvent of about 1 :12) into a flask and cooled down to 20°C. Nocrystallisation could be observed. At 20°C a solidified honey like yellow- brownish material resulted which even when only slightly warming it up tended to become a sticky viscous brownish material.ConclusionThe data demonstrate that 1 ,2-dioleoyl-3-propyltrimethylammonium chloride ((2R,S)-DOTAP chloride) prepared according to the above procedure, which is in accordance with US 5,264,618 (Feigner et al), Example 5, column 27, lines 15 to 47 cannot be obtained in a crystalline form.See also Figures 6 and 7 illustrating (2R,S)-DOTAP chloride emulsion (SM- 0318-E) in acetonitrile when cooling down and (2R,S)-DOTAP chloride emulsion (S -0318-E) in acetonitrile after having been cooled it down to - 20°C, respectively.
  • 9
  • [ 74-87-3 ]
  • [ 127512-29-2 ]
  • N-[2,3-dioleoyloxypropyl]-N,N,N-trimethylammonium chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% In dichloromethane at 85℃; 2 Example 2 Preparation of (2,3-Dioleoyl-propyl) Trimethylammonium Chloride With reference to Table 1, the reaction temperature, pressure, and influence of the solvent on the product are examined. The 1,2-dioleoyl-3-diamino-propane and the reaction solvent were added to the autoclave to replace the gas in the axe with nitrogen, then the nitrogen was replaced with methyl chloride, and the pressure was gradually raised to 1.5 MPa to maintain the pressure. , slowly warm up to the set temperature, and react at this temperature and pressure for 5-24 hours, to room temperature, vent pressure, the reaction solution is transferred to the atmospheric pressure reactor, slowly add the crystallization solvent, at this time there is white The solid precipitated, continue to stir at room temperature for 2-5 hours, and was filtered. The solid was washed with a crystalline solvent and the solid was dried under reduced pressure to give (2,3-dioleoyl-propyl)trimethylammonium chloride. The raw material conversion rate was calculated.
With sodium iodide In isopropyl alcohol at 30℃; for 137h; Industry scale; Inert atmosphere; 1 23.4 kg solution of 3.52 kg pure (2R,S)-DODAP in n-heptane (15.9 kg of lot no. MBA-116 and 7.5 kg of lot no. MBA-117) is charged into the reaction vessel and the n-heptane is distilled off at a jacket temperature of 60°C and reduced pressure. When the vacuum remains stable at 8 mbar the jacket temperature is adjusted to 25°C. Then 7.0 kg of 2-propanol is added followed by 3.1 g of sodium iodide. Then the reaction temperature is adjusted to 30°C and the nitrogen atmosphere is replaced by a methyl chloride atmosphere with constant absolute pressure of 1200 mbar. The reaction mixture is stirred under these conditions for 137 hours until the methylation reaction of (2R,S)-DODAP to (2R,S)-DOTAP Chloride is finished (96% conversion). The consumption of methyl chloride is 1.39 kg.
  • 10
  • 1-bromo-3-propanesulfate - diisopropylethylamine salt [ No CAS ]
  • [ 127512-29-2 ]
  • [ 1619934-61-0 ]
YieldReaction ConditionsOperation in experiment
45% In N,N-dimethyl-formamide at 60℃; for 18h; Inert atmosphere;
  • 11
  • [ 10108-25-5 ]
  • [ 127512-29-2 ]
  • (9Z)-N,N-dimethyl-N-(3-(oleoyloxy)-2-((9Z)-2-oxooctadecenyloxy)propyl)-13-oxo-3,6,9,12-tetraoxatriacont-21-en-1-aminium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
11% In acetone at 80℃; for 48h; Sealed tube; Tertiary Amine (18) TriChain ionic compound (9Z)-N^V-dimethyl-N-(3-(oleoyloxy)-2-((9Z)-2- oxooctadecenyloxy) propyl)-13-oxo-3,6,9,12-tetraoxatriacont-21-en-l-aminium bromide (TC-DOesDEG4) (19) was synthesised by the quaternisation of (2,3-bis- heptadec-9-enylcarboxypropyl)-dimethylamine (18) with the 4-EG oleoyl ester (20). A solution of the amine 18 (0.610 g, 0.941 mmol) and the 4-EG oleoyl ester 20 (0.640 g, 1.22 mmol) in acetone (2 mL) were stirred in a sealed tube at 80 °C for 48 h. The acetone was removed in vacuo. Purification by flash silica chromatography (0239) (CH2Cl2/MeOH, 19: 1) yielded 19 as a pale yellow oil (118 mg, 11%). RF 0.24 (0240) (CH2Cl2/MeOH, 19: 1); vmax (neatycm"1 2924, 2854, 1740, 1465; NMR (500 MHz; CDCb) δ 0.86 (t, J= 6.8 Hz, 9H), 1.25-1.32 (m, 60H), 1.58 (m, 6H), 1.99 (m, 12H), 2.30 (t, J= 7.5 Hz, 4H), 2.34 (m, 2H), 3.44 (s, 3H), 3.51 (s, 3H), 3.64-3.68 (m, 11H), 3.82 (dd, J= 13.5 and 10.0 Hz, 1H), 3.94 (m, 2H), 4.05 (m, 2H), 4.13 (m, 1H), 4.20 (t, J= 5.0 Hz, 2H), 4.35 (d, J = 13.5 Hz, 1H), 4.48 (dd, J= 12.3 and 3.3 Hz, 1H), 5.28- 5.35 (m, 6H), 5.64 (m, 1H); 13C MR (125 MHz; CDCb) δ 14.2, 22.7, 24.7, 24.8, 25.0, 25.7, 27.2, 27.3, 29.1-29.8, 31.6, 32.0, 34.0, 34.3, 52.8, 52.9, 63.2, 63.3, 64.0, 64.9, 65.6, 65.8, 69.3, 70.1, 70.45, 70.48, 70.6, 129.7-130.1 (signals superimposed), 172.9, 173.2, 173.8; m/z [HRMS ES+] found [M-Br]+ 1088.9382. C67Hi26N09 requires 1088.9433; m/z (+ES) 1089 ([M-Br]+, 100%).
  • 12
  • 2-(2-(2-(bromoethoxy)ethoxy)ethoxy)ethyl acetate [ No CAS ]
  • [ 127512-29-2 ]
  • N-(2,3-bis(oleoyloxy)propyl)-N,N-dimethyl-13-oxo-3,6,9,12-tetraoxatetradecan-1-aminium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% In acetone at 90℃; for 48h; Sealed tube;
  • 13
  • 2-(2-(2-(2-bromoethoxy)ethoxy)ethoxy)ethyl dodecanoate [ No CAS ]
  • [ 127512-29-2 ]
  • N-(2,3-bis(oleoyloxy)propyl)-N,N-dimethyl-13-oxo-3,6,9,12-tetraoxatetracosan-1-aminium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% In acetone at 90℃; for 48h; Sealed tube;
  • 14
  • [ 72593-77-2 ]
  • [ 127512-29-2 ]
  • N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-N,N-dimethyl-2,3-bis(oleoyloxy)propan-1-aminium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% In acetone at 90℃; for 48h; Sealed tube;
  • 15
  • [ 85141-94-2 ]
  • [ 127512-29-2 ]
  • N-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)-N,N-dimethyl-2,3-bis(oleoyloxy)propan-1-aminium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% In tetrahydrofuran at 90℃; for 48h; Sealed tube;
  • 16
  • 2-(2-(2-hydroxyethoxy)ethoxy)ethyl 5-bromopentanoate [ No CAS ]
  • [ 127512-29-2 ]
  • N-(2,3-bis(oleoyloxy)propyl)-5-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)-N,N-dimethyl-5-oxopentan-1-aminium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In acetone at 80℃; for 48h; Sealed tube;
  • 17
  • 2-(2-(2-methoxyethoxy)ethoxy)ethyl 5-bromopentanoate [ No CAS ]
  • [ 127512-29-2 ]
  • N-(2,3-bis(oleoyloxy)propyl)-N,N-dimethyl-12-oxo-2,5,8,11-tetraoxahexadecan-16-aminium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% In acetone at 90℃; for 48h; Sealed tube;
  • 18
  • (9Z)-2-(2-(2-(2-bromoethoxy)ethoxy)ethoxy)ethyl oleate [ No CAS ]
  • [ 127512-29-2 ]
  • N,N-dimethyl-N-(3-(oleoyloxy)-2-((9Z)-2-oxooctadecenyloxy)propyl)-13-oxo-3,6,9,12-tetraoxatriacont-(21Z)-en-1-aminium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
11% In acetone at 80℃; for 48h; Sealed tube;
  • 19
  • (9Z)-2-(2-(2-(5-bromopentanoyloxy)ethoxy)ethoxy)ethyl oleate [ No CAS ]
  • [ 127512-29-2 ]
  • N,N-dimethyl-N-(3-((9Z)-octadecenyloxy)-2-(oleoyloxy)-3-oxopropyl)-5,16-dioxo-6,9,12,15-tetraoxatritriacont-(24Z)-en-1-aminium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% In tetrahydrofuran at 80℃; for 48h; Sealed tube;
YieldReaction ConditionsOperation in experiment
97.5% With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 24h; 2 Examples 1 to 3 General procedure: 56g of hexadecanoic acid (0.22mol),12g of N, N-dimethylamino-1,2-propanediol (0.1mol) was added to a 500mL reaction flask,Add 300mL of dichloromethane,After sufficient stirring, 27.8 g of N, N'-diisopropylcarbodiimide (DIC) (0.22 mol) and 0.2 g of 4-dimethylaminopyridine (DMAP) were added,After the reaction was stirred at room temperature for 24h,Filtration, the solid obtained after rotary distillation of the filtrate was further recrystallized and purified,54 g of product was obtained with a yield of 96.8%.
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