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[ CAS No. 1002-84-2 ] {[proInfo.proName]}

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Chemical Structure| 1002-84-2
Chemical Structure| 1002-84-2
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Product Details of [ 1002-84-2 ]

CAS No. :1002-84-2 MDL No. :MFCD00002745
Formula : C15H30O2 Boiling Point : -
Linear Structure Formula :HO2C(CH2)13CH3 InChI Key :WQEPLUUGTLDZJY-UHFFFAOYSA-N
M.W : 242.40 Pubchem ID :13849
Synonyms :
C15:0 Fatty acid
Chemical Name :Pentadecanoic acid

Calculated chemistry of [ 1002-84-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.93
Num. rotatable bonds : 13
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 75.99
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.66
Log Po/w (XLOGP3) : 6.63
Log Po/w (WLOGP) : 5.16
Log Po/w (MLOGP) : 3.94
Log Po/w (SILICOS-IT) : 4.81
Consensus Log Po/w : 4.84

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 1.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -4.66
Solubility : 0.00528 mg/ml ; 0.0000218 mol/l
Class : Moderately soluble
Log S (Ali) : -7.21
Solubility : 0.0000148 mg/ml ; 0.000000061 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -4.91
Solubility : 0.00298 mg/ml ; 0.0000123 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 2.2

Safety of [ 1002-84-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335-H413 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1002-84-2 ]

* 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 [ 1002-84-2 ]

[ 1002-84-2 ] Synthesis Path-Downstream   1~96

  • 2
  • [ 64-17-5 ]
  • [ 1002-84-2 ]
  • [ 41114-00-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride
  • 4
  • [ 4704-94-3 ]
  • [ 1002-84-2 ]
  • [ 103389-94-2 ]
  • 5
  • [ 629-73-2 ]
  • [ 1002-84-2 ]
YieldReaction ConditionsOperation in experiment
84% With potassium permanganate; sulfuric acid; acetic acid In dichloromethane; water at 20℃; for 21h; Cooling with ice;
With diethyl ether bei der Einw. nitroser Gase;
With acetic acid bei der Einw. nitroser Gase;
With permanganate(VII) ion
With dihydrogen peroxide In water at 85℃; for 6h; Yield given;
Multi-step reaction with 2 steps 1: 20 percent / O3/O2 / 20 °C 2: 130 °C / Heating

  • 6
  • [ 1002-84-2 ]
  • [ 17746-08-6 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride
With thionyl chloride
With thionyl chloride for 8h; Heating;
With thionyl chloride for 3h; Heating;
With thionyl chloride for 1.5h; Heating;
With thionyl chloride for 1.5h; Heating / reflux; 3.A n-Pentadecanoic acid (24.3 g, 0.1 mol) was refluxed with 45 mL of thionyl chloride for 90 minutes. The thionyl chloride in excess was evaporated under reduced pressure, 20 mL of hexane was added and then evaporated under reduced pressure to remove the traces of any remaining thionyl chloride. Anhydrous aluminum chloride (13.5 g, 0.1 mol) was added to the crude pentadecanoyl chloride under stirring and external cooling. The mixture became homogeneous in about 10 minutes. Then 12 mL (0.15 mmol) of mesityl oxide was added dropwise, and the reaction mixture was stirred at room temperature for 12 h. The resulting dark viscous mass was hydrolyzed by carefully adding 50 mL of ice-cold 5% hydrochloric acid and 50 mL of diethyl ether, with external cooling (ice bath). The ethereal layer was separated and extracted another time with 20 mL of diluted hydrochloric acid, then discarded. The combined aqueous solutions. were extracted with 20 mL of diethyl ether, separated and treated with 15 mL of hexafluorophosphoric acid, when the crude pyrylium hexafluorophosphate (10, n=13) separated as a brown oil. After extraction with chloroform, separation, drying on anhydrous sodium sulfate and evaporation of the solvent, 25.9 g of crude compound were obtained. It was recrystallized twice from ethanol to afford 11.2 g (yield 25%) of pure pyrylium hexafluorophosphate (10, n=13). Characterization: m.p. 85° (determined by differential scanning calorimetry) 1H-NMR (CDCl3), δ, ppm: 7.70 (s, 1H: H-3, pyrylium), 7.61 (s, 1H: H-5, pyrylium), 3.06 (t, J=7.9 Hz, 2H: Cα-, 2.86 (s, 3H: CH3 γ-pyrylium), 2.69 (s, 3H: CH3 α-pyrylium), 1.81 (q, J=7.6 Hz, 2H: Cα-CH, 1.40 (q, J=7.6 Hz, 2H: Cα-CH2CH, 1.25 (m, 20H: 10 CH2 from fatty chain), 0.87 (t, J=6.7 Hz, 3H: CH3 from fatty chain); 13C-NMR (CDCl3), δ, ppm: 180.9 (C-6, pyrylium), 177.7 (C-4, pyrylium), 174.7 (C-2, pyrylium), 123.8 (C-3, pyrylium), 122.5 (C-5, pyrylium), 34.7 (Cα-H2-), 31.8, 29.64, 29.62, 29.60, 29.57, 29.51, 29.32, 29.30, 29.0 (2C), 27.01 (all from fatty chain), 23.5 (CH3 α-pyrylium), 22.6 (fatty chain), 21.1 (CH3 γ-pyrylium), 14.0 (CH3 from fatty chain).
With thionyl chloride; N,N-dimethyl-formamide at 20℃;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0℃; for 1h; Inert atmosphere;
With oxalyl dichloride In dichloromethane at 20℃; for 2h; Inert atmosphere;
With oxalyl dichloride In dichloromethane at 0℃; for 1h; Inert atmosphere; 1.4.1 To a solution of acid R'COOH (484 mg, 2 mmol) in dichloromethane (10 ml) placed at 0° C. under inert atmosphere of nitrogen are added three drops of dry dimethylformamide (DMF) and oxalyl chloride (1.04 ml, 12 mmol). The mixture is stirred at 0° C. for 1 h. The dichloromethane and the excess oxalyl chloride are evaporated at 70° C. under reduced pressure. The acid chloride R'COCl thus obtained is dissolved in 5 ml dichloromethane.
With thionyl chloride for 0.5h; Reflux;
With thionyl chloride at 20℃; Inert atmosphere;
With thionyl chloride for 1h; Reflux;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0℃; for 1h; Inert atmosphere;
With oxalyl dichloride In dichloromethane at 20℃;
With thionyl chloride In toluene for 4h; Reflux; The recovery standard pentadecanoic acid cholesteryl ester(hereafter referred to as 15:0-CE) was prepared accordingto Lusby et al. [20] with slight modifications. Pentadecanoicacid (121 mg, 0.5 mmol) was placed in a 50-ml flaskand dissolved in 10 ml of toluene. About 120 μl thionylchloride was added, and the solution was refluxed for 4 hto obtain the acid chloride. Afterwards, the remaining thionylchloride and parts of the toluene were removed underreduced pressure. To the residue (about 2 ml), 153 mgcholesterol (0.4 mmol) dissolved in 10 ml toluene wasadded, and the solution was stirred overnight at room temperature.The solvent was removed on a rotary evaporator,and the residue was re-dissolved in 4 ml n-hexane. Thissolution was purified by SPE. For this purpose, 15 g ofsilica gel deactivated with 20 % water (w/w) was giveninto a glass column (i.d. 2.5 cm) and pre-conditionedwith n-hexane. After 50 ml of n-hexane (fraction 1), three50-ml fractions (fractions 2-4) were collected with n-hexane/ethyl acetate (99:1, v/v) as eluent. Fractions 3 and 4yielded 154.3 and 64.8 mg of 15:0-CE. The purity inboth fractions was >99 % according to GC/MS and NMRspectroscopy analysis.
With thionyl chloride at 70℃; for 4h;
With oxalyl dichloride
With oxalyl dichloride
With thionyl chloride In tetrachloromethane for 2h; Reflux; General Procedures for Synthesis of AcidChlorides General procedure: For the preparation of chlorides higher than 10 Catoms the corresponding acid was refluxed for 2 h withthionyl chloride in CCl4.38 The solvent and the excess ofthionyl chloride were removed with the aid of the waterpump vacuum.
With thionyl chloride In N,N-dimethyl-formamide Reflux; General procedure: A solution of suitable carboxylic acids 1a-k (1.0 mmol) and DMF(0.05 ml) in thionyl chloride (1.2 mmol) were refluxed for 3.5 h. Aftercooling at room temperature the mixture was concentrated to afford theacid chlorides 2a-k. A solution of acid chlorides 2a-k (1.0 mmol) in drydistilled acetone (20 ml) was added drop wise to a suspension of potassiumthiocyanate (1.0 mmol) in dry acetone and refluxed for 1.5 hr at50 °C to afford the corresponding isothiocyanates. After cooling onroom temperature, a solution of 3-aminobenzenesulfonamide 3(1.0 mmol) in dry acetone was added in it and the reaction mixture wasrefluxed for 9 h. After completion checked by TLC (n-Hexane: Ethylacetate 1: 1) the reaction mixture was poured onto crushed ice and theresulting precipitates were collected via simple filtration, washed, driedand recrystallized from ethanol to obtain the 1-aroyl/acyl-3-(3-aminosulfonylphenyl)thioureas 4a-k in excellent yields (Scheme 1).
With thionyl chloride In 1,2-dichloro-ethane; N,N-dimethyl-formamide at 20℃; for 3h; 6; 13 Example 6: Synthesis of 1,5-anhydro-D-glucitol-2,3,4,6-O-tetrapentadecanoate Pentadecanoic acid (3 g, 12.4 mmol)The 1,2-dichloroethane (30 ml)And N, N-dimethylformamide (953 μl, 12.4 mmol) and dispersed.Add thionyl chloride (4.5 ml, 61.9 mmol),It reacted at room temperature for 3 hours. After completion of the reaction, concentrate under reduced pressure,Liquid pentadecanoyl chloride was obtained. This was used as it is in the next reaction.
With oxalyl dichloride In dichloromethane at 20℃; for 2h; Inert atmosphere; 2.2. Synthesis of NATs General procedure: NATs were synthesized by the reaction of acid chlorides with taurine. For this, long-chain fatty acids were converted to the corresponding acid chlorides by treating with 4 mol equivalents of oxalylchloride at room temperature for 2 h under nitrogen atmosphere[Kamlekar et al., 2010]. After completion of the reaction, the excessoxalyl chloride was removed under a stream of dry nitrogen gas. NATs were synthesized by the drop-wise addition of about 1 mol equivalent of the acid chloride in dichloromethane to a solution of 1.2 mol equivalent of taurine in 1 M NaOH (to maintain pH 9-10.5) underconstant stirring at room temperature. After addition of all the reagents, the reaction was allowed to continue for two hours (Scheme 1). The crude NATs obtained as slurry was dissolved in ethanol by refluxing. The solution was filtered and the filtrate was stored in freezer (ca. 4 °C) overnight. This led to precipitation of the NATs and then later recovered by filtration. The obtained NATs were further purified bycolumn chromatography on silica gel with ethyl acetate/methanol/ammonium hydroxide (80/18/2) mixture as elution solvent. The overall yield for different NATs ranged around ∼70 %. The final productswere characterized by FT-IR, 1H and 13C NMR spectroscopy as well as by LC-MS.

Reference: [1]Fierz-David; Kuster [Helvetica Chimica Acta, 1939, vol. 22, p. 89]
[2]Sethi,S.C.; Rao,B.C.S. [Indian Journal of Chemistry, 1964, vol. 2, p. 277 - 282] Trofimov,V.A. et al. [Journal of applied chemistry of the USSR, 1975, vol. 48, p. 640 - 642][Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation), 1975, vol. 48, # 3, p. 626 - 628]
[3]Roth; Blankley; Hoefle; Holmes; Roark; Trivedi; Essenburg; Kieft; Krause; Stanfield [Journal of Medicinal Chemistry, 1992, vol. 35, # 9, p. 1609 - 1617]
[4]Hoshino; Kobayashi; Ishibashi; Hashimoto [Bioscience, Biotechnology and Biochemistry, 1995, vol. 59, # 4, p. 602 - 609]
[5]Ilies, Marc Antoniu; Seitz, William A.; Johnson, Betty H.; Ezell, Edward L.; Miller, Aaron L.; Thompson, E. Brad; Balaban, Alexandru T. [Journal of Medicinal Chemistry, 2006, vol. 49, # 13, p. 3872 - 3887]
[6]Current Patent Assignee: TEXAS A&M UNIVERSITY SYSTEM - US2005/196863, 2005, A1 Location in patent: Page/Page column 30-31
[7]Location in patent: scheme or table Edmunds, Andrew J. F.; Aluja, Martin; Diaz-Fleischer, Fransico; Patrian, Bruno; Hagmann, Leonhard [Chimia, 2010, vol. 64, # 1-2, p. 37 - 42]
[8]Location in patent: experimental part Schmidt, Fanny; Douaron, Gael Le; Champy, Pierre; Amar, Majid; Seon-Meniel, Blandine; Raisman-Vozari, Rita; Figadere, Bruno [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 14, p. 5103 - 5113]
[9]Location in patent: body text Kamlekar, Ravi Kanth; Tarafdar, Pradip K.; Swamy, Musti J. [Journal of Lipid Research, 2010, vol. 51, # 1, p. 42 - 52]
[10]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE - US2011/118270, 2011, A1 Location in patent: Page/Page column 11
[11]Location in patent: experimental part Louw, Stefan; Burger, Ben V.; Le Roux, Maritha; Van Wyk, Johannes H. [Journal of Natural Products, 2011, vol. 74, # 6, p. 1364 - 1369]
[12]Location in patent: experimental part Graham, Erin R.; Tykwinski, Rik R. [Journal of Organic Chemistry, 2011, vol. 76, # 16, p. 6574 - 6583]
[13]Location in patent: scheme or table Cook, Andrew G.; Wardell, James L.; Imrie, Corrie T. [Chemistry and Physics of Lipids, 2011, vol. 164, # 2, p. 118 - 124]
[14]Bruns, Hilke; Thiel, Verena; Voget, Sonja; Patzelt, Diana; Daniel, Rolf; Wagner-Doebler, Irene; Schulz, Stefan [Chemistry and biodiversity, 2013, vol. 10, # 9, p. 1559 - 1573]
[15]Reddy, S. Thirupathi; Krovi, Krishna Prasad; Swamy, Musti J. [Crystal Growth and Design, 2014, vol. 14, # 10, p. 4944 - 4954]
[16]Hammann, Simon; Wendlinger, Christine; Vetter, Walter [Lipids, 2015, vol. 50, # 6, p. 611 - 620]
[17]Giesbertz, Pieter; Ecker, Josef; Haag, Alexander; Spanier, Britta; Daniel, Hannelore [Journal of Lipid Research, 2015, vol. 56, # 10, p. 2029 - 2039]
[18]Sivaramakrishna; Swamy, Musti J. [Journal of Chemical Sciences, 2015, vol. 127, # 9, p. 1627 - 1635]
[19]Sivaramakrishna; Swamy, Musti J. [Chemistry and Physics of Lipids, 2016, vol. 201, p. 1 - 10]
[20]Lazarević, Jelena; Kolarević, Ana; Dordević, Aleksandra; Stojanović, Gordana; Šmelcerović, Andrija; Ciuffreda, Pierangela; Santaniello, Enzo [Acta Chimica Slovenica, 2017, vol. 64, # 3, p. 603 - 612]
[21]Fattah, Tanzeela Abdul; Bua, Silvia; Saeed, Aamer; Shabir, Ghulam; Supuran, Claudiu T. [Bioorganic Chemistry, 2019, vol. 82, p. 123 - 128]
[22]Current Patent Assignee: SANNA S; NATIONAL AGRICULTURE AND FOOD RESEARCH ORGANIZATION - JP2019/89719, 2019, A Location in patent: Paragraph 0029; 0036; 0048
[23]Arul Prakash, Sukanya; Kamlekar, Ravi Kanth [Chemistry and Physics of Lipids, 2020, vol. 230]
  • 7
  • [ 1002-84-2 ]
  • [ 1562-00-1 ]
  • Pentadecanoic acid 2-sulfo-ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene
  • 8
  • [ 1002-84-2 ]
  • [ 51165-05-0 ]
  • [ 119372-42-8 ]
YieldReaction ConditionsOperation in experiment
32% With dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide 0 deg C, RT, 24 h;
  • 9
  • [ 1002-84-2 ]
  • [ 37517-78-5 ]
  • [ 112548-17-1 ]
  • 10
  • [ 1002-84-2 ]
  • [ 2386-57-4 ]
  • [ 82957-06-0 ]
  • [ 84729-49-7 ]
  • 11
  • [ 1002-84-2 ]
  • [ 84471-16-9 ]
  • [ 60951-32-8 ]
YieldReaction ConditionsOperation in experiment
51.4% In acetonitrile at 80℃; for 1h;
  • 12
  • [ 1002-84-2 ]
  • [ 19083-21-7 ]
  • [ 123894-90-6 ]
YieldReaction ConditionsOperation in experiment
87.8% With triisopropylbenzenesulfonyl chloride; trifluoroacetic acid In pyridine 1.) triisopropylbenzenesulfonyl chloride, pyridine, 70 deg. C, 5h, 2.) CF3COOH, room temperatures, 2h;
  • 13
  • [ 22521-90-0 ]
  • [ 1002-84-2 ]
  • [ 7132-64-1 ]
YieldReaction ConditionsOperation in experiment
at 130℃; Yield given. Yields of byproduct given;
at 130℃; Heating; Yield given. Yields of byproduct given;
  • 14
  • [ 89036-88-4 ]
  • [ 1002-84-2 ]
YieldReaction ConditionsOperation in experiment
78% With chromium(VI) oxide; sulfuric acid In acetone at 0℃; for 1h;
  • 15
  • [ 89861-47-2 ]
  • [ 1002-84-2 ]
  • [ 39220-65-0 ]
YieldReaction ConditionsOperation in experiment
1: 5% 2: 72% With bismuth trisphenylsulphide; dinitrogen tetraoxide In chlorobenzene at 110℃; for 12h;
  • 16
  • [ 81618-17-9 ]
  • [ 109-87-5 ]
  • [ 2765-11-9 ]
  • [ 107-31-3 ]
  • [ 1002-84-2 ]
  • [ 7132-64-1 ]
  • [ 52517-73-4 ]
YieldReaction ConditionsOperation in experiment
1: 19.6% 2: 8.8% 3: 14.1% 4: 21.3% 5: 20.3% 6: 2.2% In methanol at 90℃; for 6h; other solvents; other objects of study: energy data, velocity constant;
  • 17
  • [ 1002-84-2 ]
  • [ 629-62-9 ]
  • [ 629-76-5 ]
YieldReaction ConditionsOperation in experiment
98% With hydrogen In 1,2-dimethoxyethane at 150℃; for 16h;
  • 18
  • [ 1002-84-2 ]
  • [ 629-76-5 ]
YieldReaction ConditionsOperation in experiment
98% With hydrogen In 1,2-dimethoxyethane at 150℃; for 16h; further catalysts;
70% Stage #1: n-Pentadecanoic acid With phenylsilane; potassium-t-butoxide; C22H30ClN2RuS2(1+)*Cl(1-) In tetrahydrofuran at 60℃; for 18h; Inert atmosphere; Stage #2: With water monomer; caesium fluoride In tert-butyl methyl ether at 20℃; for 3h; Inert atmosphere; Pentadecan-1-ol (2q): To a stirred suspension of pentadecanoicacid (1q) (500 mg, 2.0627 mmol,1equiv.) in degassed THF (10 V) was added ARP-03 (21.6 mg, 0.0412 mmol, 2 mol%)and again degassed for 10 minutes. After 10 minutes of degassing, PhSiH3 (0.77mL, 6.1881 mmol, 3 equiv.) and t-BuOK (1 M in THF) (0.20 mL, 0.2062 mmol, 10mol%) were added dropwise to reaction mixture at RT. The reaction mixture washeated to 60°C and stirred for 18 h. The reaction mixture was then evaporatedto remove volatiles, then suspended in MTBE and stirred with aq. CsF solution(10%, 10 V) for 3 h. The organic layer was then separated and concentrated invacuum to furnish the crude, which was purified by column chromatography on silica gel(eluent: Ethyl acetate / n-hexane = 1/4) to afford pentadecan-1-ol (2q) (330 mg, 70%) as an off-whitesolid.1H NMR (400 MHz, DMSO- d6): δ 4.30 (t, J= 4.8 Hz, 1H), 3.40 - 3.30 (m, 2H), 1.45 - 1.10 (m, 26H), 0.84 (t, J = 6.8 Hz, 3H).13C NMR (100 MHz, DEPT -135, CDCl3): δ 63.25 (CH2), 32.96 (CH2), 32.07 (CH2), 29.83(CH2), 29.81 (CH2), 29.76 (CH2×4), 29.75 (CH2),29.58 (CH2), 29.51 (CH2), 25.89 (CH2), 22.84(CH2), 14.26 (CH3).
  • 19
  • [ 1121-30-8 ]
  • [ 1002-84-2 ]
  • [ 1026440-04-9 ]
YieldReaction ConditionsOperation in experiment
With dicyclohexyl-carbodiimide In dichloromethane for 2h; Ambient temperature;
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 2h;
  • 20
  • [ 1002-84-2 ]
  • [ 2765-11-9 ]
YieldReaction ConditionsOperation in experiment
With ThxBHO-s-Bu In tetrahydrofuran at 25℃; for 96h; Yield given;
Multi-step reaction with 2 steps 1: tetrahydrofuran / 20 °C 2: Li(Et2N)3AlH; pyridine / tetrahydrofuran / 0.5 h / 0 °C
  • 21
  • [ 1002-84-2 ]
  • [ 17278-72-7 ]
  • 13-hydroxypentadecanoic acid [ No CAS ]
  • 12-hydroxypentadecanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With E. coli cells (pCYP102, pGEc47); oxygen
With wildtype P450BM3; NADPH In phosphate buffer at 37℃; for 0.5h; Title compound not separated from byproducts;
  • 22
  • [ 1002-84-2 ]
  • (R)-2-hydroperoxypentadecanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With oxygen In dimethyl sulfoxide at 5℃; for 0.5h; Triton X-100, phosphate buffer (pH 6.0), crude enzyme from Ulva pertusa;
  • 23
  • [ 764-67-0 ]
  • [ 64-19-7 ]
  • CrO3 [ No CAS ]
  • [ 1002-84-2 ]
  • 24
  • [ 764-67-0 ]
  • [ 67-64-1 ]
  • KMnO4 [ No CAS ]
  • [ 1002-84-2 ]
  • 26
  • [ 1002-84-2 ]
  • [ 543-27-1 ]
  • C20H38O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine In N,N-dimethyl-formamide at -15℃; for 0.0833333h;
With triethylamine In acetonitrile at 4℃; for 1h; Inert atmosphere;
  • 27
  • pentadecanoic acid 3-methyl-but-2-enyl ester [ No CAS ]
  • [ 1002-84-2 ]
YieldReaction ConditionsOperation in experiment
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃;
  • 28
  • [ 1002-84-2 ]
  • 4-amino-<i>N</i>-[3-(2,3-dimethyl-phenylsulfamoyl)-phenyl]-butyramide [ No CAS ]
  • N-{3-[3-(2,3-dimethylphenylaminosulphonyl)phenylaminocarbonyl]propyl}pentadecanoic acid amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% With 4-methyl-morpholine; isobutyl chloroformate In N,N-dimethyl-formamide at -15 - 20℃;
  • 29
  • [ 1002-84-2 ]
  • pentadecanoic acid monomethoxy poly(ethylene glycol) ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With camphor sulphuric acid for 18h; Heating;
  • 30
  • [ 849150-37-4 ]
  • [ 1002-84-2 ]
  • (3-{<i>tert</i>-butoxycarbonyl-[4-(<i>tert</i>-butoxycarbonyl-{3-[<i>tert</i>-butoxycarbonyl-(3-pentadecanoylamino-propyl)-amino]-propyl}-amino)-butyl]-amino}-propyl)-(3-pentadecanoylamino-propyl)-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 10h;
  • 31
  • [ 1002-84-2 ]
  • [ 128550-06-1 ]
  • [3-(<i>tert</i>-butoxycarbonyl-{4-[<i>tert</i>-butoxycarbonyl-(3-<i>tert</i>-butoxycarbonylamino-propyl)-amino]-butyl}-amino)-propyl]-(3-pentadecanoylamino-propyl)-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 10h;
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran for 10h;
  • 32
  • [ 1002-84-2 ]
  • [ 19333-10-9 ]
  • C62H74N8O4Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: palmitic acid With potassium hydroxide In methanol for 2h; Heating; Stage #2: silicon(IV) phthalocyanine dichloride In N,N-dimethyl-formamide at 145℃; for 0.166667h; microwave irradiation;
  • 33
  • 3-n-pentadecyl-2-nitrophenol [ No CAS ]
  • O-pentadecanoyl-3-n-pentadecyl-4-nitrophenol [ No CAS ]
  • [ 1002-84-2 ]
YieldReaction ConditionsOperation in experiment
1: 55% 2: 6% With dihydrogen peroxide; methyltrioxorhenium(VII); acetic acid at 80℃; for 4h;
  • 34
  • [ 22991-47-5 ]
  • O-pentadecanoyl-3-n-pentadecyl-2-nitrophenol [ No CAS ]
  • [ 1002-84-2 ]
YieldReaction ConditionsOperation in experiment
1: 51% 2: 6% With dihydrogen peroxide; methyltrioxorhenium(VII); acetic acid at 80℃; for 4h;
  • 35
  • [ 200421-95-0 ]
  • 1-(3-hydroxy-4-nitro-phenyl)-pentadecan-1-one [ No CAS ]
  • O-pentadecanoyl-5-n-pentadecyl-2-nitrophenol [ No CAS ]
  • [ 1002-84-2 ]
  • [ 3163-07-3 ]
  • 36
  • [ 908094-01-9 ]
  • [ 1002-84-2 ]
  • [ 88785-28-8 ]
  • 13-hydroxypentadecanoic acid methyl ester [ No CAS ]
  • 12-hydroxypentadcanoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: palmitic acid With wildtype P450BM3; NADPH In phosphate buffer at 37℃; for 0.5h; Stage #2: diazomethane In diethyl ether Title compound not separated from byproducts;
  • 37
  • [ 1002-84-2 ]
  • [ 530-62-1 ]
  • [ 915203-56-4 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile
In acetonitrile Inert atmosphere; 5.1.4. General procedure for the synthesis of derivatives 5a-c. Example: diethyl 2-(1-hydroxyhexadecylidene)malonate 5b67 General procedure: Triethylamine (1.30 mL, 9.36 mmol) and magnesium chloride (0.71 g, 7.49 mmol) were added to a stirred solution of diethyl malonate (1.00 g, 6.24 mmol) in dry acetonitrile (20 mL) while cooling at 0 °C. The mixture was stirred at room temperature for 2 h. Then a previously prepared mixture of palmitic acid (1.60 g, 6.24 mmol) and N,N'-carbonyldiimidazole (1.11 g, 6.87 mmol) in dry acetonitrile (15 mL) was added, and the resulting slurry was stirred overnight. After completion (TLC monitoring, SiO2/CHCl3), the mixture was cautiously acidified with 13% HCl while keeping the temperature below 25 °C, and the resulting mixture was stirred for additional 15 min. The organic layer was separated and evaporated, and the residue was treated with ethyl acetate (20 mL). The aqueous layer was extracted with ethyl acetate (2 × 20 mL), and the organic phases were combined, washed with saturated sodium bicarbonate solution (2 × 30 mL) and brine (3 × 30 mL), dried, and concentrated to give the crude diethyl 2-(1-hydroxyhexadecylidene)malonates which was purified by column chromatography (SiO2, CHCl3) to obtain compound 5b as a white solid (mp: 32-33 °C) in a 90% yield.
  • 38
  • [ 107-85-7 ]
  • [ 1002-84-2 ]
  • pentadecanoic acid N-(3-methylbutyl)amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 48h;
  • 39
  • [ 1002-84-2 ]
  • [ 78-81-9 ]
  • pentadecanoic acid N-(2-methylpropyl)amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 48h;
  • 40
  • [ 1002-84-2 ]
  • [ 916612-13-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: acetonitrile 2.1: triethylamine; magnesium chloride / acetonitrile / 2 h / 20 °C 2.2: acetonitrile / 20 °C 2.3: 96 percent / aq. HCl / acetonitrile / 0.25 h / 20 °C 3.1: 73 percent / NaOEt; EtOH / 5 h / Heating 4.1: 83 percent / dimethylformamide / 2 h / 20 °C
  • 41
  • [ 1002-84-2 ]
  • [ 915203-40-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: acetonitrile 2.1: triethylamine; magnesium chloride / acetonitrile / 2 h / 20 °C 2.2: acetonitrile / 20 °C 2.3: 96 percent / aq. HCl / acetonitrile / 0.25 h / 20 °C 3.1: 73 percent / NaOEt; EtOH / 5 h / Heating
  • 42
  • [ 1002-84-2 ]
  • 5-bromo-3,4-dihydro-2-methylthio-6-tetradecylpyrimidin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: acetonitrile 2.1: triethylamine; magnesium chloride / acetonitrile / 2 h / 20 °C 2.2: acetonitrile / 20 °C 2.3: 96 percent / aq. HCl / acetonitrile / 0.25 h / 20 °C 3.1: 73 percent / NaOEt; EtOH / 5 h / Heating 4.1: 83 percent / dimethylformamide / 2 h / 20 °C 5.1: 77 percent / N-bromosuccinimide; benzoyl peroxide / CCl4 / 2.5 h / Heating
  • 43
  • [ 1002-84-2 ]
  • 3,4-dihydro-2-methylthio-4-oxo-6-tetradecylpyrimidin-5-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: acetonitrile 2.1: triethylamine; magnesium chloride / acetonitrile / 2 h / 20 °C 2.2: acetonitrile / 20 °C 2.3: 96 percent / aq. HCl / acetonitrile / 0.25 h / 20 °C 3.1: 73 percent / NaOEt; EtOH / 5 h / Heating 4.1: 83 percent / dimethylformamide / 2 h / 20 °C 5.1: 77 percent / N-bromosuccinimide; benzoyl peroxide / CCl4 / 2.5 h / Heating 6.1: n-BuLi / hexane; diethyl ether / 0.5 h / -70 °C 6.2: 77 percent / hexane; diethyl ether / -70 - 20 °C
  • 44
  • [ 1002-84-2 ]
  • [ 112548-17-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: acetonitrile 2.1: triethylamine; magnesium chloride / acetonitrile / 2 h / 20 °C 2.2: acetonitrile / 20 °C 2.3: 96 percent / aq. HCl / acetonitrile / 0.25 h / 20 °C
  • 45
  • [ 1002-84-2 ]
  • N1-pentadecanoyl-1,16-diamino-4,8,13-triazahexadecane tetrakis(trifluoroacetic acid) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 82 percent / EDCl / tetrahydrofuran / 10 h / 20 °C 2: 81 percent / 8 h / 20 °C
  • 46
  • [ 1002-84-2 ]
  • C23H45(2)H2NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: LiAlD4 2: HBr; H2SO4 3: Mg / tetrahydrofuran 4: Amberlyst 15
  • 47
  • [ 1002-84-2 ]
  • C23H45(2)H2NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: LiAlD4 2: HBr; H2SO4 3: Mg / tetrahydrofuran 4: Amberlyst 15
  • 48
  • [ 1002-84-2 ]
  • C26H49(2)H2NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: LiAlD4 2: HBr; H2SO4 3: Mg / tetrahydrofuran
  • 49
  • [ 1002-84-2 ]
  • [ 18787-63-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) 1,1'-carbonyldiimidazole (CDI), 2.) Et3N / 1.) THF, a) 0 deg C 3 h, b) RT, 4 h, 2.) THF, CH3CN, RT, 16 h 2: 1,4-diazabicyclo<2.2.2>octane (DABCO) / xylene / 5 h / Heating
  • 50
  • [ 1002-84-2 ]
  • N-[2,6-bis(1-methylethyl)phenyl]-3-oxo-heptadecanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) 1,1'-carbonyldiimidazole (CDI), 2.) Et3N / 1.) THF, a) 0 deg C 3 h, b) RT, 4 h, 2.) THF, CH3CN, RT, 16 h 2: 1,4-diazabicyclo<2.2.2>octane (DABCO) / xylene / 5 h / Heating 3: 1.) LDA / 1.) ether, -78 deg C, 20 min, 2.) ether, from -78 deg C to RT, 16 h
  • 51
  • [ 1002-84-2 ]
  • [ 140112-79-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2 / 8 h / Heating 2: triethylamine / tetrahydrofuran / Ambient temperature
  • 52
  • [ 1002-84-2 ]
  • Pentadecanoic acid (R)-1-[(3R,4R,5S,6R)-2-hydroxy-6-hydroxymethyl-3-((R)-3-hydroxy-tetradecanoylamino)-5-phosphonooxy-tetrahydro-pyran-4-yloxycarbonylmethyl]-dodecyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 4-(dimethylamino)pyridine (DMAP), 1-ethyl-3-(3-dimethylaminopropyl)carbodi-imide hydrochloride (WSC) / CH2Cl2 / Ambient temperature 2: boron trifluoride etherate / CH2Cl2 / 0 °C 3: H2 / Adams'platinum catalyst / ethanol
  • 54
  • [ 501940-91-6 ]
  • [ 1002-84-2 ]
  • [3-(5-{2-fluoro-4-[(5R)-2-oxo-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-3-yl]phenyl}pyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methyl pentadecanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 20℃; 38 Example 38: [3-(5-{2-Fluoro-4-[(5R)-2-oxo-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-3-yl]phenyl}pyridin-2-yl)-4,5-dihydroisoxazol-5-yl]methyl pentadecanoate (5R)-3- (3-FLUORO-4- {6- [5- (HYDROXYMETHYL)-4, 5-dihydroisoxazol-3-yl] pyridin-3-yl} phenyl)-5- (1H-1, 2, 3-TRIAZOL-1-YLMETHYL)-1, 3-oxazolidin-2-one (Example 36) (150 MG, 0.33 MMOL), pentadecanoic acid (157 mg, 0.51 MMOL), 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (131 mg, 0.69 mmol), and 4-DIMETHYLAMINOPYRIDINE (14 mg, 0.08 mmol) were added to DMF (5 ML) and allowed to stir at room temperature overnight. EtOAc (50 ml) was then added and the organic layers were washed with water (2 x 20 ml), dried over Na2SO4 and concentrated in vacuo to yield a crude residue. The residue was purified by column chromatography using 0-5% MeOH/dichloromethane to yield the product as a white solid (100 MG). MS (ELECTROSPRAV : 663.24 (MH+) FOR C36H47FN605 1H-NMR (DICHLOROMETHANE-D 8 : 0.67 (t, 3H); 1.09 (s, 21H); 1.43 (M, 3H); 2.12 (t, 2H); 3.16 (dd, 1H) ; 3.41 (dd, 1H) ; 3.81 (dd, 1H); 4.05 (m, 3H); 4.62 (t, 2H); 4.80 (M, 1H) ; 4.90 (M, 1H); 7.08 (dd, 1H); 7.34 (m, 2H); 7.54 (s, 1H); 7.64 (s, 1H); 7.73 (d, 1H) ; 7.88 (d, 1H); 8.59 (s, 1H).
  • 55
  • [ 1002-84-2 ]
  • [ 541-15-1 ]
  • (R)-(3-carboxy-2-pentadecanoyloxypropyl)trimethylammonium chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; In diethyl ether; trichloroacetic acid; REFERENCE EXAMPLE 1 After a mixture of n-pentadecanoic acid (25 g, 103 mmol) and thionyl chloride (3.15 g, 26.5 mmol) was stirred for 3 hours at 75 to 80 C., a solution of <strong>[541-15-1]L-carnitine</strong> (4.27 g, 26.5 mmol) in 25 g of trichloroacetic acid was added at 60 C. The resulting mixture was stirred for 3 hours at 80 C. under argon atmosphere and then poured into stirred 100 ml of diethyl ether. The precipitates were collected by filtration, washed with diethyl ether and then dried to give 11.8 g of a crude desired product as a colorless solid. 11.8 g of the crude product was recrystallized from isopropanol to provide 9.38 g of (R)-(3-carboxy-2-pentadecanoyloxypropyl)trimethylammonium chloride as colorless needles. m.p.: 167 to 169 C. IR (Nujol) cm-1: 3020 to 2480, 1740, 1710 NMR (DMSO-d6) delta: 0.85 (3H, t, J=6.7Hz), 1.24 (22H, br s), 1.47 to 1.57 (2H, m), 2.23 to 2.40 (2H, m), 2.62 to 2.76 (2H, m), 3.12 (9H, s), 3.68 (1H, br d), 3.81 (1H, dd, J=14, 8.1Hz), 5.42 to 5.49 (1H, m)
  • 56
  • [ 1002-84-2 ]
  • zinc(II) oxide [ No CAS ]
  • zinc(II) pentadecanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% In ethanol prepn. by refluxing ZnO with excess of carboxylic acid in EtOH for about2 h; cooled; ppt. filtered off; washed (EtOH) repeatedly; collected; kept over silica gel in vac. desiccator; elem. anal.;
  • 57
  • [ 1002-84-2 ]
  • 1,8-dihydro-6,13-di(2-hydroxybenzoyl)-dibenzo<b,i>-1,4,8,11-tetraazacyclotetradeca-4,6,11,13-tetraene [ No CAS ]
  • 7,16-bis[2-(pentadecanoyloxy)benzoyl]-5,14-dihydrodibenzo[b,i][1,4,8,11]tetraazacyclotetradecine [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With dmap; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 24h;
  • 58
  • [ 1002-84-2 ]
  • [ 56-17-7 ]
  • [ 370558-61-5 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h;
  • 59
  • [ 1002-84-2 ]
  • [ 6148-64-7 ]
  • [ 112548-17-1 ]
YieldReaction ConditionsOperation in experiment
97% Stage #1: palmitic acid With 1,1'-carbonyldiimidazole In acetonitrile Stage #2: ethyl potassium malonate With triethylamine; magnesium chloride In acetonitrile at 20℃; Stage #3: With hydrogenchloride In acetonitrile for 0.25h; Further stages.;
  • 60
  • [ 6066-82-6 ]
  • [ 1002-84-2 ]
  • [ 823780-38-7 ]
YieldReaction ConditionsOperation in experiment
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 12h;
With diisopropyl-carbodiimide In dichloromethane at 20℃; for 0.25h; Inert atmosphere;
  • 61
  • [ 1002-84-2 ]
  • C21H34NO3PolSi [ No CAS ]
  • C36H62NO4PolSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
With Diethy phosphocyanidate; triethylamine In tetrahydrofuran at 20℃; for 24h; solid phase reaction;
  • 62
  • [ 2033-24-1 ]
  • [ 1002-84-2 ]
  • 5-(1-hydroxypentadecylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% Stage #1: palmitic acid With dmap; dicyclohexyl-carbodiimide In dichloromethane Stage #2: cycl-isopropylidene malonate In dichloromethane at 20℃; for 18h;
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;
  • 63
  • [ 1002-84-2 ]
  • [ 3843-51-4 ]
YieldReaction ConditionsOperation in experiment
With Diethy phosphocyanidate; ammonia In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; for 4h;
Multi-step reaction with 2 steps 1: thionyl chloride / 0.5 h / Reflux 2: ammonia / water / Cooling with ice
  • 64
  • [ 1002-84-2 ]
  • [ 155021-56-0 ]
  • [ 1042940-02-2 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: palmitic acid With dicyclohexyl-carbodiimide In dichloromethane for 0.5h; Stage #2: tris[3-(N-tert-butoxycarbonylamino)propyl]methylamine With dmap In dichloromethane for 2h;
  • 65
  • [ 1002-84-2 ]
  • [ 1146965-80-1 ]
  • [ 1146965-81-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: palmitic acid With dicyclohexyl-carbodiimide In dichloromethane for 0.5h; Stage #2: N-[bis(4-[N',N''-bis(tert-butoxycarbonyl)guanidino]butanoyloxymethyl)methyl]-6-aminohexanamide In dichloromethane for 2h; 2.3.1.D D) Synthesis of 'Boc-protected derivatives 20a,bThe corresponding fatty acid (1.1 equiv.) and DCC (1.1 equiv.) were dissolved in DCM and stirred for 30 min. Subsequently, compound 19 (1 equiv.) was added and the resulting mixture stirred for 2 hours. The solution was filtered and the solvent removed under reduced pressure and the crude product redissolved in DCM (three times). The product was washed with H2O, extracted with DCM, dried over anhydrous MgSO4 and purified by flash chromatography using ethyl acetate/hexane mixtures to give the products as colourless oils. iV-[bis(4-[iV'^V"-bis(tert-butoxycarbonyl)guanidino]butanoyloxymethyl)methyl]-6- [iV"'-(pentadecanoyl)amino]hexanamide, 20a. LRMS (ES+) m/z 1105.7 [100, (M+Na+)].
  • 66
  • [ 1002-84-2 ]
  • [ 96-41-3 ]
  • [ 1215069-27-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: palmitic acid With dicyclohexyl-carbodiimide In dichloromethane at 40℃; for 0.5h; Stage #2: Cyclopentanol With dmap In dichloromethane at 20℃; for 24h;
  • 67
  • [ 1002-84-2 ]
  • [ 2919-23-5 ]
  • [ 1215069-29-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: palmitic acid With dicyclohexyl-carbodiimide In dichloromethane at 40℃; for 0.5h; Stage #2: cyclobutanol With dmap In dichloromethane at 20℃; for 24h;
  • 68
  • [ 1002-84-2 ]
  • [ 108-93-0 ]
  • [ 1215069-28-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: palmitic acid With dicyclohexyl-carbodiimide In dichloromethane at 40℃; for 0.5h; Stage #2: cyclohexanol With dmap In dichloromethane at 20℃; for 24h;
  • 69
  • [ 1002-84-2 ]
  • [ 1173289-99-0 ]
  • [ 1293989-40-8 ]
YieldReaction ConditionsOperation in experiment
34% Stage #1: 2-bromo-6-(4-pyridin-2-yl-piperazin-1-yl)-indeno[2,1-c]quinolin-7-one oxime With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.333333h; Inert atmosphere; Stage #2: palmitic acid In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;
  • 70
  • [ 1002-84-2 ]
  • [ 1120-36-1 ]
YieldReaction ConditionsOperation in experiment
82% With bis(triphenylphosphine)iridium(I) carbonyl chloride; acetic anhydride; potassium iodide at 160℃; for 5h; Inert atmosphere;
76% With carbon monoxide; 1,5-bis-(diphenylphosphino)pentane; acetic anhydride; potassium iodide; iron(II) chloride at 240℃; for 3h;
  • 71
  • [ 1002-84-2 ]
  • [ 102522-47-4 ]
  • N-[tris(tert-butyldimethylsilyloxymethyl)methyl]pentadecamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: palmitic acid With dicyclohexyl-carbodiimide In dichloromethane for 0.5h; Stage #2: 6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecan-6-amine With dmap In dichloromethane for 2h;
  • 72
  • [ 1002-84-2 ]
  • [ 88988-71-0 ]
  • [ 1346876-47-8 ]
YieldReaction ConditionsOperation in experiment
69% With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere; Three grams of 4 (7.4 mmol), 2.7 g pentadecanoic acid (11.1 mmol), 0.17 g DMAP (1.48 mmol), 150 mL DCM and 3.1 g DCC (14.8 mmol) were added to a flame-dried, N2 protected 250 mL flask. The reaction was cooled to 0 °C for 15 min and allowed to stand at room temperature for 24 h. The reaction was stopped by adding 5 mL acetic acid and stirred for 0.5 h. The sample was stored at a -20 °C overnight and the resulting precipitate removed by filtering. The solvent was evaporated and the resulting residues were dissolved in EtOAC, washed with 1 M HCl (30 mL × 3), satd NaHCO3 (30 mL × 3), brine (30 mL × 3) and dried over Na2SO4. The intermediate 5 was purified using column chromatography using petroleum ether/DCM (1:4) as a mobile phase. Product yield was 69%. 1-O-Hexadecyl-2-pentadenoyl-3-O-benzyl-glycerol (5) has a Rf 0.25 (petroleum ether/DCM 1:4), a 631.3 m/z (MW = 630.5) by ESI-MS and 1H NMR (400 MHz, CDCl3): ς 7.33 (m, 5H, Ph), ς 5.18 (quintet, 1H, CH), ς 4.54-4.56 (AB, 2H, CH2Ph), ς 3.63 (d, 2H, CH2CHCH2), ς 3.58 (d, 2H, CH2CHCH2), ς 3.42 (m, 2H, OCH2C15H31), ς 2.34 (t, 2H, CH2COO), ς 1.62 (quintet, 2H, β-CH2), ς 1.53 (quintet, 2H, β-CH2), ς 1.26 (br s, 48H, 24 × CH2), ς 0.887 (t, 6H, CH3 × 2), and ESI-MS+ of 631.3 m/z (MW = 630.5).
  • 73
  • [ 1002-84-2 ]
  • [ 111-27-3 ]
  • [ 42218-22-4 ]
YieldReaction ConditionsOperation in experiment
90% With silphos at 20℃; for 0.0833333h; Neat (no solvent);
  • 74
  • 4′-methoxybenzyl hexadecanoate [ No CAS ]
  • [ 1002-84-2 ]
YieldReaction ConditionsOperation in experiment
99% With silver hexafluoroantimonate; 1,2,3-trimethoxybenzene In dichloromethane at 40℃; for 8h;
  • 75
  • [ 1002-84-2 ]
  • [ 824-94-2 ]
  • 4′-methoxybenzyl hexadecanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With diisopropylamine; sodium iodide In 1-methyl-pyrrolidin-2-one at 80℃; for 1h;
  • 76
  • [ 35599-77-0 ]
  • [ 1002-84-2 ]
  • [ 79243-24-6 ]
YieldReaction ConditionsOperation in experiment
45% Stage #1: palmitic acid With sodium hydride; lithium diisopropyl amide In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 1-iodotridecane In tetrahydrofuran; mineral oil at 45℃; for 6h; Inert atmosphere;
  • 77
  • [ 1002-84-2 ]
  • (2,3-dihydrothieno[3,4-b][1,4]oxathiin-2-yl)methanol [ No CAS ]
  • (2,3-dihydrothieno[3,4-b][1,4]oxathiin-2-yl)methyl pentadecanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% Stage #1: palmitic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.5h; Stage #2: (2,3-dihydrothieno[3,4-b][1,4]oxathiin-2-yl)methanol In dichloromethane at 50℃; for 24h;
  • 78
  • [ 1002-84-2 ]
  • [ 302-27-2 ]
  • 14-O-debenzoylaconitine [ No CAS ]
  • C49H75NO12 [ No CAS ]
  • [ 466-24-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium chloride In water
  • 79
  • [ 1002-84-2 ]
  • [ 2065-37-4 ]
  • [ 1504583-92-9 ]
  • 80
  • [ 1002-84-2 ]
  • [ 2065-37-4 ]
  • [ 76309-63-2 ]
  • 81
  • [ 1002-84-2 ]
  • C43H78N6O18 [ No CAS ]
  • C58H106N6O19 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide 3.2 NHBoc-protected 5b Pentadecanoic acid 99% (40 mg, 0.17 mmol), DIEA (82 μ, 0.49 mmol), dry DMF (2 mL), HBTU (75 mg, 0.20 mmol), If (80 mg, 0.08 mmol). Purification by flash column chromatography (Si02, EtOAc:petroleum ether) gave the corresponding NHBoc-protected 5b as a white solid (77 mg, 78%).lU NMR (400 MHz, CD3OD) δ 5.13 (br s, 1H, H-l '), 5.04 (br d, J = 3.6 Hz, 1H, H-l "), 4.03 (m, 1H, H-5"), 3.67-3.30 (m, 14H, H-l , H-3, H-4, H-5, H-6, H-2', H-4', H-5', H-6' (2H), H-2", H-3", H-6" (2H)), 3.16 (t, J = 9.9 Hz, 1 H, H- 4"), 2.21 (t, J = 7.8 Hz, 2H, NHCOCH2(CH2)i2CH3), 2.13-1.98 (m, 2H, H-2eq, H-3'eq), 1.66 (app. q, J = 12.2 Hz, 1H, H-3'ax), 1.62- 1.28 (m, 70H, H-2ax, 5xC02C(CH3)3, NHCOCH2(CH2)i2CH3), 0.90 (t, J = 7.0 Hz, 3H, NHCOCH2(CH2)i2CH3);13C NMR (100 MHz, CD3OD) δ 177.0 (NHCO), 159.3, 159.2, 158.0, 157.8, 157.6, 99.9 (anomeric C), 99.4 (anomeric C), 83.2, 82.7, 80.7, 80.5, 80.4, 80.2, 77.0, 73.5, 72.7, 72.1 , 70.7, 66.6, 57.0, 51.8, 51.1 , 42.0, 41.6, 37.1 , 35.9, 34.3, 33.1, 31.8, 30.8, 30.7, 30.5, 28.9, 28.83, 28.81 , 27.0, 23.7, 14.4; LR-ESI m/z calc'd for CssHioeNeOig 1 190.75, found 1191.83 [M+H]+.
  • 82
  • [ 1002-84-2 ]
  • [ 1376134-24-5 ]
  • C33H43NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 0.583333h; Sealed tube;
With potassium carbonate In N,N-dimethyl-formamide; acetonitrile at 90℃; for 0.583333h; Derivatization of fatty acids: General procedure: 150 μL standard fatty acid mixtures, 200 μL BCETS and 100 μL DMF were added orderly to a 2 mL vial containing 15 mg K2CO3. The vial was sealed and allowed to react in a water bath at 90 °C for 35 min. 100μL supernatant obtained above was removed to dry under a stream of nitrogen gas in a 2 mL vial and then 15 mg K2CO3, 200 μL BCETS and 100 μL DMF were added orderly into the vial. The vial was sealed and allowed to react in a water bath at 90 °C for 35 min. After the reaction was completed, the mixture was cooled to room temperature. The derivatization solution was syringe filtered using a 0.22 mm nylon filter and injected directly into the chromatograph column. The injected volume was 10 μL. The derivatization procedure of fatty acids with BCETS was shown in Fig. 2.
  • 83
  • myricyl pentadecanoate [ No CAS ]
  • [ 593-50-0 ]
  • [ 1002-84-2 ]
YieldReaction ConditionsOperation in experiment
1: 1.5 mg 2: 1.3 mg With potassium hydroxide In methanol for 2h; Inert atmosphere; Reflux; Saponification of 3 Compound 3 (6mg) was refluxed with 1N methanolic KOH (10mL) under N2 atmosphere for 2h. After reflux, the mixture was concentrated, diluted with water and extracted with CHCl3. The CHCl3 extract was concentrated and column chromatographed over silica gel to get myricyl alcohol (1.5mg), CH3(CH2)29-OH, mp 89°C (lit. 88°C, Weast, 1976) and pentadecanoic acid (1.3mg), mp 53°C (lit. 53-54°C, Weast, 1976).
  • 84
  • [ 1002-84-2 ]
  • C26H31NO7 [ No CAS ]
  • C41H59NO8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; 4. General procedurefor the synthesisof compounds IIa-n and IIIa-i,l-n. General procedure: A mixture of the corresponding acids (0.16 mmol), 4-dimethylaminopyridine (DMAP, 0.02 mmol), diisopropylcarbodiimide (DIC, 0.16 mmol), and 3 or 4 (0.1 mmol) in dry dichloromethane(10 mL) was stirred at room temperature. When the reaction was complete according to TLC analysis, the mixture was diluted by dichloromethane (30 mL), washed by aq. HCl (0.1 M, 20 mL), 5 % aq. NaHCO3 (20 mL) and brine (20 mL), dried over anhydrous Na2SO4, concentrated in vacuo, and purified by PTLC to give the pure target products IIa-n and IIIa-i,l-n.
  • 85
  • [ 1002-84-2 ]
  • C27H33NO7 [ No CAS ]
  • C42H61NO8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; 4. General procedurefor the synthesisof compounds IIa-n and IIIa-i,l-n. General procedure: A mixture of the corresponding acids (0.16 mmol), 4-dimethylaminopyridine (DMAP, 0.02 mmol), diisopropylcarbodiimide (DIC, 0.16 mmol), and 3 or 4 (0.1 mmol) in dry dichloromethane(10 mL) was stirred at room temperature. When the reaction was complete according to TLC analysis, the mixture was diluted by dichloromethane (30 mL), washed by aq. HCl (0.1 M, 20 mL), 5 % aq. NaHCO3 (20 mL) and brine (20 mL), dried over anhydrous Na2SO4, concentrated in vacuo, and purified by PTLC to give the pure target products IIa-n and IIIa-i,l-n.
  • 86
  • [ 1002-84-2 ]
  • [ 26687-82-1 ]
  • arctigenin pentadecanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In chloroform; at 20℃; for 6h; Into 10 mL of chloroform were dissolved 75 mg (0.2 mmol) of <strong>[26687-82-1]arctigenin</strong> and 48.5 mg (0.2 mmol) of pentadecanoic acid. Thereto were added 76.68 mg (0.4 mmol) of the water-soluble carbodiimide and 48 mg (0.4 mmol) of DMAP. In chloroform, the reactive components were caused to react with each other at room temperature for 6 hours. Water was added to the reaction liquid, and this system was stirred. The resultant organic layer was then washed with 1 N HCl, and a saturated solution of NaHCO3 in water. The chloroform layer was distilled off under a reduced pressure to yield <strong>[26687-82-1]arctigenin</strong> pentadecanoate.
  • 87
  • [ 941-69-5 ]
  • [ 1002-84-2 ]
  • [ 1121-31-9 ]
  • C29H40N2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With tetraethylene glycol monododecyl ether; dicyclohexyl-carbodiimide In water for 0.333333h; Sonication; Cooling with ice;
  • 88
  • [ 2437-56-1 ]
  • [ 124-38-9 ]
  • [ 1002-84-2 ]
YieldReaction ConditionsOperation in experiment
51% Stage #1: 1-tridecene With bis(cyclopentadienyl)titanium dichloride; isopropylmagnesium chloride In diethyl ether at 30℃; for 8h; Schlenk technique; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran at 20℃; for 0.5h; Schlenk technique; Inert atmosphere; regioselective reaction;
  • 89
  • [ 1002-84-2 ]
  • [ 109-55-7 ]
  • N-pentadecanamidopropyl-N,N-dimethylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With aluminum oxide; sodium fluoride In neat (no solvent) at 160℃; for 11h; Inert atmosphere; Synthesis of 1a Product General procedure: A 250-mL two-necked flask fixed with a reflux condenserwas charged with pentadecanoic acid (5.00 g, 20.63 mmol),3-(dimethylamino)-1-propylamine (4.22 g, 41.25 mmol),NaF (0.09 g, 2.06 mmol). The temperature of the reactionwas raised to 160° C for 6 h under an argon atmosphere andthe generated byproduct H2O was continuously absorbedusing a bent distilling adapter, connected with a reflux condenserand filled with Al2O3, throughout the course of thereaction. Then a further 3.16 g (30.94 mmol) of3-(dimethylamino)-1-propylamine was introduced into theflask and the reaction refluxed for a further 5 h. Afterremoving the leftover 3-(dimethylamino)-1-propylamine,the residue was washed with cold acetone: water(93:7 mL 9 3) followed by vacuum drying to obtain compound1a as a white solid. Compounds (1b and 1c) of this series were synthesizedusing the same method adopted for the compound 1a. N-pentadecanamidopropyl-N,N-dimethylamine (1a):White solid (5.91 g, 88 % yield). 1H NMR (500 MHz,CDCl3) δ (ppm): 0.84 (t, J = 6.71 Hz, 3H), 1.18-1.28 (m,22H), 1.50-1.59 (m, 2H), 1.59-1.68 (m, 2H), 2.10 (t,J = 7.32 Hz, 2H), 2.21 (s, 6H), 2.36 (t, J = 6.41 Hz, 2H),3.24-3.33 (m, 2H), 6.93 (br S, 1H (NH).
  • 90
  • [ 1002-84-2 ]
  • [ 62-31-7 ]
  • [ 1447947-45-6 ]
YieldReaction ConditionsOperation in experiment
53.3% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane; ethyl acetate at 0 - 20℃; for 0.5h; Inert atmosphere; General procedure: Dopamine hydrochloride (60.7 mg, 0.32 mmol) and palmitoleic acid (91.0 µL, 0.32 mmol) were mixed in dry CH2Cl2(1 mL) under an Ar atmosphere, and triethylamine (133 µL, 0.96 mmol) was added at 0°C. PPACA (50% in ethyl acetate, 200 µL, 0.32 mmol) was slowly added over 30 min at the same temperature, and the reaction mixture was stirred at room temperature overnight. The mixture was worked up followed by evaporation, and the residue was purified by column chromatography (eluent; EtOAc-hexane=1 : 1-4 : 1) to give N-palmitoleoyl dopamine (22.6 mg, 18.1%) as a colorless oil.
  • 91
  • [ 1002-84-2 ]
  • C15H(2)H29O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% Stage #1: palmitic acid With d8-isopropanol; 10% Pt/activated carbon; water-d2 at 120℃; for 24h; Stage #2: With water; sodium hydroxide at 70℃; for 24h;
  • 92
  • [ 1002-84-2 ]
  • [ 92-88-6 ]
  • C27H38O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: palmitic acid; 4,4'-Dihydroxybiphenyl With dmap In tetrahydrofuran for 0.0833333h; Stage #2: With diisopropyl-carbodiimide In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; General procedure: To a stirred solution of 1.86 g (10 mmol) of 4,4-dihydroxybiphenyl (biphenol) in 10 ml THF, 50 mg (0.4 mmol) of DMAP and 10 mmol of carboxylic acid were added. After the mixture was stirred for 5 min, 1.26 g (10 mmol) of DIC was added into the mixture, and then, the final reaction mixture was stirred under nitrogen purge for 3 h at room temperature through Steglich esterification. Insoluble solids, primarily precipitated urea, were then filtered off, and the filtrate was concentrated by a rotary evaporator until complete solvent removal. The residue was dissolved in a small amount of CHCl3 and purified by a silicagel column, using CHCl3 as an eluent to remove residual reactants and side reaction compounds.
  • 93
  • [ 1002-84-2 ]
  • [ 38076-46-9 ]
YieldReaction ConditionsOperation in experiment
With ammonium sulfate; dipotassium hydrogenphosphate; potassium dihydrogenphosphate; D-glucose; Ktedonobacter racemifer 9955; sodium citrate; magnesium sulfate In ethylene glycol; dimethyl sulfoxide at 30℃; for 16h;
  • 94
  • [ 1002-84-2 ]
  • 2-(4-aminopiperidine-1-carbonyl)-4-ethyl-2H-benzo[b][1,4]thiazin-3(4H)-one [ No CAS ]
  • N-(1-(4-ethyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]thiazine-2-carbonyl)piperidin-4-yl)-pentadecanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; 4.1.12 General procedure for the preparation of 19a-19g, 20a-20h, 21a-21f, and 22 General procedure: A solution of compound 9, 12, or 15 (0.3mmol), acids 18a-18g (0.33mmol), HBTU (0.35mmol), DIPEA (1.5mmol) in dichloromethane (20mL) was stirred at room temperature for 2h. The reaction mixture was diluted with dichloromethane, and washed sequentially with water, 1mol/L HCl, saturated aqueous sodium bicarbonate and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography (hexanes: EtOAc=1: 1) to obtain compound 19a-19g, 20a-20h, 21a-21f, or 22 (yield 20%-87%).
  • 95
  • [ 1002-84-2 ]
  • 4-ethyl-3-oxo-N-(piperidin-4-yl)-3,4-dihydro-2H-benzo[b][1,4]thiazine-2-carboxamide [ No CAS ]
  • 4-ethyl-3-oxo-N-(1-pentadecanoylpiperidin-4-yl)-3,4-dihydro-2H-benzo[b][1,4]thiazine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; 4.1.12 General procedure for the preparation of 19a-19g, 20a-20h, 21a-21f, and 22 General procedure: A solution of compound 9, 12, or 15 (0.3mmol), acids 18a-18g (0.33mmol), HBTU (0.35mmol), DIPEA (1.5mmol) in dichloromethane (20mL) was stirred at room temperature for 2h. The reaction mixture was diluted with dichloromethane, and washed sequentially with water, 1mol/L HCl, saturated aqueous sodium bicarbonate and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography (hexanes: EtOAc=1: 1) to obtain compound 19a-19g, 20a-20h, 21a-21f, or 22 (yield 20%-87%).
  • 96
  • [ 106-02-5 ]
  • [ 1002-84-2 ]
YieldReaction ConditionsOperation in experiment
71% With palladium 10% on activated carbon; W(OTf)<SUB>6</SUB>; hydrogen at 135℃; for 12h; 31 Preparation of N-Pentadecanoic acid by Pentadecanolide General procedure: Specific methods are as follows: propiolactone was added (0.36g, 5mmol), palladium on carbon (10%, 26.5mg, 0.025mmol, 0.5mol%) in the reactor and W (OTf)6(107.8mg, 0.1mmol, 2mol%). A hydrogen balloon connected to the top of the reactor, and the reactor was purged with hydrogen gas atmosphere. Hydrogen atmosphere at normal pressure, the reaction was stirred at 135 deg.] C after 12h, detected by gas, γ- valerolactone complete conversion of starting material, and only n-valeric acid. The method carried out as follows completion of the hydrogenation reaction of the ring-opening reaction system separation, to obtain the desired product n-valeric acid: The reaction was completed reaction mixture was dissolved with methylene chloride, filtered to remove the palladium on carbon catalyst and W (OTf)699% yield measured propionic acid, purity of the product was 99%. NMR data for the product using the embodiment of the present invention is the NMR identified the product as follows:The specific reaction procedure and the operation method were the same as in Example 27, and the yield was 71%, and the purity of the product was 99%. The product was subjected to nuclear magnetic identification using the manner described in the present invention, and the NMR data of the product were as follows:
71% With palladium on activated carbon; W(OTf)<SUB>6</SUB>; hydrogen In neat (no solvent) at 135℃; for 12h;
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