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[ CAS No. 104162-47-2 ] {[proInfo.proName]}

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Chemical Structure| 104162-47-2
Chemical Structure| 104162-47-2
Structure of 104162-47-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 104162-47-2 ]

CAS No. :104162-47-2 MDL No. :MFCD22200991
Formula : C41H81NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :GLGLUQVVDHRLQK-WRBBJXAJSA-N
M.W : 620.09 Pubchem ID :11181107
Synonyms :

Calculated chemistry of [ 104162-47-2 ]

Physicochemical Properties

Num. heavy atoms : 44
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.9
Num. rotatable bonds : 37
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 203.32
TPSA : 21.7 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) : 13.02
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 [ 104162-47-2 ]

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

Application In Synthesis of [ 104162-47-2 ]

* 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 [ 104162-47-2 ]

[ 104162-47-2 ] Synthesis Path-Downstream   1~27

  • 1
  • [ 13044-38-7 ]
  • [ 623-57-4 ]
  • [ 104162-47-2 ]
  • 2
  • [ 104162-47-2 ]
  • [ 574-98-1 ]
  • {2,3-Bis-[((Z)-octadec-9-enyl)oxy]-propyl}-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-dimethyl-ammonium; bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% at 110℃; for 18h;
  • 3
  • [ 623-57-4 ]
  • oleyl toluenesulfonate [ No CAS ]
  • [ 104162-47-2 ]
  • 4
  • [ 104162-47-2 ]
  • [ 714192-23-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 77 percent / 18 h / 110 °C 2: 80 percent / hydrazine / methanol / 18 h / Heating
  • 5
  • [ 104162-47-2 ]
  • 2,3-dioleoyloxy-N-[2-(spermine-carboxamido)ethyl]-N,N-dimethyl-1-propanaminum chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 77 percent / 18 h / 110 °C 2: 80 percent / hydrazine / methanol / 18 h / Heating 3: 70 percent / PyBop; HOBt; DIPEA / CH2Cl2 / 12 h 4: 65 percent / HCl / dioxane / 3 h
  • 6
  • [ 104162-47-2 ]
  • ({2,5-bis-[<i>tert</i>-butoxycarbonyl-(3-<i>tert</i>-butoxycarbonylamino-propyl)-amino]-pentanoylamino}-methyl)-(2,3-bis-octadec-9-enyloxy-propyl)-dimethyl-ammonium [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 77 percent / 18 h / 110 °C 2: 80 percent / hydrazine / methanol / 18 h / Heating 3: 70 percent / PyBop; HOBt; DIPEA / CH2Cl2 / 12 h
  • 7
  • [ 104162-47-2 ]
  • [ 574-98-1 ]
  • 2H-Isoindole-2-ethanaminium, N-[2,3-bis(9-octadecenyloxy)-propyl]-1,3-dihydro-N,N-dimethyl-1,3-dioxo-, bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% In methanol; chloroform 2 Example 2 Example 2 2H-Isoindole-2-ethanaminium, N-[2,3-bis(9-octadecenyloxy)-propyl]-1,3-dihydro-N,N-dimethyl-1,3-dioxo-, bromide (7). 2,3-dioleyloxy-1-(N,N-dimethylamino)propane (1.238 g, 2 mmole) was combined with N-(2-bromoethyl)phthalimide and heated under argon (130° C.) for 18 hours. TLC analysis (Silica gel 20% MeOH/CHCl3) showed the lipid starting material was completely consumed. The desired material was purified by flash chromatography using step gradient of hexane/CHCl3 (1:1), to 20% MeOH/CHCl3. The desired material was obtained in 25% yield as a gum. IR: 2920, 2850, 1760(s), 1720, 1460, 1390 cm-1.
  • 8
  • [ 623-57-4 ]
  • [ 35709-09-2 ]
  • [ 104162-47-2 ]
YieldReaction ConditionsOperation in experiment
76% With potassium hydroxide; In 5,5-dimethyl-1,3-cyclohexadiene; ethyl acetate; Example 1 2,3 -dioleyloxy-1-(N,N-dimethylamino)propane (1). To a three-necked, 2-liter round bottom flask equipped with a Dean-Stork trap were added 3 -dimethylamino-1,2 -propanediol (6.08 g, 51.1 mmoles), xylene (1300 ml) and KOH (8.0 g). The solution was refluxed for 2 hours while removing water azeotropically via the Dean-Stork trap. Oleyl mesylate (40.0 g, 115.6 mmoles) in 100 ml xylene was added to the reaction mixture drop-wise in 30 minutes. Refluxing was continued for 3 hours and the reaction mixture concentrated to a gum. The gum was triturated with 400 ml hexane and filtered. The solid was washed with 100 ml hexane followed with 200 ml ethyl acetate. The filtrates were combined, concentrated and subjected to f lash chromatography. 2,3-dioleyloxy-1- (N, N-dimethylamino) propane was obtained as a colorless oil in 76percent yield, TLC: Rf =0.37 (Silica gel: 5percent EtOAc: hexane); IR: 2925, 2850, 1469, 1120, 1040 cm-1; H-NMR (CDCl3) delta 5.35 (t, 4H), 4.13 (q, 1H) 3.4-3.65 (m, 6H), 2.35-2.45 (m, 2H), 2.25 (S, 6H), 1.95-2.05 (m, 8H), 1.5-1.65 (m, 4H), 1.2-1.45 (m, 4H) 0.9 (t, 6H).
95 g [0217] 1,2-Dioleyloxy-3-dimethylaminopropane (DODMA) DLinDMA was synthesized in the same manner, exceptthat oleyl mesylate was replaced with linoley mesylate.[0218] Benzene (800 mL) was added to sodium hydride (52g, 95percent, 2.06 mol) in a 3L pear-shaped round bottom flaskwith a stir bar under argon. A solution of N,N-dimethylaminopropane-1,2-diol (28.1g, 234.8 mmol) in benzene (200mL)was slowly added to the reaction flask under argon, rinsing with a further 50mL of benzene and allowed to stir for 10minutes. [0219] Oleyl mesylate (200.3g, 578.9 mmol) in benzene (200mL) was added to the reaction mixture under argon andrinsed with a further 1200mL of benzene. The reaction mixture was allowed to reflux under argon overnight. [0220] The reaction mixture was transferred to 4L erlenmeyer flask and ethanol (100 mL) was added slowly underargon to quench unreacted sodium hydride. Additional ethanol (1300 mL) was added to give a total ethanol content of1400mL such that benzene:ethanol is 1:1. The reaction mixture (800mL) was aliquoted to a 2L separatory funnel and240mL water was added (benzene:ethanol:water 1:1:0.6 v/v). The organic phase was collected and the aqueous layerwas re-extracted with benzene (100mL).[0221] Oleyl mesylate (200.3g, 578.9 mmol) in benzene (200mL) was added to the reaction mixture under argon andrinsed with a further 1200mL of benzene. The reaction mixture was allowed to reflux under argon overnight. This stepwas repeated again. [0222] The combined organic fractions were dried with anhydrous magnesium sulphate (30g) and filtered under vacuumusing a sintered glass funnel. Solvent was removed on a rotovap (water bath 50 - 60hC). The viscous oily product wasredissolved in dichloromethane (300 mL) and vacuum filtered through a sintered glass funnel with a filter paper andsilica gel 60 (80g, 230 - 400 mesh). Dichloromethane was removed on a rotovap at 50 - 60hC. [0223] The product was purified by column chromatography. A total of 151 g product was divided into two ?75g aliquotsand loaded onto two 600g silica gel 60 columns. The product was dissolved in 2percent MeOH in dichloromethane (?1:1 w/v)prior to loading onto the column. 2percent MeOH in dichloromethane (?1 L) was used until product came out. Approximately1 L of 5percent, 7.5percent and then 10percent MeOH in dichloromethane were used to elute the columns collecting ?200 mL fractions.[0224] Fractions with a top or bottom spot on TLC (impurity) and product were rotovaped separately from the purefractions. Impure DODMA was collected from other batches, added together, and put down a column a second time topurify. The yield of DODMA was 95g.
YieldReaction ConditionsOperation in experiment
65% Stage #1: With sodium hydride In mineral oil; benzene for 0.5h; Inert atmosphere; Stage #2: In mineral oil; benzene for 18h; Inert atmosphere; Reflux; 1 Synthesis of DSDMA and DODMA General procedure: Synthesis of DSDMA and DODMA: (0248) DSDMA and DODMA were synthesized using the respective alkyl bromides with methodology derived from that of a DOTMA precursor (Feigner et al, PNAS USA, 84, 7413-7417 (1987)). 3-(Dimethylamino)-1,2-propanediol (714 mg, 6 mmol) and 95% sodium hydride (NaH, 1.26 g, 50 mmol) were stirred in benzene (30 mL) under argon for 30 minutes. The correct (either oleyl or stearyl) alkyl bromide (5.0 g, 15 mmol) was added and the reaction refluxed under argon for 18 hours. The reaction mixture was then cooled in an ice bath while quenching via the slow addition of ethanol. Following dilution with a further 150 mL of benzene, the mixture was washed with distilled water (2×150 mL) and brine (150 mL), using ethanol (20 mL) to aid phase separation if necessary. The organic phase was dried over magnesium sulphate and evaporated. The crude product was purified on a silica gel (Kiesel Gel 60) column eluted with chloroform containing 0-5% methanol. Column fractions were analyzed by thin layer chromatography (TLC) (silica gel, chloroform/methanol 9:1 v/v, visualized with molybdate) and fractions containing pure product (Rf=0.5) were pooled and concentrated. The product was decolorized by stirring for 30 minutes in a suspension of activated charcoal (1 g) in ethanol (75 mL) at 60° C. The charcoal was removed by filtration through Celite, and the ethanol solution concentrated to typically yield 2.4 g (65%) of pure product. 1H-NMR (DSDMA): δH 3.65-3.32 (m, 7H, OCH, 3×OCH2), 2.45-2.31 (m, 2H, NCH2), 2.27 (s, 6H, 2×NCH3), 1.61-1.45 (m, 4H, OCH2CH2), 1.40-1.17 (m, 60H, Hstearyl), 0.86 (t, 6H, CH2CH3). 1H-NMR (DODMA): δH 5.4-5.27 (m, 4H, 2×CH═CH), 3.65-3.35 (m, 7H, OCH, 3×OCH2), 2.47-2.33 (m, 2H, NCH2), 2.28 (s, 6H, 2×NCH3), 2.06-1.94 (m, 8H, 4×CH2CH═CH), 1.61-1.50 (m, 4H, OCH2CH2), 1.38-1.20 (m, 48H, Holeyl), 0.88 (t, 6H, CH2CH3).
1 Preparation of DOTMA {-[1-(2,3,-dioleyloxy)propyl]-N,N,Ntrimethylammonium chloride} Preparation of DOTMA {-[1-(2,3,-dioleyloxy)propyl]-N,N,Ntrimethylammonium chloride} DOTMA may be prepared according to the following protocol: A mixture of 3-(dimethylamino)-l,2-propanediol (Aldrich; 1.19 g, 10 mmol), potassium tert-butoxide (3.36 g, 30 mmol), and oleyl ptoluenesulfonate (12.7 g, 30 mmol) in xylene (50 ml) was stirred at room temperature and reduced pressure (30 torr; 1 torr=133 Pa) for 30 min and then was heated to 50° C. with stirring for an additional 15 min. The reaction vessel was purged with nitrogen, and the mixture was heated to reflux (~140° C.) for 3 hr. After cooling, the reaction mixture was diluted with hexane (100 ml), and the resulting solution was extracted with water (twice, 50 ml each). The organic layer was concentrated, and the residue was chromatographed over silica gel by elution with a mixture of hexane and diethyl ether (1:2) to afford the intermediate 2,3-dioleyloxyl(dimethylamino)propane as a colorless oil.
  • 10
  • [ 623-57-4 ]
  • [ 6110-54-9 ]
  • [ 104162-47-2 ]
YieldReaction ConditionsOperation in experiment
With potassium tert-butylate; (B) DOTMA Synthesis and Liposome Preparation STR7 DOTMA (N-(1-(2,3,-Diolelyloxy)propyl)-N,N,N-trimethylammonium chloride) was prepared as outlined in FIG. 1. A mixture of <strong>[623-57-4]3-(dimethylamino)-1,2-propanediol</strong> (Aldrich Chemical Co., 1.19 g, 10 mmol), potassium tert-butoxide (3.36 g, 30 mmol) and oleyl p-toluenesulfonate (12.7 g, 30 mmol) in xylenes (50 ml) was stirred at room temperature and reduced pressure (30 Torr) for 30 min, and was then heated to 50° C. with stirring for an additional 15 min. The reaction vessel was purged with nitrogen, and the mixture was heated to reflux (approximately 140° C.) for 3 hrs. After cooling, the reaction mixture was diluted with hexane (100ml), and the resulting solution was extracted with water (2*50 ml). The organic layer was concentrated, and the residue was chromatographed over silica gel by elution with a mixture of hexanes and ether (1:2) to afford the intermediate 2,3-dioleyloxy-1-(dimethylamino)-propane as a colorless oil.
  • 11
  • [ 104162-47-2 ]
  • [ 5414-19-7 ]
  • [ 625080-83-3 ]
YieldReaction ConditionsOperation in experiment
48% In methanol at 90℃; for 24h; sealed tube;
  • 12
  • [ 104162-47-2 ]
  • [ 629-03-8 ]
  • [ 1050547-78-8 ]
YieldReaction ConditionsOperation in experiment
87% In methanol at 90℃; for 24h; sealed tube;
  • 13
  • [ 104162-47-2 ]
  • [ 57641-67-5 ]
  • [ 625080-79-7 ]
  • 14
  • [ 104162-47-2 ]
  • [ 57641-66-4 ]
  • [ 1050547-56-2 ]
  • 15
  • [ 104162-47-2 ]
  • [ 31255-10-4 ]
  • [ 1173166-34-1 ]
YieldReaction ConditionsOperation in experiment
33% In methanol at 90℃; for 18h; sealed tube;
  • 16
  • [ 104162-47-2 ]
  • [ 31255-26-2 ]
  • [ 1173166-43-2 ]
YieldReaction ConditionsOperation in experiment
22% In acetone at 90℃; for 24h; sealed tube;
  • 17
  • [ 104162-47-2 ]
  • [ 85141-94-2 ]
  • [ 868594-33-6 ]
YieldReaction ConditionsOperation in experiment
58% In methanol at 90℃; for 24h; sealed tube;
  • 18
  • [ 104162-47-2 ]
  • [ 136399-05-8 ]
  • [ 868594-34-7 ]
YieldReaction ConditionsOperation in experiment
34% In methanol at 90℃; for 24h; sealed tube;
  • 19
  • [ 104162-47-2 ]
  • [ 4101-68-2 ]
  • [ 1050547-80-2 ]
YieldReaction ConditionsOperation in experiment
46% In methanol at 90℃; for 24h; sealed tube;
  • 21
  • [ 104162-47-2 ]
  • [ 75-11-6 ]
  • [ 1347051-93-7 ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: 2,3-dioleyloxy-1-(N,N-dimethylamino)propane With dimethyl zinc(II) In hexane; dichloromethane at 0℃; for 1h; Inert atmosphere; Stage #2: diiodomethane In hexane; dichloromethane at 0 - 20℃; for 16h; 1 A solution of DODMA (310 mg, 0.5 mmol) in anhydrous dichloromethane (10 mL) under nitrogen was cooled to 0°C and a 1M solution of diethylzinc in hexanes (5 mL, 5 mmol, 5 eqv) added. The solution was stirred for 1 hour at 0°C then diiodomethane (1.34 g, 404 μ, 5 mmol) was added and the solution was stirred for 16 hours at room temperature under nitrogen. TLC (8% MeOH in CHC13) showed that the starting material was consumed and a very slightly more polar product had formed. The reaction mixture was concentrated and purified by column chromatography. A polar (lower running) impurity coeluted with the product. After concentrating appropriate column fractions they were dissolved in EtOAc and washed with 5% HC1 (2 x 10 mL), water (10 mL), sat. NaHC03 (10 mL), water (10 mL) and brine (10 mL). The solution was dried over MgS04 and concentrated to afford a clear pale yellow oil (200 mg, 62%). 1H NMR analysis showed complete conversion of the c/s-alkenes to cyclopropyl groups.
62% Stage #1: 2,3-dioleyloxy-1-(N,N-dimethylamino)propane With diethylzinc In hexane; dichloromethane at 0℃; for 1h; Inert atmosphere; Stage #2: diiodomethane In hexane; dichloromethane at 20℃; for 16h; Inert atmosphere; 34 Example 34 Synthesis of CP-DODMA Example 34 Synthesis of CP-DODMA CP-DODMA (Compound 57) having the structure shown below was synthesized as described below. A solution of DODMA (310 mg, 0.5 mmol) in anhydrous dichloromethane (10 mL) under nitrogen was cooled to 0° C. and a 1M solution of diethylzinc in hexanes (5 mL, 5 mmol, 5 eqv) added. The solution was stirred for 1 hour at 0° C. then diiodomethane (1.34 g, 404 μL, 5 mmol) was added and the solution was stirred for 16 hours at room temperature under nitrogen. TLC (8% MeOH in CHCl3) showed that the starting material was consumed and a very slightly more polar product had formed. The reaction mixture was concentrated and purified by column chromatography. A polar (lower running) impurity coeluted with the product. After concentrating appropriate column fractions they were dissolved in EtOAc and washed with 5% HCl (2*10 mL), water (10 mL), sat. NaHCO3 (10 mL), water (10 mL) and brine (10 mL). The solution was dried over MgSO4 and concentrated to afford a clear pale yellow oil (200 mg, 62%).
  • 22
  • [ 104162-47-2 ]
  • [ 10108-25-5 ]
  • (9Z)-N-(2,3-bis((9Z)-octadecenyloxy)propyl)-N,N-dimethyl-13-oxo-3,6,9,12-tetraoxatriacont-21-en-1-aminium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% In acetone at 90℃; for 48h; Sealed tube; TC-DODEG4 (14) TriChain ionic compound (9Z)-N-(2,3-bis((9Z)-octadecenyloxy)propyl)-N /V- dimethyl-13-oxo-3,6,9,12-tetraoxatriacont-21-en-l-aminium bromide (TC- DODEG4) (14) was synthesised by the quaternisation of (2,3-bis-octadec-9- en loxypropyl)-dimethylamine (16) with the 4-EG oleoyl ester (20). (0234) A solution of the amine (16) (0.260 g, 0.420 mmol) and the 4-EG oleoyl ester (20) (0.240 g, 0.460 mmol) in acetone (2 mL) were stirred in a sealed tube at 90 °C for 48 h. The acetone was removed in vacuo. Purification by flash silica chromatography (CH2Cl2/MeOH, 19: 1) yielded TC-DODEG4 (14) as a pale yellow oil (171 mg, 36%). RF 0.40 (CH2Cl2/MeOH, 9: 1); Vmax neatycnT1 2950, 2859, 1740, 1464; NMR (600 MHz; CDCI3) δ 0.83 (t, J = 7.0 Hz, 9H), 1.13-1.22 (m, 64H), 1.51 (m, 4H), 1.57 (m, 2H), 1.92-1.97 (m, 12H), 2.29 (t, J = 7.7 Hz, 2H), 3.38-3.51 (m, 14H), 3.51 (m, 6H), 3.58 (m, 4H), 3.92-4.05 (m, 4H), 4.08 (m, 1H), 4.18 (m, 2H), 5.27 (m, 6H); 13C NMR (150 MHz; CDCI3) δ 14.2, 22.8, 25.0, 26.1, 26.3, 27.26, 27.30, 29.0, 29.1-29.9 (signals superimposed), 30.1, 32.1, 32.7, 34.2, 53.3, 53.4, 63.3, 65.0, 65.2, 66.8, 68.6, 69.29, 69.32, 70.3, 70.4, 70.5, 70.6, 72.1, 73.5, 127.9-130.5 (signals superimposed), 173.9; m/z [HRMS ES+] found [M-Br]+ 1060.9904. CevHnoNO? requires 1060.9847; m/z (+ES) 1061 ([M-Br]+, 100%), 980 (60), 931 (70), 843 (65), 306 (63).
  • 23
  • [ 104162-47-2 ]
  • 2-(2-(2-(bromoethoxy)ethoxy)ethoxy)ethyl acetate [ No CAS ]
  • C51H100NO7(1+)*Br(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% In acetone at 90℃; for 48h; Sealed tube;
  • 24
  • [ 104162-47-2 ]
  • 2-(2-(2-(2-bromoethoxy)ethoxy)ethoxy)ethyl octanoate [ No CAS ]
  • N-(2,3-bis((9Z)-octadecenyloxy)propyl)-N,N-dimethyl-13-oxo-3,6,9,12-tetraoxaicosan-1-aminium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% In acetone at 90℃; for 48h; Sealed tube;
  • 25
  • [ 104162-47-2 ]
  • 2-(2-(2-(2-bromoethoxy)ethoxy)ethoxy)ethyl dodecanoate [ No CAS ]
  • N-(2,3-bis((9Z)-octadecenyloxy)propyl)-N,N-dimethyl-13-oxo-3,6,9,12-tetraoxatetracosan-1-aminium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
19% In acetone at 90℃; for 48h; Sealed tube;
  • 26
  • [ 104162-47-2 ]
  • (9Z)-2-(2-(2-(2-bromoethoxy)ethoxy)ethoxy)ethyl oleate [ No CAS ]
  • N-(2,3-bis((9Z)-octadecenyloxy)propyl)-N,N-dimethyl-13-oxo-3,6,9,12-tetraoxatriacont-(21Z)-en-1-aminium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% In acetone at 90℃; for 48h; Sealed tube;
  • 27
  • [ 104162-47-2 ]
  • (9Z)-2-(2-(2-(5-bromopentanoyloxy)ethoxy)ethoxy)ethyl oleate [ No CAS ]
  • N-(2,3-bis((9Z)-octadecenyloxy)propyl)-N,N-dimethyl-5,16-dioxo-6,9,12,15-tetraoxatritriacont-(24Z)-en-1-aminium bromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
11% In tetrahydrofuran at 90℃; for 48h; Sealed tube;
Same Skeleton Products
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