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[ CAS No. 504-57-4 ] {[proInfo.proName]}

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Product Details of [ 504-57-4 ]

CAS No. :504-57-4 MDL No. :MFCD00009584
Formula : C19H38O Boiling Point : -
Linear Structure Formula :- InChI Key :YUPOCHDBBHTUBJ-UHFFFAOYSA-N
M.W : 282.50 Pubchem ID :10441
Synonyms :

Calculated chemistry of [ 504-57-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.95
Num. rotatable bonds : 16
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 93.65
TPSA : 17.07 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -2.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.83
Log Po/w (XLOGP3) : 8.1
Log Po/w (WLOGP) : 6.84
Log Po/w (MLOGP) : 5.02
Log Po/w (SILICOS-IT) : 7.13
Consensus Log Po/w : 6.38

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 3.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.64
Solubility : 0.000649 mg/ml ; 0.0000023 mol/l
Class : Moderately soluble
Log S (Ali) : -8.32
Solubility : 0.00000137 mg/ml ; 0.0000000048 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -7.08
Solubility : 0.0000237 mg/ml ; 0.0000000839 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.6

Safety of [ 504-57-4 ]

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

Application In Synthesis of [ 504-57-4 ]

* 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 [ 504-57-4 ]

[ 504-57-4 ] Synthesis Path-Downstream   1~100

  • 1
  • [ 50-00-0 ]
  • [ 504-57-4 ]
  • [ 506-59-2 ]
  • [ 102547-27-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride bei Erwaermen des Reaktionsprodukts mit Natriumboranat in wss.-methanol. Natronlauge;
  • 2
  • [ 112-30-1 ]
  • [ 504-57-4 ]
YieldReaction ConditionsOperation in experiment
With chromium(III) oxide at 400℃;
  • 3
  • [ 334-48-5 ]
  • [ 504-57-4 ]
YieldReaction ConditionsOperation in experiment
97% With iron at 250 - 315℃; Inert atmosphere; Dean-Stark; 6 Example 6 - Synthesis of nonadecan-10-one (diketone of C10 capric acid) [00161] The reaction was carried under argon in a 250 mL round bottom flask equipped with mechanical stirring, Dean-Stark apparatus and an addition funnel. In the reactor, 2.0 g (35.8 mmol) of iron powder were dispensed and 50g (290.4 mmol) of capric acid were introduced into the addition funnel. [00162] A first partial amount of 12.5 g of capric acid was added into the reactor and the temperature was brought to 250°C. The mixture was stirred at this temperature during 1 h45. During this time the color of the media changed to black and H2 gas was released. FTIR analysis of the crude mixture showed complete formation of intermediate iron carboxylate. [00163] The temperature was then raised to 315°C and the mixture was stirred during 1 h30 in order to transform the iron carboxlyate complex to ketone, CO2 and iron oxide. [00164] The remaining amount of capric acid (37.5 g) was then slowly added into the reactor during 5h00 at a flow rate which allowed keeping concentration of capric acid in the reaction media very low (no accumulation of free acid in solution). In practise this could be done by the successive slow additions of fractions of 12.5 g of capric acid every 1.5 h. [00165] After the addition of capric acid was completed, the mixture was allowed to stir at 315°C until the intermediate iron complex was not detected anymore by FTIR. [00166] When the reaction was completed, the mixture was allowed to cool down at room temperature and 200 ml_ of CHC were added to the crude media. The mixture was stirred at 40°C in order to solubilize the product (nonadecan-10-one). The obtained suspension was filtered on a silica plug and eluted using 1.5 L of chloroform. Evaporation of the solvent afforded 39.7 g (140.5 mmol) of the product nonadecan-10-one as an analytically pure yellow powder (97% isolated yield).
With thorium dioxide at 375 - 400℃;
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / dichloromethane / 1.5 h 1.2: 3 h 2.1: magnesium / tetrahydrofuran / 1.5 h / Reflux 2.2: 0.5 h / 20 °C
With zirconium(IV) oxide at 400℃; Inert atmosphere; Flow reactor;

  • 4
  • [ 504-57-4 ]
  • [ 2940-26-3 ]
  • [ 102703-36-6 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide
  • 5
  • [ 504-57-4 ]
  • [ 16840-84-9 ]
YieldReaction ConditionsOperation in experiment
95% With sodium tetrahydroborate In tetrahydrofuran; methanol at 0 - 25℃; for 2h; 24.1; 36.1 Step 1: Nonadecan- 10-ol To a solution of nonadecan- 10-one (24 g, 85 mmol) in methanol (300 mL) and THF (1,000 mL) was added NaBH.f (4.82 g, 127 mmol) at 0 °C. The reaction mixture was stirred at 25 °C for 2 h and quenched with slow addition of 200 (mL) sat. NH4CI and concentrated. Then, diluted with H2O (500 mL) and EtOAc (600 mL). The organic phase was separated and the aqueous layer was extracted with EtOAc (200 ml c 2). The combined organic layers were washed with water (200 ml c 2), dried over Na2804 and concentrated to give nonadecan-10-ol (23 g, 81 mmol, 95 % yleld) as white solid which was used in the next step without purification. LCMS: no mass.
95% With sodium tetrahydroborate In tetrahydrofuran; methanol at 0 - 25℃; for 2h; 24.1; 36.1 Step 1: Nonadecan- 10-ol To a solution of nonadecan- 10-one (24 g, 85 mmol) in methanol (300 mL) and THF (1,000 mL) was added NaBH.f (4.82 g, 127 mmol) at 0 °C. The reaction mixture was stirred at 25 °C for 2 h and quenched with slow addition of 200 (mL) sat. NH4CI and concentrated. Then, diluted with H2O (500 mL) and EtOAc (600 mL). The organic phase was separated and the aqueous layer was extracted with EtOAc (200 ml c 2). The combined organic layers were washed with water (200 ml c 2), dried over Na2804 and concentrated to give nonadecan-10-ol (23 g, 81 mmol, 95 % yleld) as white solid which was used in the next step without purification. LCMS: no mass.
With ethanol; nickel at 135℃; Hydrogenation;
With silica gel; nickel at 120℃; Hydrogenation;
With lithium aluminium tetrahydride
With aluminum isopropoxide; isopropyl alcohol
With hydrogen at 150℃;

  • 6
  • [ 504-57-4 ]
  • [ 105-36-2 ]
  • [ 114161-39-6 ]
YieldReaction ConditionsOperation in experiment
With toluene; zinc; benzene Behandeln des Reaktionsprodukts mit aethanol. Kalilauge;
  • 7
  • [ 112-13-0 ]
  • [ 504-57-4 ]
YieldReaction ConditionsOperation in experiment
With diethyl ether; triethylamine und beim Erwaermen des vom Triaethylamin-hydrochlorid befreiten Reaktionsgemisches mit wss.Schwefelsaeure;
  • 8
  • [ 504-57-4 ]
  • [ 105-56-6 ]
  • [ 86274-11-5 ]
YieldReaction ConditionsOperation in experiment
With ammonium acetate; acetic acid; benzene unter Entfernen des gebildeten Wassers;
  • 9
  • [ 58712-53-1 ]
  • [ 504-57-4 ]
YieldReaction ConditionsOperation in experiment
With phenylmagnesium bromide In diethyl ether
  • 10
  • [ 111-66-0 ]
  • [ 112-12-9 ]
  • [ 89185-87-5 ]
  • [ 504-57-4 ]
YieldReaction ConditionsOperation in experiment
With sodium persulfate; silver nitrate In water; acetonitrile for 3h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
  • 11
  • [ 112-30-1 ]
  • [ 504-57-4 ]
  • [ 1654-86-0 ]
YieldReaction ConditionsOperation in experiment
92 % Chromat. at 230℃; for 23h; in liquid phase;
  • 12
  • [ 334-48-5 ]
  • [ 124-11-8 ]
  • [ 112-12-9 ]
  • [ 504-57-4 ]
YieldReaction ConditionsOperation in experiment
With acetic anhydride at 250℃; Yield given. Yields of byproduct given;
  • 13
  • [ 504-57-4 ]
  • [ 111-66-0 ]
  • [ 112-12-9 ]
  • 2-Hexyl-1-nonyl-cyclobutanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
In various solvent(s) at 31℃; for 12h; Irradiation;
  • 14
  • [ 504-57-4 ]
  • [ 105-36-2 ]
  • [ 80303-03-3 ]
YieldReaction ConditionsOperation in experiment
15.6 g With mercury dichloride; zinc In benzene for 4h;
  • 15
  • [ 504-57-4 ]
  • [ 57-14-7 ]
  • 10-Nonadecanon-dimethylhydrazon [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol for 24h; Heating; Yield given;
  • 16
  • [ 111-66-0 ]
  • [ 67-64-1 ]
  • [ 89185-87-5 ]
  • [ 112-12-9 ]
  • [ 504-57-4 ]
  • 5-n-hexyltridecan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With sodium persulfate; silver nitrate In water for 7h; Heating;
  • 17
  • [ 99165-49-8 ]
  • [ 504-57-4 ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride In methanol for 10h; Yield given;
  • 18
  • [ 111-83-1 ]
  • [ 6407-36-9 ]
  • [ 112-12-9 ]
  • [ 504-57-4 ]
YieldReaction ConditionsOperation in experiment
With aluminum oxide; oxalic acid Yield given. Multistep reaction. Yields of byproduct given;
  • 19
  • [ 504-57-4 ]
  • [ 124-68-5 ]
  • [ 174153-10-7 ]
YieldReaction ConditionsOperation in experiment
100% With toluene-4-sulfonic acid In toluene Heating;
YieldReaction ConditionsOperation in experiment
With potassium hydroxide
  • 21
  • [ 112-30-1 ]
  • [ 504-57-4 ]
YieldReaction ConditionsOperation in experiment
at 400℃;
  • 22
  • [ 71-41-0 ]
  • [ 112-30-1 ]
  • [ 31857-89-3 ]
  • [ 504-57-4 ]
YieldReaction ConditionsOperation in experiment
at 400℃;
  • 23
  • [ 504-57-4 ]
  • 2-Nonyl-1-undecene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Yield given. Multistep reaction;
  • 24
  • [ 504-57-4 ]
  • [ 86325-38-4 ]
YieldReaction ConditionsOperation in experiment
95% With pyridine; hydroxylamine hydrochloride In ethanol for 2h; Heating;
91% With pyridine; hydroxylamine hydrochloride In ethanol for 2h; Reflux; 2.2.1 10-Nonadecanamine 10-Nonadecanamine was obtained according to the literature procedure [16]. Briefly, a solution of 500mg (1.77mmol) of 10-nonadecanone in 5ml of ethanol and 3ml of pyridine was treated with 250mg (3.6mmol) of hydroxylamine hydrochloride and then refluxed for 2h. The resulting mixture was then concentrated by evaporation and the residue was partitioned between 5% HCl and hexane. The organic layer was then washed several times with water, dried over MgSO4 and concentrated to yield 480mg of 10-nonadecanone oxime as an oil (91% yield).
  • 25
  • [ 79695-15-1 ]
  • [ 504-57-4 ]
  • [ 922507-60-6 ]
YieldReaction ConditionsOperation in experiment
48% With sodium cyanoborohydride In tetrahydrofuran; methanol at 60℃; for 6h;
  • 26
  • 3-[[6-(2-amino-ethoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl]-(2-methoxycarbonyl-ethyl)-amino]-propionic acid methyl ester [ No CAS ]
  • [ 504-57-4 ]
  • [ 1054627-45-0 ]
YieldReaction ConditionsOperation in experiment
With sodium cyanoborohydride In tetrahydrofuran; methanol at 60℃; for 6h;
  • 27
  • [ 504-57-4 ]
  • [ 120-80-9 ]
  • [ 293305-40-5 ]
YieldReaction ConditionsOperation in experiment
86% With toluene-4-sulfonic acid In toluene Heating;
  • 28
  • [ 504-57-4 ]
  • [ 293305-46-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 86 percent / p-toluenesulfonic acid / toluene / Heating 2: 46 percent / N-bromosuccinimide / dimethylformamide / 20 °C
  • 29
  • [ 504-57-4 ]
  • [ 293305-54-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 86 percent / p-toluenesulfonic acid / toluene / Heating 2: 46 percent / N-bromosuccinimide / dimethylformamide / 20 °C 3: 38 percent / dimethylformamide / 140 °C
  • 30
  • [ 504-57-4 ]
  • [ 922507-62-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 48 percent / NaCNBH3 / methanol; tetrahydrofuran / 6 h / 60 °C 2: 62 percent / 12 h / 20 °C
  • 31
  • [ 504-57-4 ]
  • methyl 6-[(2-carboxyethyl)(1-nonyldecyl)amino]-6-deoxy-α-D-mannopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 48 percent / NaCNBH3 / methanol; tetrahydrofuran / 6 h / 60 °C 2: 62 percent / 12 h / 20 °C 3: 80 percent / LiOH*H2O / propan-2-ol; H2O / 12 h / 20 °C
  • 32
  • [ 504-57-4 ]
  • [ 922507-66-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: NaCNBH3 / methanol; tetrahydrofuran / 6 h / 60 °C 2: pyridine; DMAP / CH2Cl2 / 3 h / 20 °C 3: 159 mg / NaOMe / methanol; CH2Cl2 / 3 h / 0 °C
  • 33
  • [ 504-57-4 ]
  • [ 922507-68-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: NaCNBH3 / methanol; tetrahydrofuran / 6 h / 60 °C 2: pyridine; DMAP / CH2Cl2 / 3 h / 20 °C 3: 159 mg / NaOMe / methanol; CH2Cl2 / 3 h / 0 °C 4: 92 percent / LiOH*H2O / methanol; H2O / 12 h / 0 °C
  • 34
  • [ 504-57-4 ]
  • [ 1053624-45-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: NaCNBH3 / methanol; tetrahydrofuran / 6 h / 60 °C 2: pyridine; DMAP / CH2Cl2 / 3 h / 20 °C
  • 35
  • [ 504-57-4 ]
  • [ 3241-23-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 95 percent / pyridine; hydroxylamine hydrochloride / ethanol / 2 h / Heating 2: 88 percent / sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 2 h / Heating
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; pyridine / ethanol / 2 h / Reflux 2: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 2 h / Reflux
  • 36
  • [ 504-57-4 ]
  • [ 130296-48-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 95 percent / pyridine; hydroxylamine hydrochloride / ethanol / 2 h / Heating 2: 88 percent / sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 2 h / Heating 3: 66 percent / imidazole; zinc acetate / 2 h / 160 °C
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; pyridine / ethanol / 2 h / Reflux 2: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 2 h / Reflux 3: zinc diacetate; quinoline / 4 h / 160 °C / Inert atmosphere
  • 37
  • [ 504-57-4 ]
  • 2-(1-hydroxy-2-methylpropan-2-yl)-3,3-dinonyloxaziridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 100 percent / p-TsOH / toluene / Heating 2: m-chloroperbenzoic acid, p-TsOH / diethyl ether / 1 h / Ambient temperature
  • 38
  • [ 504-57-4 ]
  • 4,4-dimethyl-2,2-dinonyloxazolidine-N-oxyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 100 percent / p-TsOH / toluene / Heating 2: 70 percent / m-chloroperbenzoic acid / diethyl ether / 1 h / 0 °C
  • 39
  • [ 111-66-0 ]
  • [ 504-57-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 68 percent / AgNO3, Na2S2O8 / H2O / 7 h / Heating 2: AgNO3, Na2S2O8 / H2O; acetonitrile / 3 h / Heating
  • 40
  • [ 110-38-3 ]
  • [ 504-57-4 ]
  • 41
  • [ 89638-16-4 ]
  • [ 504-57-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diethyl ether; tetrahydrofuran / 58 h / Heating 2: KF / methanol / 10 h
  • 42
  • [ 504-57-4 ]
  • [ 111-66-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: various solvent(s) / 12 h / 31 °C / Irradiation 2: various solvent(s) / Irradiation
  • 43
  • [ 504-57-4 ]
  • 2-Hexyl-1-methyl-cyclobutanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: various solvent(s) / 12 h / 31 °C / Irradiation 2: various solvent(s) / Irradiation
  • 44
  • [ 504-57-4 ]
  • [ 90255-46-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: ethanol / 24 h / Heating 2: 93 percent / anhydrous N2H4 / ethanol / 24 h / Heating
  • 45
  • [ 504-57-4 ]
  • [ 80256-62-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 15.6 g / Zn, mercury chloride / benzene / 4 h 2: 1.) formic acid; 2.) H2 / 5 percent Pd/C / 1.) 3 h, reflux; 2.) rt 3: LiAlH4 / diethyl ether / 2 h / Heating
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere 1.2: 18 h / 20 °C / Reflux; Inert atmosphere 2.1: hydrogen; platinum(IV) oxide / chloroform; methanol / 23 h / 20 °C / 760.05 Torr / Inert atmosphere 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere 3.2: Celite® / 18 h / 0 - 20 °C / Inert atmosphere
  • 46
  • [ 504-57-4 ]
  • ethyl 3-nonyldodecanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 15.6 g / Zn, mercury chloride / benzene / 4 h 2: 1.) formic acid; 2.) H2 / 5 percent Pd/C / 1.) 3 h, reflux; 2.) rt
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 1.2: 20 °C / Reflux 2.1: hydrogen / platinum(IV) oxide / chloroform; methanol / 23 h / 760.05 Torr
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere 1.2: 18 h / 20 °C / Reflux; Inert atmosphere 2.1: hydrogen; platinum(IV) oxide / chloroform; methanol / 23 h / 20 °C / 760.05 Torr / Inert atmosphere
  • 47
  • [ 504-57-4 ]
  • [ 115207-22-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: aq.-ethanolic KOH 2: Raney nickel / Hydrogenation.anschliessende Oxidation mit Na2Cr2O7 3: zinc; acetic acid
  • 48
  • [ 504-57-4 ]
  • [ 113550-13-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aq.-ethanolic KOH 2: Raney nickel / Hydrogenation.anschliessende Oxidation mit Na2Cr2O7
  • 49
  • [ 504-57-4 ]
  • 10-chloro-nonadecane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aluminium isopropylate; isopropyl alcohol 2: petroleum ether; phosphorus (V)-chloride
Multi-step reaction with 2 steps 1: H2 / Raney-Ni / 150 °C / 152000 Torr 2: SOCl2, Py
  • 50
  • [ 504-57-4 ]
  • [ 123936-58-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: nickel; silica gel / 120 °C / Hydrogenation 2: glacial acetic acid; chlorosulfonic acid
  • 51
  • [ 504-57-4 ]
  • [1]naphthyl-carbamic acid-(1-nonyl-decyl ester) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: nickel; silica gel / 120 °C / Hydrogenation
  • 52
  • [ 504-57-4 ]
  • [ 119621-19-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aq.-ethanolic hydrochloric acid / bei Erwaermen des Reaktionsprodukts mit Natriumboranat in wss.-methanol. Natronlauge
  • 53
  • [ 504-57-4 ]
  • 2,2-dinonyl-succinic acid-anhydride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: benzene; ammonium acetate; acetic acid / unter Entfernen des gebildeten Wassers 2: aqueous ethanol / Erhitzen des Reaktionsprodukts mit Essigsaeure und wss. Schwefelsaeure und anschliessend mit wss. Kalilauge und Erwaermen der erhaltenen Saeure mit Acetylchlorid
  • 54
  • bis(μ,η2-decanoyl)hexacarbonyldiiron [ No CAS ]
  • [ 13463-40-6 ]
  • [ 504-57-4 ]
YieldReaction ConditionsOperation in experiment
1: 46% 2: 73% With methyl iodide In cyclohexane byproducts: n-nonyl iodide, n-decane, CH3COC9H19; (N2); added n-tridecane, methyl iodide and cyclohexane to Fe-complex; stirred at room temp. for 3 h; cooled to -78°C; IR, GLPC, HPLC;
  • 55
  • bis(μ,η2-decanoyl)hexacarbonyldiiron [ No CAS ]
  • [ 14649-69-5 ]
  • [ 504-57-4 ]
YieldReaction ConditionsOperation in experiment
1: 54% 2: 98% With triphenylphosphine In cyclohexane byproducts: Fe(CO)3(P(C6H5)3)2, Fe3(CO)12; (N2); added a soln. of triphenyl phosphine, n-tridecane and cyclohexane to Fe-complex; stirred for 2 h at room temp.; cooled to -78°C; IR, GLPC, HPLC;
  • 56
  • [ 693-58-3 ]
  • [ 254963-75-2 ]
  • [ 504-57-4 ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: 1-Bromononane With magnesium In tetrahydrofuran for 1.5h; Reflux; Stage #2: N-methoxy-N-methyldecanoylamide In tetrahydrofuran at 20℃; for 0.5h; D-1-2 Polished shaved magnesium (3.2 g, 134 mmol) was heated, and thereafter, an anhydrous THF solution (68 ml) of 1-bromononane (12.9 ml, 67.5 mmol) was slowly added dropwise thereto. After heating to reflux for 1.5 hours, the reaction solution was cooled to a room temperature, and it was then added dropwise to a THF (80 mL) solution of the N-methoxy-N-methyldecanamide (4.8 g, 22.5 mmol) obtained by the method described in Production Example D-1-1. After the obtained mixture had been stirred for 30 minutes, 1 N hydrochloric acid was added to the reaction solution, followed by extraction with diethyl ether two times. Anhydrous magnesium sulfate was added to the organic layer to dry it, and the resultant was filtrated and was then concentrated. The obtained residue was purified using column chromatography (hexane : dichloromethane = 8 : 1), so as to obtain 10-nonadecanone (6.0 g, 95%) as a ketone body in the form of a white amorphous solid. colorless solid; FT IR (neat) 2953, 2916, 2847, 1698 cm-1; 1H NMR (300 MHz inCDCl3) δ0.88 (6H, t, J = 6.9 Hz), 1.26 (24H, m), 1.55 (4H, m), 2.38 (4H, t, J = 7.5 Hz); 13C NMR (75 MHz in CDCl3) δ14.03, 22.63, 23.84, 29.24, 29.41, 31.84,42.74, 211.49; CIMS m/z (%) 282 (M+); HRMS (CI+) m/z calcd for C19H38O (M+) 282.2882, Found 282.2902.
  • 57
  • [ 867-13-0 ]
  • [ 504-57-4 ]
  • [ 1223421-30-4 ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: 10-Nonadecanon In tetrahydrofuran; mineral oil at 20℃; Reflux; D-1-3 Sodium hydride (60 w/w %, 6 g, 142 mmol) was dissolved in anhydrous THF (200 ml), and the obtained mixture was then cooled to 0°C. Ethyl diethylphosphonoacetate (34 ml, 171 mmol) was added dropwise to the reaction solution, and the obtained mixture was then stirred for 30 minutes. Thereafter, the temperature of the obtained reaction solution was increased to a room temperature, and the 10-nonadecanone (6.0 g, 21.3 mmol) obtained by the method described in Production Example D-1-2 was then added to the reaction solution. The obtained mixture was further heated to reflux for 18 hours. Thereafter, distilled water was added to the reaction solution, followed by extraction with diethyl ether two times. Anhydrous magnesium sulfate was added to the organic layer to dry it, and the resultant was filtrated and was then concentrated. The obtained residue was purified using column chromatography (hexane : dichloromethane = 6 : 1), so as to obtain ethyl 3-nonyl-2-dodecanoate (7.6 g, 99%) as an ester form in the form of a colorless transparent liquid. colorless oil; FT IR (neat) 2928, 2855, 1718 cm-1 ; 1H NMR (300 MHz in CDCl3) δ0.88 (6H, t, J = 6.9 Hz), 1.27 (27H, m), 1.44 (4H, m), 2.12 (2H, t, J = 7.8 Hz), 2.58 (2H, t, J = 8.1 Hz), 4.14 (2H, q, J = 7.2 Hz), 5.61 (1H, br s); 13C NMR (75 MHz in CDCl3) δ14.14, 14.35, 22.70, 27.68, 28.75, 29.34, 29.49, 29.52, 29.60, 30.01, 31.92, 32.19, 38.44, 59.42, 114.98, 165.07, 166.66; CIMS m/z (%) 352 (M+) ; HRMS (CI+) m/z calcd for C23H44O2 (M+) 352.3349, Found 352.3345.
99% Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere; Stage #2: 10-Nonadecanon In tetrahydrofuran; mineral oil at 20℃; for 18h; Reflux; Inert atmosphere;
  • 58
  • [ 504-57-4 ]
  • 3-nonyldodecanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 1.2: 20 °C / Reflux 2.1: hydrogen / platinum(IV) oxide / chloroform; methanol / 23 h / 760.05 Torr 3.1: potassium hydroxide; water / butan-1-ol / 4.5 h / Reflux
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere 1.2: 18 h / 20 °C / Reflux; Inert atmosphere 2.1: hydrogen; platinum(IV) oxide / chloroform; methanol / 23 h / 20 °C / 760.05 Torr / Inert atmosphere 3.1: potassium hydroxide / butan-1-ol; water / 4.5 h / 100 °C / Inert atmosphere
  • 59
  • [ 18198-76-0 ]
  • [ 1264-57-9 ]
  • hentriaconta-7<i>c</i>(?),24<i>c</i>(?)-dien-16-one [ No CAS ]
  • [ 373-49-9 ]
  • [ 334-48-5 ]
  • [ 504-57-4 ]
  • C25H48O [ No CAS ]
  • 60
  • [ 1763-10-6 ]
  • [ 1264-57-9 ]
  • [ 334-48-5 ]
  • [ 504-57-4 ]
  • [ 502-73-8 ]
  • [ 31469-37-1 ]
  • [ 57-10-3 ]
YieldReaction ConditionsOperation in experiment
With OleA from Xanthomonas campestris spv. campestris str. ATCC 33913 at 20℃; for 0.0833333h; aq. buffer; Enzymatic reaction;
  • 61
  • [ 1264-57-9 ]
  • [ 143-07-7 ]
  • [ 334-48-5 ]
  • [ 504-57-4 ]
  • [ 22026-16-0 ]
  • [ 540-09-0 ]
YieldReaction ConditionsOperation in experiment
With OleA from Xanthomonas campestris spv. campestris str. ATCC 33913 at 20℃; for 0.0833333h; aq. buffer; Enzymatic reaction;
  • 62
  • [ 1264-57-9 ]
  • [ 334-48-5 ]
  • [ 504-57-4 ]
YieldReaction ConditionsOperation in experiment
With OleA from Xanthomonas campestris spv. campestris str. ATCC 33913 at 20℃; for 0.0833333h; aq. acetate buffer; Enzymatic reaction;
  • 63
  • [ 1264-57-9 ]
  • myristoyl-coenzyme A [ No CAS ]
  • [ 334-48-5 ]
  • [ 504-57-4 ]
  • [ 39754-76-2 ]
  • [ 542-50-7 ]
  • [ 544-63-8 ]
YieldReaction ConditionsOperation in experiment
With OleA from Xanthomonas campestris spv. campestris str. ATCC 33913 at 20℃; for 0.0833333h; aq. buffer; Enzymatic reaction;
  • 64
  • [ 504-57-4 ]
  • [ 1416474-23-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere 1.2: 18 h / 20 °C / Reflux; Inert atmosphere 2.1: hydrogen; platinum(IV) oxide / chloroform; methanol / 23 h / 20 °C / 760.05 Torr / Inert atmosphere 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere 3.2: Celite® / 18 h / 0 - 20 °C / Inert atmosphere 4.1: dmap; triethylamine; toluene-4-sulfonic acid / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere
  • 65
  • [ 504-57-4 ]
  • [ 1463-10-1 ]
  • [ 1440632-40-5 ]
YieldReaction ConditionsOperation in experiment
83% With hydrogenchloride; orthoformic acid triethyl ester; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; at 20℃; for 24h; Anhydrous methyluridine (29; 0.77 g, 3 mmol) was dissolved in dry DMF (10 ml). Then, nonadecan-10-one (1.13 g, 4 mmol), dissolved in CH2Cl2 (10 ml), triethylorthoformate (1 ml), and 4 M HCl in 1,4-dioxane (4 ml) were added. The mixture was stirred at room temp. for 24 h. Subsequently, the mixture was partinioned between an aq. sat. Na2CO3 soln. (100 ml) and CH2Cl2 (100 ml). The organic phase was separated, dried over Na2SO4, filtered and evaporated to dryness. Traces of DMF were removed by repeated evaporation from CH2Cl2. The residue was dried in high vacuo overnight. The resulting colourless foam was purified by chromatography (silica gel 60, column: 6.5 x 10 cm). Elution with CH2Cl2/MeOH, 95:5 (v/v) gave one main zone which was pooled, the solvent was evaporated, and the residue was dried in high vacuo. Colourless oil (1.3 g, 83%). TLC (silica gel 60, CH2Cl2/MeOH, 95:5, (v/v)): Rf, 0.31. UV(MeOH): lambdamax = 265 nm (epsilon = 10600 M-1 cm-1). Anal. calc. for C29H50N2O6 (522,73): C, 66.63; H, 9.64; N, 5.36. Found: C, 66.47; H, 9.272; N, 5.25. 1H-NMR (DMSO-d6): 11.34 (s, H-N(3)); 7.63 (s, H-C(6)); 5.83 (d, 3J(H-C(1'),H-C(2') = 2.5, H-C(1')); 5.02 (t, 3J(OH-C(5'), H2-C(5')) = 5.0, (OH-C(5')); 4.88 (dd, 3J (H-C(2'),H-C(1') = 3.0, 3J (H-C(2'), H-C(3') = 6.5, H-C(2')); 4.75 (dd, 3J(H-C(3'), H-C(2') = 6.5; 3J(H-C(3'),H-C(4') = 3.5, H-C(3')); 4.02 (m, 3J(H-C(4'), H-C(3') = 3.5; 3J (H-C(4'), H2C(5') = 4.5, H-C(4')); 3.56 (m, H2-C(5')); 1.76 (s, 3H, CH3); 1.66 (m, H2(endo)-C(1a")); 1.52 (m, H2(exo)-C(1b")); 1.38 (m, H2(endo)-C(2a")); 1.24 (m, 6xH2(endo)-C(3a"-8a"), 7xH2(exo)-C(2b"-8b"), 26H); 0.85 (m, 2xH3-C(9a", 9b"), 6H). 13C-NMR (DMSO-d6): delta. 163.66 (C(4)); 150.27 (C(2)); 137.50 (C(6)); 116.77 (C(acetal)); 109.38 (C(5)); 90.52 (C(1')); 86.24 (C(4')); 83.50 (C(3')); 80.58 (C(2')); 61.31 (C(5')); 36.33 (C(1a")); 36.28 (C(1b")); 31.17 (C(7a")); 31.16 (C(7b")); 29.06 (C(3a")); 29.01 (C(3b")); 28.83 (C(4a")); 28.81 (C(4b")); 28.80 (C(5")); 28.77 (C(6a")); 28.55 (C(6b")); 23.48 (C(2a")); 22.86 (C(2b")); 21.97 (C(8a")); 21.96 (C(8b")); 13.82 (C(9a")); 13.81 (C(9b")); 11.94 (CH3-(base)).
83% With hydrogenchloride; orthoformic acid triethyl ester; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; at 20℃; for 24h; Anhydrous methyluridine (29; 0.77 g, 3 mmol) was dissolved in dry DMF (10 ml). Then, nonadecan-10-one (1.13 g, 4 mmol), dissolved in CH2Cl2 (10 ml), triethylorthoformate (1 ml), and 4 M HCl in 1,4-dioxane (4 ml) were added. The mixture was stirred at room temp. for 24 h. Subsequently, the mixture was partitioned between an aq. sat. Na2CO3 soln. (100 ml) and CH2Cl2 (100 ml). The organic phase was separated, dried over Na2SO4, filtered and evaporated to dryness. Traces of DMF were removed by repeated evaporation from CH2Cl2. The residue was dried in high vacuo overnight. The resulting colourless foam was purified by chromatography (silica gel 60, column: 6.5*10 cm). Elution with CH2Cl2/MeOH, 95:5 (v/v) gave one main zone which was pooled, the solvent was evaporated, and the residue was dried in high vacuo. Colourless oil (1.3 g, 83%). TLC (silica gel 60, CH2Cl2/MeOH, 95:5, (v/v)): Rf, 0.31. UV(MeOH): lambdamax=265 nm (E=10600 M-1 cm-1). Anal. calc. for C29H50N2O6 (522.73): C, 66.63; H, 9.64; N, 5.36. Found: C, 66.47; H, 9.272; N, 5.25. 1H-NMR (DMSO-d6): 11.34 (s, H-N(3)); 7.63 (s, H-C(6)); 5.83 (d, 3J(H-C(1'), H-C(2')=2.5, H-C(1')); 5.02 (t, 3J(OH-C(5'), H2-C(5'))=5.0, (OH-C(5')); 4.88 (dd, 3J (H-C(2'), H-C(1')=3.0, 3J (H-C(2'), H-C(3')=6.5, H-C(2')); 4.75 (dd, 3J(H-C(3'), H-C(2')=6.5; 3J(H-C(3'), H-C(4')=3.5, H-C(3')); 4.02 (m, 3J(H-C(4'), H-C(3')=3.5; 3J (H-C(4'), H2C(5')=4.5, H-C(4')); 3.56 (m, H2-C(5')); 1.76 (s, 3H, CH3); 1.66 (m, H2(endo)-C(1a")); 1.52 (m, H2(exo)-C(1b")); 1.38 (m, H2(endo)-C(2a")); 1.24 (m, 6*H2(endo)-C(3a"-8a"), 7*H2(exo)-C(2b"-8b"), 26H); 0.85 (m, 2*H3-C(9a", 9b"), 6H). 13C-NMR (DMSO-d6): delta. 163.66 (C(4)); 150.27 (C(2)); 137.50 (C(6)); 116.77 (C(acetal)); 109.38 (C(5)); 90.52 (C(1')); 86.24 (C(4')); 83.50 (C(3')); 80.58 (C(2')); 61.31 (C(5')); 36.33 (C(1a")); 36.28 (C(1b")); 31.17 (C(7a")); 31.16 (C(7b")); 29.06 (C(3a")); 29.01 (C(3b")); 28.83 (C(4a")); 28.81 (C(4b")); 28.80 (C(5")); 28.77 (C(6a")); 28.55 (C(6b")); 23.48 (C(2a")); 22.86 (C(2b")); 21.97 (C(8a")); 21.96 (C(8b")); 13.82 (C(9a")); 13.81 (C(9b")); 11.94 (CH3-(base)).
  • 66
  • [ 504-57-4 ]
  • [ 58-96-8 ]
  • [ 1440631-78-6 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide at 20℃; for 24h;
95% With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide at 20℃; for 24h; 1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dinonyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidin-2,4(1H,3H)-dione (25b). Uridine (24; 0.76 g, 3.1 mmol) was dissolved in anhydr. DMF (10 ml), and nonadecan-10-one (1.11 g, 3.9 mmol), 4 M HCl in 1,4-dioxane (4 ml) and triethylortho formate (1 ml) as well as CH2Cl2 (6 ml) were added consecutively. The reaction mixture was stirred for 24 h at room temp. Subsequently, the mixture was partitioned between an aq. sat. NaHCO3 soln (100 ml) and CH2Cl2 (100 ml). The organic layer was washed with dest. H2O (100 ml), separated, dried over Na2SO4, and then evaporated to dryness. Purification of the raw product was performed by stepped gradient column chromatography (silica gel 60, column: 6.5 x 10 cm). A stepwise elution with 800 ml CH2Cl2/MeOH (99:1, v/v), followed by 200 ml of CH2Cl2/ MeOH (95:5, v/v) gave one main zone from which compd. 25b (1.50 g, 2.95 mmol, 95%) was isolated as a colourless foam, obtained upon evaporation and drying in high vacuo. TLC (silica gel 60; CH2Cl2/MeOH 95:5 (v/v)): Rf, 0.21. UV(MeOH): λmax = 260 nm (ε = 9.600 M-1cm-1). M.p.: 69.8°C. Anal. calc. for C28H48N2O6 (508.69) C, 66.11; H, 9.51; N, 5.51. Found:C, 65.86; H, 9.50; N, 5.21. 1H-NMR (500.13 MHz, DMSO-d6): 11.33 (s, H-N(3)); 7.76 (d, 3J(H-C(6), H-C(5)) = 8.0, H-C(6)); 5.82 (d, 3J(H-C(1'), H-C(2')) = 2.5, H-C(1')); 5.62 (d, 3J(H-C(5), H-C(6)) = 8.0, H-C(5)); 5.02 (m, HO-C(5')); 4.89 (dd, 3J(H-C(2'), H-C(1')) = 2.5, 3J(H-C(2'), H-C(3')) = 6.5, H-C(2')); 4.73 (dd, 3J(H-C(3'), H-C(4')) = 3.5, 3J(H-C(3'), H-C(2')) = 6.5, H-C(3')); 4.05 (q, 2x3J(H-C(4'), H2-C(5')) = 4.2, 3J(H-C(4'), H-C(3')) = 4.2, H-C(4')); 3.57 (m, H2-C(5')); 1.66 (m, H2(endo)-C(1a")); 1.51 (m, H2(exo)-C(1b")); 1.30-1.20 (m, 7xH2(endo)-C(2a"-8a"), 7xH2(exo)-C(2b"-8b"), 28H); 0.85 (m, 2xH3-C(9a", 9b"), 6H). 13C-NMR (125.76 MHz, DMSO-d6): δ. 163.11 (C(4)); 150.28 (C(2)); 141.98 (C(6)); 116.63 (C(acetal)); 101.67 (C(5)); 91.23 (C(1')); 86.69 (C(4')); 83.82 (C(3')); 80.70 (C(2')); 61.35 (C(5')); 36.38 (C(1a")); 36.29 (C(1b")); 31.21 (C(7a")); 31.19 (C(7b")); 29.09 (C(3a")); 29.04 (C(3b")); 28.86 (C(4a")); 28.83 (C(4b")); 28.80 (C(5")); 28.59 (C(6a")); 28.58 (C(6b")); 23.52 (C(2a")); 22.88 (C(2b")); 22.01 (C(8a")); 22.00 (C(8b")); 13.85 (C(9")).
95% With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane at 20℃; for 24h; 1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dinonyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidin-2,4(1H,3H)-dione (25b) Uridine (24; 0.76 g, 3.1 mmol) was dissolved in anhydr. DMF (10 ml), and nonadecan-10-one (1.11 g, 3.9 mmol), 4 M HCl in 1,4-dioxane (4 ml) and triethylortho formate (1 ml) as well as CH2Cl2 (6 ml) were added consecutively. The reaction mixture was stirred for 24 h at room temp. Subsequently, the mixture was partitioned between an aq. sat. NaHCO3 soln (100 ml) and CH2Cl2 (100 ml). The organic layer was washed with dest. H2O (100 ml), separated, dried over Na2SO4, and then evaporated to dryness. Purification of the raw product was performed by stepped gradient column chromatography (silica gel 60, column: 6.5*10 cm). A stepwise elution with 800 ml CH2Cl2/MeOH (99:1, v/v), followed by 200 ml of CH2Cl2/MeOH (95:5, v/v) gave one main zone from which compd. 25b (1.50 g, 2.95 mmol, 95%) was isolated as a colourless foam, obtained upon evaporation and drying in high vacuo. TLC (silica gel 60; CH2Cl2/MeOH 95:5 (v/v)): Rf, 0.21. UV(MeOH): λmax=260 nm (ε=9.600 M-1 cm-1). M.p.: 69.8° C. Anal. calc. for C28H48N2O6 (508.69) C, 66.11; H, 9.51; N, 5.51. Found: C, 65.86; H, 9.50; N, 5.21. 1H-NMR (500.13 MHz, DMSO-d6): 11.33 (s, H-N(3)); 7.76 (d, 3J(H-C(6), H-C(5))=8.0, H-C(6)); 5.82 (d, 3J(H-C(1'), H-C(2'))=2.5, H-C(1')); 5.62 (d, 3J(H-C(5), H-C(6))=8.0, H-C(5)); 5.02 (m, HO-C(5')); 4.89 (dd, 3J(H-C(2'), H-C(1'))=2.5, 3J(H-C(2'), H-C(3'))=6.5, H-C(2')); 4.73 (dd, 3J(H-C(3'), H-C(4'))=3.5, 3J(H-C(3'), H-C(2'))=6.5, H-C(3')); 4.05 (q, 2*3J(H-C(4'), H2-C(5'))=4.2, 3J(H-C(4'), H-C(3'))=4.2, H-C(4')); 3.57 (m, H2-C(5')); 1.66 (m, H2(endo)-C(1a")); 1.51 (m, H2(exo)-C(1b")); 1.30-1.20 (m, 7*H2(endo)-C(2a"-8a"), 7*H2(exo)-C(2b"-8b"), 28H); 0.85 (m, 2*H3-C(9a", 9b"), 6H). 13C-NMR (125.76 MHz, DMSO-d6): δ. 163.11 (C(4)); 150.28 (C(2)); 141.98 (C(6)); 116.63 (C(acetal)); 101.67 (C(5)); 91.23 (C(1')); 86.69 (C(4')); 83.82 (C(3')); 80.70 (C(2')); 61.35 (C(5')); 36.38 (C(1a")); 36.29 (C(1b")); 31.21 (C(7a")); 31.19 (C(7b")); 29.09 (C(3a")); 29.04 (C(3b")); 28.86 (C(4a")); 28.83 (C(4b")); 28.80 (C(5")); 28.59 (C(6a")); 28.58 (C(6b")); 23.52 (C(2a")); 22.88 (C(2b")); 22.01 (C(8a")); 22.00 (C(8b")); 13.85 (C(9")).
  • 67
  • [ 504-57-4 ]
  • [ 1440632-26-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogenchloride; orthoformic acid triethyl ester / dichloromethane; N,N-dimethyl-formamide; 1,4-dioxane / 24 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere; Darkness
  • 68
  • [ 504-57-4 ]
  • [ 1440632-35-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogenchloride; orthoformic acid triethyl ester / dichloromethane; N,N-dimethyl-formamide; 1,4-dioxane / 24 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere; Darkness 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.28 h / 20 °C / Inert atmosphere
  • 69
  • [ 504-57-4 ]
  • [ 1440632-60-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogenchloride; orthoformic acid triethyl ester / dichloromethane; N,N-dimethyl-formamide; 1,4-dioxane / 24 h / 20 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.28 h / 20 °C / Inert atmosphere
  • 70
  • [ 504-57-4 ]
  • [ 1440632-75-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogenchloride; orthoformic acid triethyl ester / dichloromethane; N,N-dimethyl-formamide; 1,4-dioxane / 24 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 24 h / Inert atmosphere; Darkness
  • 71
  • [ 504-57-4 ]
  • [ 1440632-84-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogenchloride; orthoformic acid triethyl ester / dichloromethane; N,N-dimethyl-formamide; 1,4-dioxane / 24 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 24 h / Inert atmosphere; Darkness 3: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.28 h / 20 °C / Inert atmosphere
  • 72
  • [ 504-57-4 ]
  • [ 1440632-11-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogenchloride; orthoformic acid triethyl ester / dichloromethane; N,N-dimethyl-formamide; 1,4-dioxane / 24 h / 20 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.28 h / 20 °C / Inert atmosphere
  • 73
  • [ 504-57-4 ]
  • [ 1189046-71-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydroxylamine hydrochloride; pyridine / ethanol / 2 h / Reflux 2: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 2 h / Reflux 3: zinc diacetate; quinoline / 4 h / 160 °C / Inert atmosphere 4: bromine / dichloromethane / 4 h / 60 °C
  • 74
  • [ 504-57-4 ]
  • [ 316-46-1 ]
  • [ 1581758-36-2 ]
YieldReaction ConditionsOperation in experiment
68% With hydrogenchloride; orthoformic acid triethyl ester; In 1,4-dioxane; N,N-dimethyl-formamide; at 20℃; for 48h; Anhydrous <strong>[316-46-1]5-<strong>[316-46-1]fluorouridine</strong></strong> (1a, 1.0 g, 3.82 mmol) was dissolved in anhydr. DMF (15 ml) and nonadecan-10-one (2.16 g, 7.64 mmol) was added. After addition of HC(OEt)3 (1.0 g, 5.73 mmol) and 4M HCl in 1,4-dioxane (3.4 ml) the reaction mixture was stirred for 48 h at room temperature. Then the mixture was partitioned between CHCl3 (350 ml) and a sat. aq. NaHCO3 soln. (50 ml). The organic layer was washed three times with water (100 ml, each), and the aq. layers were re-extracted with CH2Cl2 (25 ml). The combined organic phases were dried (Na2SO4), filtered and evaporated. The residue was dried over night in high vacuum and then chromatographed (silica gel, column: 6 x 12 cm, CH2Cl2/MeOH, 95:5, v/v) to give compound 19c (1.38 g, 68 %) as a colourless oil. TLC (silica gel, CH2Cl2/MeOH, 95:5, v/v): Rf 0.56. UV (MeOH): lambdamax, 265 nm (epsilon, 9.860 M-1cm-1). Anal. calc. for C28H47FN2O6 (526.681): C, 63.85; H, 8.99; N, 5.32. Found: C, 63.78; H, 8.80; N, 5.15.
  • 75
  • [ 504-57-4 ]
  • [ 316-46-1 ]
  • 5-fluoro-1-[(3aR,4R,6R,6aR)-tetrahydro-6-(hydroxymethyl)-2,2-dinonylfuro[3,4-d][1,3]dioxol-4-yl]pyrimidine-2,4(1H,3H)-dione [ No CAS ]
  • 76
  • [ 504-57-4 ]
  • [ 1581758-40-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: orthoformic acid triethyl ester; hydrogenchloride / N,N-dimethyl-formamide; 1,4-dioxane / 48 h / 20 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.25 h / 20 °C / Inert atmosphere
  • 77
  • [ 504-57-4 ]
  • [ 1590381-23-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: orthoformic acid triethyl ester; hydrogenchloride / N,N-dimethyl-formamide; 1,4-dioxane / 48 h / 20 °C 2: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 °C / Cooling with ice; Inert atmosphere; Darkness
  • 78
  • [ 504-57-4 ]
  • [ 58-96-8 ]
  • [ 1440632-26-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: orthoformic acid triethyl ester; hydrogenchloride / N,N-dimethyl-formamide; dichloromethane; 1,4-dioxane / 24 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere; Darkness
Multi-step reaction with 2 steps 1: hydrogenchloride; orthoformic acid triethyl ester / 1,4-dioxane / 24 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere; Darkness
  • 79
  • [ 504-57-4 ]
  • [ 1463-10-1 ]
  • [ 1440632-75-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: orthoformic acid triethyl ester; hydrogenchloride / N,N-dimethyl-formamide; dichloromethane; 1,4-dioxane / 24 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere; Darkness
Multi-step reaction with 2 steps 1: hydrogenchloride; orthoformic acid triethyl ester / N,N-dimethyl-formamide; dichloromethane; 1,4-dioxane / 24 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 24 h / Inert atmosphere; Darkness
  • 80
  • [ 334-48-5 ]
  • [ 111-84-2 ]
  • [ 629-92-5 ]
  • [ 504-57-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogen at 400℃;
  • 81
  • [ 1073-31-0 ]
  • [ 504-57-4 ]
  • C25H38OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With potassium hydroxide In ethanol for 3h; Inert atmosphere; Reflux;
  • 82
  • [ 504-57-4 ]
  • C25H36I2OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / ethanol / 3 h / Inert atmosphere; Reflux 2: iodine; bis-[(trifluoroacetoxy)iodo]benzene / dichloromethane / 24 h / 20 °C / Inert atmosphere; Darkness
  • 83
  • [ 504-57-4 ]
  • C33H42OS3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium hydroxide / ethanol / 3 h / Inert atmosphere; Reflux 2: iodine; bis-[(trifluoroacetoxy)iodo]benzene / dichloromethane / 24 h / 20 °C / Inert atmosphere; Darkness 3: bis-triphenylphosphine-palladium(II) chloride / toluene / 6 h / 110 °C / Inert atmosphere
  • 84
  • [ 504-57-4 ]
  • C33H40I2OS3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium hydroxide / ethanol / 3 h / Inert atmosphere; Reflux 2: iodine; bis-[(trifluoroacetoxy)iodo]benzene / dichloromethane / 24 h / 20 °C / Inert atmosphere; Darkness 3: bis-triphenylphosphine-palladium(II) chloride / toluene / 6 h / 110 °C / Inert atmosphere 4: iodine; bis-[(trifluoroacetoxy)iodo]benzene / dichloromethane / 24 h / 20 °C / Inert atmosphere; Darkness
  • 85
  • [ 504-57-4 ]
  • C31H40N2OS3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium hydroxide / ethanol / 3 h / Inert atmosphere; Reflux 2: iodine; bis-[(trifluoroacetoxy)iodo]benzene / dichloromethane / 24 h / 20 °C / Inert atmosphere; Darkness 3: bis-triphenylphosphine-palladium(II) chloride / toluene / 6 h / 110 °C / Inert atmosphere
  • 86
  • [ 504-57-4 ]
  • C31H38Br2N2OS3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium hydroxide / ethanol / 3 h / Inert atmosphere; Reflux 2: iodine; bis-[(trifluoroacetoxy)iodo]benzene / dichloromethane / 24 h / 20 °C / Inert atmosphere; Darkness 3: bis-triphenylphosphine-palladium(II) chloride / toluene / 6 h / 110 °C / Inert atmosphere 4: N-Bromosuccinimide / chloroform / 6 h / 70 °C / Inert atmosphere
  • 87
  • [ 504-57-4 ]
  • [ 54-25-1 ]
  • 2-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dinonyltetrahydrofuro[3,4-d] [1,3]dioxol-4-yl]-1,2,4-triazine-3,5(2H,4H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide at 20℃; for 75h;
  • 88
  • [ 334-48-5 ]
  • [ 504-57-4 ]
  • [ 31035-07-1 ]
YieldReaction ConditionsOperation in experiment
With titanium(IV) dioxide at 300 - 450℃;
  • 89
  • [ 504-57-4 ]
  • [ 58-63-9 ]
  • 9-(6-hydroxymethyl-2,2-dinonyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-1,9-dihydropurin-6-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; N,N-dimethyl-formamide at 20℃;
  • 90
  • [ 504-57-4 ]
  • [ 58-61-7 ]
  • 6-(6-aminopurin-9-yl)-2,2-dinonyltetrahydrofuro[3,4-d][1,3]dioxol-4-ylmethanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; N,N-dimethyl-formamide at 20℃;
  • 91
  • [ 504-57-4 ]
  • [ 120379-76-2 ]
  • tert-butyldimethyl[(4-nonyl-3-tridecen-1-yl)oxy]silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.16 g Stage #1: [3-[(tert-butyldimethylsilyl)oxy]propyl]triphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran at 45℃; for 0.5h; Inert atmosphere; Stage #2: 10-Nonadecanon In tetrahydrofuran for 21h; Reflux; 5.3 (3) Synthesis of tert-butyldimethyl[(4-nonyl-3-tridecen-1-yl)oxy]silane The compound (4.38 g, 8.50 mmol) obtained in Production Example 5-(2) was dissolved in 28 THF (15 mL) and in a nitrogen atmosphere, a 29 sodium bis(trimethylsilyl)amide/THF solution (1 M, 8.5 mL, 8.5 mmol) was added at room temperature. The reaction solution was heated to 45°C and then stirred for 30 minutes. A solution of 50 nonadecan-10-one (2.0 g, 7.08 mmol) in THF (10 mL) was added dropwise and refluxed under heating for 21 hours. The reaction mixture was cooled to room temperature, then added with 45 diethyl ether and washed sequentially with water and a saturated sodium chloride solution and the organic layer was dried over anhydrous magnesium sulphate. Following filtration, the solvent was removed by distillation under reduced pressure. The residue was purified by silica gel column chromatography (cyclohexane) to obtain the titled 51 compound (1.16 g). 1H-NMR(600MHz,CDCl3)δ(ppm):0.07(s,6H),0.90(m,15H),1.21-1.41(m,28H),1.92-2.04(m,4 H),2.24(q,J=7.34Hz,2H),3.58(t,J=7.24 Hz,2H),5.09(t,J=7.15Hz,1H)
  • 92
  • [ 504-57-4 ]
  • bis(4-nonyltridecyl)5-[(1-methylpiperidine-4-carbonyl)oxy]methyl}nonanedioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 45 °C / Inert atmosphere 1.2: 21 h / Reflux 2.1: hydrogen; palladium 10% on activated carbon; acetic acid / ethyl acetate / 18 h / 20 °C 3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 4 h / 20 °C
  • 93
  • [ 504-57-4 ]
  • 4-nonyltridecan-1-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 45 °C / Inert atmosphere 1.2: 21 h / Reflux 2.1: hydrogen; palladium 10% on activated carbon; acetic acid / ethyl acetate / 18 h / 20 °C
  • 94
  • [ 504-57-4 ]
  • 9-fluorononadecan-10-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% With toluene-4-sulfonic acid; Selectfluor In dichloromethane; acetonitrile at 60℃; for 12h; Inert atmosphere;
  • 95
  • [ 504-57-4 ]
  • [ 118-00-3 ]
  • 2’,3’-O-(1-nonyldecylidene)guanosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% With hydrogenchloride; orthoformic acid triethyl ester In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; for 24h;
  • 96
  • [ 504-57-4 ]
  • nonadecan-10-yl (tert-butoxycarbonyl)-L-phenylalaninate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / tetrahydrofuran; methanol / 2 h / 0 - 25 °C 2: 1H-imidazole; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 16 h / 25 °C
  • 97
  • [ 504-57-4 ]
  • nonadecan-10-yl L-phenylalaninate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / tetrahydrofuran; methanol / 2 h / 0 - 25 °C 2: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C
  • 98
  • [ 504-57-4 ]
  • nonadecan-10-yl ((((2R,3S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-2-ethynyl-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate [ No CAS ]
  • nonadecan-10-yl ((((2R,3S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-2-ethynyl-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphoryl)-L-alaninate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 2 h / 0 - 25 °C 2.1: 1H-imidazole; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 18 h / 25 °C 3.1: trifluoroacetic acid / dichloromethane / 4 h / 25 °C 4.1: triethylamine / dichloromethane / 1 h / 20 °C / Cooling with ice; Inert atmosphere 4.2: 2.5 h / 0 - 20 °C / Inert atmosphere
  • 99
  • [ 504-57-4 ]
  • nonadecan-10-yl (tert-butoxycarbonyl)-L-alaninate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / tetrahydrofuran; methanol / 2 h / 0 - 25 °C 2: 1H-imidazole; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 18 h / 25 °C
  • 100
  • [ 504-57-4 ]
  • nonadecan-10-yl L-alaninate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / tetrahydrofuran; methanol / 2 h / 0 - 25 °C 2: 1H-imidazole; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 18 h / 25 °C 3: trifluoroacetic acid / dichloromethane / 4 h / 25 °C
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