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[ CAS No. 2985-57-1 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
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Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
3d Animation Molecule Structure of 2985-57-1
Chemical Structure| 2985-57-1
Chemical Structure| 2985-57-1
Structure of 2985-57-1 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 2985-57-1 ]

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Alternatived Products of [ 2985-57-1 ]

Product Details of [ 2985-57-1 ]

CAS No. :2985-57-1 MDL No. :MFCD10698711
Formula : C16H26O Boiling Point : -
Linear Structure Formula :- InChI Key :CGTLMVREWQIWEC-UHFFFAOYSA-N
M.W : 234.38 Pubchem ID :572479
Synonyms :

Calculated chemistry of [ 2985-57-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.62
Num. rotatable bonds : 9
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 76.69
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.56
Log Po/w (XLOGP3) : 6.64
Log Po/w (WLOGP) : 5.08
Log Po/w (MLOGP) : 4.37
Log Po/w (SILICOS-IT) : 5.13
Consensus Log Po/w : 4.96

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.14
Solubility : 0.00168 mg/ml ; 0.00000719 mol/l
Class : Moderately soluble
Log S (Ali) : -6.87
Solubility : 0.0000319 mg/ml ; 0.000000136 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -5.86
Solubility : 0.000324 mg/ml ; 0.00000138 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 1.74

Safety of [ 2985-57-1 ]

Signal Word:Danger Class:8
Precautionary Statements:P201-P202-P260-P264-P273-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P308+P313-P391-P405-P501 UN#:2430
Hazard Statements:H314-H361-H410 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2985-57-1 ]

* 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 [ 2985-57-1 ]

[ 2985-57-1 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 14353-77-6 ]
  • [ 2985-57-1 ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: 1-(4-hydroxy-phenyl)-decan-1-one With hydrazine hydrate In diethylene glycol dimethyl ether at 250℃; for 2h; Stage #2: With potassium hydroxide In diethylene glycol dimethyl ether at 190℃; for 4h; 4-Decylphenyl 2,3-dihydroxybenzoate ( B7 ) Phenol (1.83 g, 19.5 mmol) was added to decanoyl chloride (4.08 g, 21.4 mmol) , stirred at 80 until bubbles were stopped, aluminum trichloride (2.85 g, 21.4 mmol) was added, reflux was performed at 130 for 1 h. When cooled to room temperature, 1 M HCl solution was added to the mixture slowly to quench the reaction, then ethyl acetate was added for dilution, the organic phase was washed with 1 M HCl, saturated NaHCO3 and saturated NaCl successively, and dried with anhydrous Na2SO4. Rotary evaporation was conducted to remove solvent to obtain intermediate (7) as white solid .The product is not purified and characterized, and is directly used for the next step. The intermediate (7) (0.24 g, 0.96 mmol) and hydrazine hydrate (1 ml) were added to diethylene glycol (6 mL), which was stirred at 250 for 2 h and cooled to room temperature. Potassium hydroxide (0.27 g, 4.80 mmol) was added and stirred at 190 for 4 h to remove the excess hydrazine hydrate. When cooled to room temperature, water (27 mL) was added for dilution, and washed twice with ethyl acetate. The water layer was adjusted to acidic with concentrated hydrochloric acid, and extracted three times with ethyl acetate. The combined organic phase was dried with anhydrous Na2SO4 , then filtered and concentrated in vacuo, the crude material was purified by flash chromatography to afford the intermediate (8) as white solid (185 mg, 82%). 1H NMR (400 MHz, DMSO-d6): δ 9.15 (s, 1H), 6.98 (d, J = 8.0 Hz, 2H), 6.68 (d, J = 8.0 Hz, 2H), 2.47 (t, J = 7.4 Hz, 2H), 1.57-1.47 (m, 2H), 1.34-1.22 (m, 14H), 0.88 (t, J = 6.8 Hz, 3H).
71% With hydrogenchloride; mercury; zinc
With hydrogenchloride; amalgamated zinc
With hydrogenchloride; amalgamated zinc
With hydrogenchloride; mercury; zinc In ethanol
With potassium hydroxide; hydrazine hydrate 1.) diethylene glycol, reflux, 1h; 2.) reflux, 1h; Yield given. Multistep reaction;
With hydrogenchloride; mercury; zinc In ethanol Heating; Yield given;
Multi-step reaction with 2 steps 1: hydrazine hydrate / diethylene glycol / 2 h / Reflux 2: potassium hydroxide / diethylene glycol / 5 h / 20 - 200 °C

  • 2
  • [ 2985-57-1 ]
  • [ 101443-38-3 ]
YieldReaction ConditionsOperation in experiment
With nickel at 150℃; Hydrogenation;
  • 3
  • [ 50-00-0 ]
  • [ 2985-57-1 ]
  • [ 118311-80-1 ]
  • [ 118311-84-5 ]
YieldReaction ConditionsOperation in experiment
1: 10% 2: 12% With potassium hydroxide In tetralin at 150℃; for 4h;
  • 4
  • [ 67-66-3 ]
  • [ 2985-57-1 ]
  • [ 77635-20-2 ]
YieldReaction ConditionsOperation in experiment
21.8% With sodium hydroxide In methanol; water at 65℃; for 2h;
  • 5
  • [ 2493-84-7 ]
  • [ 2985-57-1 ]
  • 4-n-Decylphenyl 4'-n-octyloxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dicyclohexyl-carbodiimide for 1h; Heating;
With dmap; dicyclohexyl-carbodiimide In dichloromethane for 3h; Ambient temperature; Yield given;
  • 7
  • [ 2985-57-1 ]
  • [ 76224-59-4 ]
  • [ 160582-39-8 ]
YieldReaction ConditionsOperation in experiment
68.7% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 24h; Ambient temperature;
  • 8
  • [ 112-13-0 ]
  • [ 2985-57-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: AlCl3 / nitrobenzene / 0.5 h / 50 °C 2: Zn-Hg, 5 N HCl / ethanol / Heating
Multi-step reaction with 2 steps 1: AlCl3 / CH2Cl2 / 1.) 0 deg C, 30 min; 0 deg C, 30 min; 2.) room temperature, overnight 2: 1.) hydrazine hydrate, 2.) KOH / 1.) diethylene glycol, reflux, 1h; 2.) reflux, 1h
Multi-step reaction with 3 steps 1: AlCl3 2: N2H4+H2O; KOH; phenol / weiteres Reagens: Diaethylenglykol 3: aqueous HI; acetic acid; acetic acid anhydride
Multi-step reaction with 2 steps 1: (i), (ii) AlCl3, CS2 2: Zn-Hg, aq. HCl / ethanol
Multi-step reaction with 4 steps 1: 70 - 75 °C 2: aluminum (III) chloride / 3.5 h / 20 - 100 °C 3: hydrazine hydrate / diethylene glycol / 2 h / Reflux 4: potassium hydroxide / diethylene glycol / 5 h / 20 - 200 °C
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / 1 h / 130 °C 2.1: hydrazine hydrate / diethylene glycol dimethyl ether / 2 h / 250 °C 2.2: 4 h / 190 °C

  • 9
  • [ 2985-57-1 ]
  • [ 95206-54-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 92 percent / POCl3, KCl / 7 h / Heating 2: 88 percent / 18 h / 0 - 5 °C 3: 80 percent / LiN(iPr)2 / tetrahydrofuran / -78 °C
Multi-step reaction with 3 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight
  • 10
  • [ 2985-57-1 ]
  • [ 95206-51-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 92 percent / POCl3, KCl / 7 h / Heating 2: 88 percent / 18 h / 0 - 5 °C 3: 80 percent / LiN(iPr)2 / tetrahydrofuran / -78 °C 4: 61 percent / NaH / tetrahydrofuran / 72 h / Heating 5: 90 percent / 10percent NaOH / 4 h / Heating
Multi-step reaction with 5 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d 5: 92 percent / 10percent aq. NaOH / ethanol / Heating
  • 11
  • [ 2985-57-1 ]
  • [ 95230-40-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 92 percent / POCl3, KCl / 7 h / Heating 2: 88 percent / 18 h / 0 - 5 °C 3: 80 percent / LiN(iPr)2 / tetrahydrofuran / -78 °C 4: 61 percent / NaH / tetrahydrofuran / 72 h / Heating
Multi-step reaction with 4 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d
  • 12
  • [ 2985-57-1 ]
  • [ 95230-37-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 92 percent / POCl3, KCl / 7 h / Heating 2: 88 percent / 18 h / 0 - 5 °C 3: 80 percent / LiN(iPr)2 / tetrahydrofuran / -78 °C 4: 71 percent / NaH / tetrahydrofuran / 72 h / Heating 5: 96 percent / 10percent NaOH / 4 h / Heating
Multi-step reaction with 5 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d 5: 96 percent / 10percent aq. NaOH / ethanol / Heating
  • 13
  • [ 2985-57-1 ]
  • [ 95230-41-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 92 percent / POCl3, KCl / 7 h / Heating 2: 88 percent / 18 h / 0 - 5 °C 3: 80 percent / LiN(iPr)2 / tetrahydrofuran / -78 °C 4: 71 percent / NaH / tetrahydrofuran / 72 h / Heating
Multi-step reaction with 4 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d
  • 14
  • [ 2985-57-1 ]
  • [ 95230-38-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 92 percent / POCl3, KCl / 7 h / Heating 2: 88 percent / 18 h / 0 - 5 °C 3: 80 percent / LiN(iPr)2 / tetrahydrofuran / -78 °C 4: 61 percent / NaH / tetrahydrofuran / 72 h / Heating 5: 91 percent / 10percent NaOH / 4 h / Heating
Multi-step reaction with 5 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d 5: 91 percent / 10percent aq. NaOH / ethanol / Heating
  • 15
  • [ 2985-57-1 ]
  • [ 95230-42-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 92 percent / POCl3, KCl / 7 h / Heating 2: 88 percent / 18 h / 0 - 5 °C 3: 80 percent / LiN(iPr)2 / tetrahydrofuran / -78 °C 4: 61 percent / NaH / tetrahydrofuran / 72 h / Heating
Multi-step reaction with 4 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d
  • 16
  • [ 2985-57-1 ]
  • [ 95230-39-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 92 percent / POCl3, KCl / 7 h / Heating 2: 88 percent / 18 h / 0 - 5 °C 3: 80 percent / LiN(iPr)2 / tetrahydrofuran / -78 °C 4: 69 percent / NaH / tetrahydrofuran / 72 h / Heating 5: 89 percent / 10percent NaOH / 4 h / Heating
Multi-step reaction with 5 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d 5: 89 percent / 10percent aq. NaOH / ethanol / Heating
  • 17
  • [ 2985-57-1 ]
  • [ 95230-43-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 92 percent / POCl3, KCl / 7 h / Heating 2: 88 percent / 18 h / 0 - 5 °C 3: 80 percent / LiN(iPr)2 / tetrahydrofuran / -78 °C 4: 69 percent / NaH / tetrahydrofuran / 72 h / Heating
Multi-step reaction with 4 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d
  • 18
  • [ 334-48-5 ]
  • [ 2985-57-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 85 percent / SOCl2 2: 49 percent / AlCl3 / nitrobenzene 3: 71 percent / Zn(Hg), HCl
Multi-step reaction with 5 steps 1: thionyl chloride / 60 °C / Reflux 2: 70 - 75 °C 3: aluminum (III) chloride / 3.5 h / 20 - 100 °C 4: hydrazine hydrate / diethylene glycol / 2 h / Reflux 5: potassium hydroxide / diethylene glycol / 5 h / 20 - 200 °C
  • 19
  • [ 14353-75-4 ]
  • [ 2985-57-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 49 percent / AlCl3 / nitrobenzene 2: 71 percent / Zn(Hg), HCl
Multi-step reaction with 3 steps 1: aluminum (III) chloride / 3.5 h / 20 - 100 °C 2: hydrazine hydrate / diethylene glycol / 2 h / Reflux 3: potassium hydroxide / diethylene glycol / 5 h / 20 - 200 °C
  • 20
  • [ 2985-57-1 ]
  • [ 144381-70-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d 5: 90 percent / Me3SiBr / 1 h / 95 °C
  • 21
  • [ 2985-57-1 ]
  • [ 109954-01-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d 5: 96 percent / 10percent aq. NaOH / ethanol / Heating
  • 22
  • [ 2985-57-1 ]
  • [ 109954-02-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d
  • 23
  • [ 2985-57-1 ]
  • [ 126128-17-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) KH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d 5: 54 percent / Me3SiBr / 1 h / 95 °C
  • 24
  • [ 2985-57-1 ]
  • [5-Decyl-2-(1,4,7,10-tetraoxa-cyclotridec-11-ylmethoxy)-phenyl]-phosphonic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) KH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d 5: 66 percent / Me3SiBr / 1 h / 95 °C
  • 25
  • [ 2985-57-1 ]
  • [5-Decyl-2-(1,4,7,10-tetraoxa-cyclotetradec-12-ylmethoxy)-phenyl]-phosphonic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) KH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d 5: 49 percent / Me3SiBr / 1 h / 95 °C
  • 26
  • [ 2985-57-1 ]
  • [5-Decyl-2-(1,4,7,10-tetraoxa-cyclotetradec-11-ylmethoxy)-phenyl]-phosphonic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) KH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d 5: 71 percent / Me3SiBr / 1 h / 95 °C
  • 27
  • [ 2985-57-1 ]
  • [ 126128-21-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d 5: 97 percent / Me3SiBr / 1 h / 95 °C
  • 28
  • [ 2985-57-1 ]
  • [ 109953-99-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) KH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d 5: 93 percent / 10percent aq. NaOH / ethanol / Heating
  • 29
  • [ 2985-57-1 ]
  • [ 144381-58-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) KH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d
  • 30
  • [ 2985-57-1 ]
  • [5-Decyl-2-(1,4,7,10-tetraoxa-cyclotridec-11-ylmethoxy)-phenyl]-phosphonic acid monoethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) KH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d 5: 91 percent / 10percent aq. NaOH / ethanol / Heating
  • 31
  • [ 2985-57-1 ]
  • [5-Decyl-2-(1,4,7,10-tetraoxa-cyclotetradec-12-ylmethoxy)-phenyl]-phosphonic acid monoethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) KH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d 5: 90 percent / 10percent aq. NaOH / ethanol / Heating
  • 32
  • [ 2985-57-1 ]
  • [5-Decyl-2-(1,4,7,10-tetraoxa-cyclotetradec-11-ylmethoxy)-phenyl]-phosphonic acid monoethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) KH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d 5: 96 percent / 10percent aq. NaOH / ethanol / Heating
  • 33
  • [ 2985-57-1 ]
  • [5-Decyl-2-(1,4,7,10-tetraoxa-cyclotridec-11-ylmethoxy)-phenyl]-phosphonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) KH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d
  • 34
  • [ 2985-57-1 ]
  • [ 126128-23-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d 5: 90 percent / Me3SiBr / 1 h / 95 °C
  • 35
  • [ 2985-57-1 ]
  • [5-Decyl-2-(1,4,7,10-tetraoxa-cyclotetradec-12-ylmethoxy)-phenyl]-phosphonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) KH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d
  • 36
  • [ 2985-57-1 ]
  • [5-Decyl-2-(1,4,7,10-tetraoxa-cyclotetradec-11-ylmethoxy)-phenyl]-phosphonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) KH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d
  • 37
  • [ 2985-57-1 ]
  • [ 126128-15-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) KH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d 5: 61 percent / 10percent aq. NaOH / ethanol / Heating
  • 38
  • [ 2985-57-1 ]
  • [ 144381-62-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) KH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d
  • 39
  • [ 2985-57-1 ]
  • [ 126128-25-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d 5: 95 percent / Me3SiBr / 1 h / 95 °C
  • 40
  • [ 2985-57-1 ]
  • [5-Decyl-2-(1,4,7,10,13,16-hexaoxa-cyclononadec-17-ylmethoxy)-phenyl]-phosphonic acid monoethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d 5: 93 percent / 10percent aq. NaOH / ethanol / Heating
  • 41
  • [ 2985-57-1 ]
  • [5-Decyl-2-(1,4,7,10,13,16-hexaoxa-cyclononadec-17-ylmethoxy)-phenyl]-phosphonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d
  • 42
  • [ 2985-57-1 ]
  • [ 126128-26-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d 5: 64 percent / Me3SiBr / 1 h / 95 °C
  • 43
  • [ 2985-57-1 ]
  • [ 144381-65-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d 5: 98 percent / 10percent aq. NaOH / ethanol / Heating
  • 44
  • [ 2985-57-1 ]
  • [ 144381-64-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 92 percent / POCl3, CsCl / 7 h / Heating 2: 89 percent 3: 78 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) RT, overnight 4: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, reflux, 3 d
  • 45
  • [ 108-95-2 ]
  • [ 2985-57-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: AlCl3 / CH2Cl2 / 1.) 0 deg C, 30 min; 0 deg C, 30 min; 2.) room temperature, overnight 2: 1.) hydrazine hydrate, 2.) KOH / 1.) diethylene glycol, reflux, 1h; 2.) reflux, 1h
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / 1 h / 130 °C 2.1: hydrazine hydrate / diethylene glycol dimethyl ether / 2 h / 250 °C 2.2: 4 h / 190 °C
  • 46
  • [ 108-95-2 ]
  • [ 2985-57-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (i), (ii) AlCl3, CS2 2: Zn-Hg, aq. HCl / ethanol
  • 47
  • [ 50-00-0 ]
  • [ 2985-57-1 ]
  • [ 1162025-31-1 ]
YieldReaction ConditionsOperation in experiment
61% With oxalic acid; sodium 4-dodecylbenzenesulfonate In water at 50 - 135℃; Inert atmosphere;
  • 48
  • C16H26N2O [ No CAS ]
  • [ 2985-57-1 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In diethylene glycol at 20 - 200℃; for 5h;
  • 49
  • [ 303-38-8 ]
  • [ 2985-57-1 ]
  • 2,3-dihydroxybenzoic acid p-decyl benzyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% Stage #1: 2,3-Dihydroxybenzoic acid With dicyclohexyl-carbodiimide In acetonitrile at 50℃; for 1h; Inert atmosphere; Stage #2: 4-decylphenol With dmap In acetonitrile at 65℃; 1 Example 1: Synthesis of Compound I-1,2,3-Dihydroxybenzoic Acid to Ketophyll Ester Under N2, 2,3-dihydroxybenzoic acid (77 mg, 0.5 mmol) was dissolved in 10 ml of dry acetonitrile, N, N'-dicyclohexylcarbodiimide (155 mg, 0.75 mmol) was added, stirred at 50 ° C for 1 h,Followed by addition of 4-chlorophenol (117 mg, 0.5 mmol) and DMAP (6 mg, 0.05 mmol) at 65 C. After stirring overnight,The solvent was evaporated under reduced pressure, and 50 ml of ethyl acetate was added to the residue. The filtrate was filtered with 1 mol / L hydrochloric acid,Saturated aqueous sodium bicarbonate solution, saturated aqueous sodium chloride solution were washed three times, dried over anhydrous sodium sulfate, concentrated under reduced pressure,The residue was chromatographed on silica gel to give 100 mg of white solid in 54% yield;
52% Stage #1: 2,3-Dihydroxybenzoic acid With dicyclohexyl-carbodiimide In acetonitrile at 50℃; for 1h; Stage #2: 4-decylphenol With dmap In acetonitrile at 65℃; for 3h; General esterification procedure for the synthesis of B1-B11 and C1-C4 General procedure: N, N-dicyclohexylcarbodiimide (1.55 g, 7.5 mmol) was added to a solution of 2,3-dihydroxybenzoic acid (0.77 g, 5.0 mmol) in anhydrous CH3CN (20 mL). The reaction mixtures were stirred for 1 h at 50 oC until complete dissolution of the solids was achieved. Next corresponding phenol or alchol (5 mmol) and DMAP (0.06 g, 0.5 mmol) were added to the mixtures and stirred for 3 h at 65 oC, then the mixtures were concentrated under reduce vacuum. The residue was extracted with ethyl acetate three times and then filtered. The filtrate was washed with 5% aqueous citric acid solution, saturated NaHCO3 and brine successively. The organic phase was dried over Na2SO4, filtered, and then concentrated. The crude mixture was purified by column chromatography on silica gel to afford B1-B11 and C1-C4.
  • 50
  • [ 2985-57-1 ]
  • [ 619-66-9 ]
  • 4-(4-decylphenoxycarbonyl)benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-Carboxybenzaldehyde With thionyl chloride at 80℃; for 2h; Stage #2: 4-decylphenol With pyridine; triethylamine In dichloromethane at 50℃; for 2h;
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