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[ CAS No. 24767-82-6 ] {[proInfo.proName]}

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Chemical Structure| 24767-82-6
Chemical Structure| 24767-82-6
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Product Details of [ 24767-82-6 ]

CAS No. :24767-82-6 MDL No. :MFCD00059442
Formula : C14H22O3S Boiling Point : -
Linear Structure Formula :- InChI Key :BQPVBPLMUCJNOX-UHFFFAOYSA-N
M.W : 270.39 Pubchem ID :599295
Synonyms :

Calculated chemistry of [ 24767-82-6 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.57
Num. rotatable bonds : 8
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 74.43
TPSA : 51.75 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.4
Log Po/w (XLOGP3) : 4.32
Log Po/w (WLOGP) : 4.75
Log Po/w (MLOGP) : 3.51
Log Po/w (SILICOS-IT) : 3.37
Consensus Log Po/w : 3.87

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.96
Solubility : 0.0299 mg/ml ; 0.00011 mol/l
Class : Soluble
Log S (Ali) : -5.12
Solubility : 0.00205 mg/ml ; 0.00000757 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.27
Solubility : 0.00147 mg/ml ; 0.00000542 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.89

Safety of [ 24767-82-6 ]

Signal Word:Warning Class:
Precautionary Statements:P210-P264-P270-P280-P301+P312-P330-P370+P378-P403+P235-P501 UN#:
Hazard Statements:H302-H227 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 24767-82-6 ]

* 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 [ 24767-82-6 ]

[ 24767-82-6 ] Synthesis Path-Downstream   1~70

  • 1
  • [ 24767-82-6 ]
  • [ 661-11-0 ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; ethylene glycol
With potassium fluoride; diethylene glycol
  • 2
  • [ 908094-01-9 ]
  • [ 24767-82-6 ]
  • [ 34643-97-5 ]
  • [ 34643-98-6 ]
YieldReaction ConditionsOperation in experiment
Multistep reaction;
  • 3
  • [ 2346-00-1 ]
  • [ 24767-82-6 ]
  • [ 7128-87-2 ]
  • 4
  • [ 111-70-6 ]
  • [ 98-59-9 ]
  • [ 24767-82-6 ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate; 1-hexadecyl-1H-imidazole In water at 25℃; for 4h;
89% With dmap; triethylamine In dichloromethane at 0 - 20℃; for 5h;
88% With pyridine at 0℃; for 3h;
86% With dmap; triethylamine In dichloromethane at 20℃;
85.2% With pyridine for 4h; <0 deg C;
76.4% With pyridine at 0 - 5℃; for 16h;
73% Stage #1: n-heptan1ol With potassium hydroxide In dichloromethane at 0℃; for 0.5h; Stage #2: p-toluenesulfonyl chloride In dichloromethane at 0 - 20℃; for 6h;
72% With pyridine In dichloromethane at 0 - 20℃; for 45h; Inert atmosphere;
With pyridine
With pyridine at 0℃; for 24h; Yield given;
With pyridine at 0℃;
With pyridine at 10 - 20℃; for 3h; 4.2.1. General procedure for preparation of alkyl 4-methylbenzenesulphonates General procedure: 4-Methylbenzenesulphonyl chloride (55 mmol) was added slowly to a mixture of a primary alcohol (50 mmol) and 20 ml of pyridine at 10 °C. The reaction mixture was stirred for 3 h at 20 °C. After that 120 ml of 25 % hydrochloric acid was slowly added. The reaction mixture was then extracted with chloroform, organic layer dried with Na2SO4 and evaporated to yield alkyl 4-methylbenzenesulphonate as colourless oily liquid or white solid, which was used without further purification. Ethyl 4-methylbenzenesulphonate was purchased from Fluka.
With sodium hydroxide In tetrahydrofuran at 0 - 40℃; for 4h; 1.1.1 Example 1: 1. Put heptanol (141mL, 1.0mol),P-toluenesulfonyl chloride (210g, 1.5mol),Tetrahydrofuran (850ml) is mixed in a 2 liter reaction flask,Cool down to 0 in ice water bath,Slowly add NaOH (168g, 3.0mol) under mechanical stirring,Move the reaction flask to an oil bath at 40°C,Continue to stir for about 4 hours and stop the reaction.Distill the tetrahydrofuran in the system from the system,Then a milky white (with very light yellow) solid was obtained.

Reference: [1]Asano, Keisuke; Matsubara, Seijiro [Organic Letters, 2009, vol. 11, # 8, p. 1757 - 1759]
[2]Erdeljac, Nathalie; Bussmann, Kathrin; Schöler, Andrea; Hansen, Finn K.; Gilmour, Ryan [ACS Medicinal Chemistry Letters, 2019, vol. 10, # 9, p. 1336 - 1340]
[3]Burns, Dennis H.; Miller, Jeffrey D.; Chan, Ho-Kit; Delaney, Michael O. [Journal of the American Chemical Society, 1997, vol. 119, # 9, p. 2125 - 2133]
[4]Erdeljac, Nathalie; Kehr, Gerald; Ahlqvist, Marie; Knerr, Laurent; Gilmour, Ryan [Chemical Communications, 2018, vol. 54, # 85, p. 12002 - 12005]
[5]Badr, M. Z. A.; El-Naggar, G. M.; Aly, M. M.; Fahmy, A. M. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 11, p. 961 - 964]
[6]Biagi; Giorgi; Livi; Scartoni; Lucacchini [Il Farmaco, 1992, vol. 47, # 12, p. 1457 - 1476]
[7]Chu, Yen-Ho; Hwang, Chun-Chieh; Chen, Chien-Yuan; Tseng, Min-Jen [Chemical Communications, 2020, vol. 56, # 79, p. 11855 - 11858]
[8]Naganna, Nimmashetti; Madhavan, Nandita [Organic Letters, 2013, vol. 15, # 22, p. 5870 - 5873]
[9]Jacobs,T.L.; Macomber,R.S. [Journal of the American Chemical Society, 1969, vol. 91, # 17, p. 4824 - 4837]
[10]Amarilio, David S.; Varveri, Fannie S. [Monatshefte fur Chemie, 1991, vol. 122, # 3, p. 139 - 144]
[11]Cheng, P.; Blumstein, A.; Subramanyam, S. [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1995, vol. 269, p. 1 - 38]
[12]Timko, Lukáš; Fischer-Fodor, Eva; Garajová, Mária; Mrva, Martin; Chereches, Gabriela; Ondriska, František; Bukovský, Marián; Lukáč, Miloš; Karlovská, Janka; Kubincová, Janka; Devínsky, Ferdinand [European Journal of Medicinal Chemistry, 2015, vol. 93, p. 263 - 273]
[13]Current Patent Assignee: GUANGQI JUNHONG XIAMEN TECH SERVICE - CN113292401, 2021, A Location in patent: Paragraph 0030-0032
  • 5
  • [ 24767-82-6 ]
  • [ 4733-50-0 ]
  • [ 75941-34-3 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide 1.) water, reflux, 7 h; 2.) toluene, reflux; Multistep reaction;
  • 6
  • [ 24767-82-6 ]
  • [ 592-76-7 ]
YieldReaction ConditionsOperation in experiment
With 18-crown-6 ether; potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol at 25.4℃;
  • 7
  • [ 24767-82-6 ]
  • [ 44961-22-0 ]
YieldReaction ConditionsOperation in experiment
80% With sodium azide In N,N-dimethyl-formamide at 80℃; for 12h;
With sodium azide In N,N-dimethyl-formamide at 80℃; for 5h; Inert atmosphere;
  • 8
  • [ 24767-82-6 ]
  • [ 2307-00-8 ]
  • [ 39519-89-6 ]
  • [ 134276-60-1 ]
  • 9
  • [ 24767-82-6 ]
  • [ 116223-48-4 ]
  • trans-1-(4-Heptyloxyphenyl)-2-(4-heptylpyridinium-p-toluenesulfonate)ethylene [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% In acetonitrile at 50℃; for 24h;
  • 10
  • [ 24767-82-6 ]
  • [ 13362-78-2 ]
  • trans-1,2-Bis(4-heptylpyridinium-p-toluenesulfonate)ethylene [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile at 50℃; for 24h;
  • 11
  • [ 24767-82-6 ]
  • [ 108-86-1 ]
  • [ 1078-71-3 ]
YieldReaction ConditionsOperation in experiment
With CuBr*Me2S-LiBr; lithium thiophenoxide; magnesium 1) THF, reflux; 2) THF, HMPA, rt, 24 h; further reagents and conditions; Yield given. Multistep reaction;
  • 12
  • [ 24767-82-6 ]
  • [ 75-29-6 ]
  • [ 124-18-5 ]
  • [ 871-83-0 ]
  • [ 112-95-8 ]
YieldReaction ConditionsOperation in experiment
With CuBr*Me2S-LiBr; lithium thiophenoxide; magnesium 1) THF, reflux, 2 h; 2) THF, HMPA, 67 deg C, 24 h; further reagents; Yield given. Multistep reaction;
  • 13
  • [ 24767-82-6 ]
  • [ 578-57-4 ]
  • [ 104941-42-6 ]
YieldReaction ConditionsOperation in experiment
With CuBr*Me2S-LiBr; lithium thiophenoxide; magnesium 1) THF, reflux, 3-4 h; 2) THF, HMPA, rt, 24 h; further reagents and conditions; Yield given. Multistep reaction;
  • 14
  • [ 24767-82-6 ]
  • [ 677-22-5 ]
  • [ 124-18-5 ]
  • [ 112-95-8 ]
  • [ 17302-14-6 ]
YieldReaction ConditionsOperation in experiment
50% With CuBr*Me2S-LiBr; lithium thiophenoxide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at 67℃; for 24h; further reagents;
  • 15
  • [ 24767-82-6 ]
  • [ 111-71-7 ]
YieldReaction ConditionsOperation in experiment
85% With oxygen In hexane for 1h; Heating;
YieldReaction ConditionsOperation in experiment
Rk. m. Eg. sowie m. Eg. u. Natriumacetat;
Rk. mit 4-(3,5-Dimethoxyphenyl)but-1-in(11), Li-Salz -> (12);
fuer d. Ionisierung;
Rk. mit HMPT*HCl -> n-Heptylchlorid u. HMPT-toluolsulfonsaeure;
Rk. mit LiCl/HMPT -> n-Heptylchlorid u. HMPT-toluolsulfonsaeure;
Acetolyse: Geschw.-konst. k(t); ΔH(excit.), ΔS(excit.), ΔE(excit.);
Rk. mit (CH3)3COK (Kinetik): Geschw.-Konst.;

YieldReaction ConditionsOperation in experiment
In acetic acid at 65 - 100℃;
YieldReaction ConditionsOperation in experiment
p-TsCl, Heptanol in Ae./KOH;
Toluol-sulfonylchlorid-(4), Natriumheptylat;
Tosylchlorid, n-Heptanol/HMPT;
Hepten-1-ol, p-Tolylsulfonylchlorid;
Examples of the sulfonic acid ester of the formula (V') include the following: ... isopropyl p-toluenesulfonate, butyl p-toluenesulfonate, pentyl p-toluenesulfonate, hexyl p-toluenesulfonate, heptyl p-toluenesulfonate, octyl p-toluenesulfonate, nonyl p-toluenesulfonate, and decyl p-toluenesulfonate; ...

  • 19
  • [ 24767-82-6 ]
  • [ 91-20-3 ]
  • 4-α-naphthylheptane [ No CAS ]
  • 4-β-naphthylheptane [ No CAS ]
YieldReaction ConditionsOperation in experiment
at 180℃; for 5h;
  • 20
  • [ 24767-82-6 ]
  • [ 91-20-3 ]
  • [ 2876-45-1 ]
  • [ 2876-52-0 ]
  • 2-β-naphthylheptane [ No CAS ]
  • 2-α-naphthylheptane [ No CAS ]
  • [ 131881-18-0 ]
  • [ 131881-19-1 ]
YieldReaction ConditionsOperation in experiment
at 180℃; for 5h;
  • 21
  • [ 24767-82-6 ]
  • [ 71-43-2 ]
  • heptan-3-ylbenzene [ No CAS ]
  • [ 2132-84-5 ]
  • [ 1078-71-3 ]
  • [ 2132-86-7 ]
YieldReaction ConditionsOperation in experiment
at 85℃; for 5h;
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran at 25℃; reaction of cesium enolate of 2-p-biphenylylcyclohexanone with alkyl halides and sulfonates; relative reactivity of alkylating agents;
  • 23
  • [ 24767-82-6 ]
  • [ 98-88-4 ]
  • [ 1674-37-9 ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: 1-heptyl 4-methylbenzenesulfonate With manganese In tetrahydrofuran at 20℃; for 0.5h; Stage #2: benzoyl chloride In tetrahydrofuran; ethylene dibromide at 20℃; for 0.5h;
48% Stage #1: 1-heptyl 4-methylbenzenesulfonate With manganese In tetrahydrofuran at 20℃; for 0.333333h; Stage #2: benzoyl chloride In tetrahydrofuran at 20℃; for 0.5h;
  • 24
  • [ 24767-82-6 ]
  • [ 100-52-7 ]
  • [ 19396-73-7 ]
YieldReaction ConditionsOperation in experiment
64% Stage #1: 1-heptyl 4-methylbenzenesulfonate With manganese In tetrahydrofuran at 20℃; for 0.5h; Stage #2: benzaldehyde In tetrahydrofuran; ethylene dibromide at 20℃; for 0.5h;
64% Stage #1: 1-heptyl 4-methylbenzenesulfonate With manganese In tetrahydrofuran at 20℃; for 0.333333h; Stage #2: benzaldehyde In tetrahydrofuran at 20℃; for 0.5h;
  • 25
  • [ 24767-82-6 ]
  • [ 111-70-6 ]
YieldReaction ConditionsOperation in experiment
90% With cerium(III) chloride; sodium iodide In acetonitrile for 4h; Heating;
  • 26
  • [ 24767-82-6 ]
  • [ 15366-08-2 ]
  • [ 13151-34-3 ]
YieldReaction ConditionsOperation in experiment
71 % Chromat. With buta-1,3-diene In tetrahydrofuran at 20℃; for 3h;
With buta-1,3-diene; cobalt(II) chloride; lithium iodide In tetrahydrofuran at -78 - 50℃; for 5h; Inert atmosphere;
  • 27
  • [ 24767-82-6 ]
  • phenylmagnesium bromide [ No CAS ]
  • [ 142-82-5 ]
  • [ 1078-71-3 ]
YieldReaction ConditionsOperation in experiment
1: 85 % Chromat. 2: 3 % Chromat. With buta-1,3-diene In tetrahydrofuran at 25℃; for 3h;
  • 28
  • [ 24767-82-6 ]
  • [ 873-77-8 ]
  • [ 626234-66-0 ]
YieldReaction ConditionsOperation in experiment
96 % Chromat. With buta-1,3-diene In tetrahydrofuran at 20℃; for 3h;
  • 29
  • [ 24767-82-6 ]
  • [ 18146-00-4 ]
  • [ 872-05-9 ]
YieldReaction ConditionsOperation in experiment
78 % Chromat. With vinylmagnesium chloride In tetrahydrofuran at 25℃; for 3h;
  • 30
  • [ 24767-82-6 ]
  • [ 5824-40-8 ]
  • [ 7370-54-9 ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine In toluene for 10h; Heating;
  • 31
  • [ 24767-82-6 ]
  • [ 557-20-0 ]
  • [ 111-84-2 ]
YieldReaction ConditionsOperation in experiment
83 % Chromat. With 1-methyl-pyrrolidin-2-one; magnesium bromide; nickel dichloride In tetrahydrofuran; hexane at 25℃; for 1h;
  • 32
  • [ 24767-82-6 ]
  • [ 17334-08-6 ]
  • 2-heptyloxymethyl-1-methyl-1H-imidazole [ No CAS ]
  • 33
  • [ 24767-82-6 ]
  • [ 1078-71-3 ]
YieldReaction ConditionsOperation in experiment
90 % Chromat. With zinc(II) chloride In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 20℃; for 24h;
  • 34
  • [ 24767-82-6 ]
  • [ 693-04-9 ]
  • [ 1120-21-4 ]
YieldReaction ConditionsOperation in experiment
74 % Chromat. With 1-Phenylprop-1-yne; copper dichloride In tetrahydrofuran at 25℃; for 0.25h;
With buta-1,3-diene; nickel dibromide In tetrahydrofuran at 1℃; for 0.0416667h;
  • 35
  • [ 24767-82-6 ]
  • 4-Propoxy-cyclohexanecarboxylic acid 2,3-dicyano-4-heptyloxy-phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 5percent aq. NaOH / 1.) water, reflux, 7 h; 2.) toluene, reflux 2: pyridine
  • 36
  • [ 24767-82-6 ]
  • 4-Butoxy-cyclohexanecarboxylic acid 2,3-dicyano-4-heptyloxy-phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 5percent aq. NaOH / 1.) water, reflux, 7 h; 2.) toluene, reflux 2: pyridine
  • 37
  • [ 24767-82-6 ]
  • 4-Pentyloxy-cyclohexanecarboxylic acid 2,3-dicyano-4-heptyloxy-phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 5percent aq. NaOH / 1.) water, reflux, 7 h; 2.) toluene, reflux 2: pyridine
  • 38
  • [ 24767-82-6 ]
  • 4-Hexyloxy-cyclohexanecarboxylic acid 2,3-dicyano-4-heptyloxy-phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 5percent aq. NaOH / 1.) water, reflux, 7 h; 2.) toluene, reflux 2: pyridine
  • 39
  • [ 24767-82-6 ]
  • 4-(4-Propyl-cyclohexyl)-benzoic acid 2,3-dicyano-4-heptyloxy-phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 5percent aq. NaOH / 1.) water, reflux, 7 h; 2.) toluene, reflux 2: pyridine
  • 40
  • [ 24767-82-6 ]
  • 4-(4-Pentyl-cyclohexyl)-benzoic acid 2,3-dicyano-4-heptyloxy-phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 5percent aq. NaOH / 1.) water, reflux, 7 h; 2.) toluene, reflux 2: pyridine
  • 41
  • [ 24767-82-6 ]
  • 4-(4-Heptyl-cyclohexyl)-benzoic acid 2,3-dicyano-4-heptyloxy-phenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 5percent aq. NaOH / 1.) water, reflux, 7 h; 2.) toluene, reflux 2: pyridine
  • 42
  • [ 24767-82-6 ]
  • [ 110860-72-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 80 percent / sodium azide / dimethylformamide / 12 h / 80 °C 2: NaOEt / ethanol / 3 h / Heating
  • 43
  • [ 24767-82-6 ]
  • 3-Heptyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 80 percent / sodium azide / dimethylformamide / 12 h / 80 °C 2: NaOEt / ethanol / 3 h / Heating 3: 1 h / Heating 4: POCl3, N,N-diethylaniline / 1.5 h / 95 °C 5: 35percent aq. NH4OH / ethanol / 1.5 h / 80 °C
  • 44
  • [ 24767-82-6 ]
  • 7-Chloro-3-heptyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 80 percent / sodium azide / dimethylformamide / 12 h / 80 °C 2: NaOEt / ethanol / 3 h / Heating 3: 1 h / Heating 4: POCl3, N,N-diethylaniline / 1.5 h / 95 °C
  • 45
  • [ 24767-82-6 ]
  • [ 149355-87-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 80 percent / sodium azide / dimethylformamide / 12 h / 80 °C 2: NaOEt / ethanol / 3 h / Heating 3: 1 h / Heating
  • 46
  • [ 24767-82-6 ]
  • [ 149355-93-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 80 percent / sodium azide / dimethylformamide / 12 h / 80 °C 2: NaOEt / ethanol / 3 h / Heating 3: 70 percent / sodium ethoxide / 5 h / Heating 4: POCl3, N,N-diethylaniline / 1 h / 95 °C 5: 35percent aq. NH4OH / ethanol / 1 h / 80 °C
  • 47
  • [ 24767-82-6 ]
  • [ 149355-94-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 80 percent / sodium azide / dimethylformamide / 12 h / 80 °C 2: NaOEt / ethanol / 3 h / Heating 3: 70 percent / sodium ethoxide / 5 h / Heating
  • 48
  • [ 24767-82-6 ]
  • 7-Chloro-3-heptyl-5-phenyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 80 percent / sodium azide / dimethylformamide / 12 h / 80 °C 2: NaOEt / ethanol / 3 h / Heating 3: 70 percent / sodium ethoxide / 5 h / Heating 4: POCl3, N,N-diethylaniline / 1 h / 95 °C
  • 49
  • [ 24767-82-6 ]
  • [ 22987-10-6 ]
  • 3-propionylamino-N,N-di-n-heptylaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 2-methoxy-ethanol; water; sodium carbonate 4 EXAMPLE 4 STR13 EXAMPLE 4 STR13 3-Propionylaminoaniline (16.4 parts) was reacted with n-heptyl p-toluenesulfonate (64.8 parts) at 100° C. for 5 hours in a solvent comprising methyl cellosolve (100 parts) and water (100 parts) in the presence of anhydrous sodium carbonate (12.7 parts) to obtain 3-propionylamino-N,N-di-n-heptylaniline (coupling component).
  • 50
  • [ 24767-82-6 ]
  • [ 22987-10-6 ]
  • 3-propionylamino-N-heptylaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 2-methoxy-ethanol; sodium carbonate 7 EXAMPLE 7 STR16 EXAMPLE 7 STR16 3-Propionylaminoaniline (16.4 parts) was reacted with n-heptyl p-toluenesulfonate (27 parts) at 100° C. for 4 hours in methyl cellosolve (200 parts) in the presence of anhydrous sodium carbonate (5.3 parts) to obtain 3-propionylamino-N-heptylaniline.
  • 51
  • [ 24767-82-6 ]
  • [ 7439-96-5 ]
  • CH3(CH2)6MnOSO2C6H4CH3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran (Ar); addn. of Et(CH2)4CH2OTs in THF via cannula to stirred at room temp. slurry of highly active Mn in THF; stirring at room temp. for 20 min; monitoring by gas chromy.;
  • 52
  • [ 24767-82-6 ]
  • [ 101453-26-3 ]
YieldReaction ConditionsOperation in experiment
94% With carbon disulfide; caesium carbonate In dimethyl sulfoxide at 20 - 25℃; for 3h; Inert atmosphere;
  • 53
  • [ 24767-82-6 ]
  • [ 693-39-0 ]
YieldReaction ConditionsOperation in experiment
53% With tetrabutylammonium nitrite In toluene at 20℃; for 2.5h;
  • 54
  • [ 24767-82-6 ]
  • [ 347885-68-1 ]
  • [ 1282036-57-0 ]
YieldReaction ConditionsOperation in experiment
48% With nickel(II) iodide; 4,5-dihydro-2-(pyridin-2-yl)-1H-imidazole; lithium methanolate; bis(pinacol)diborane In 1-methyl-pyrrolidin-2-one at 40℃; for 16h;
  • 55
  • [ 24767-82-6 ]
  • [ 111-68-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium azide / N,N-dimethyl-formamide / 5 h / 80 °C / Inert atmosphere 2.1: triphenylphosphine / tetrahydrofuran / 22 h / 0 - 20 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere
  • 56
  • [ 24767-82-6 ]
  • C15H25NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium azide / N,N-dimethyl-formamide / 5 h / 80 °C / Inert atmosphere 2.1: triphenylphosphine / tetrahydrofuran / 22 h / 0 - 20 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere 3.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 15 h / 0 - 20 °C / Inert atmosphere
  • 57
  • [ 24767-82-6 ]
  • [ 1568923-81-8 ]
  • [ 1568923-78-3 ]
YieldReaction ConditionsOperation in experiment
160 mg With n-butyllithium; potassium carbonate In acetonitrile Reflux;
  • 58
  • [ 24767-82-6 ]
  • [ 108-01-0 ]
  • N-(2-hydroxyethyl)-N,N-dimethylheptane-1-aminium 4-methylbenzenesulphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In acetonitrile for 4h; Reflux; 4.2.2. General procedure for preparation of choline salts General procedure: A solution of alkyl 4-methylbenzenesulphonate (40 mmol) in acetonitrile (20 ml) was added to a solution of 2-(N,N-dimethylamino)ethanol (40 mmol) in acetonitrile (20 ml). The reaction mixture was refluxed for 4 h. The solvent was evaporated in vacuum and the crude solid was left for crystallisation from acetone yielding a white, hygroscopic solid as the product. The product was kept in vacuum desiccator over P4O10.
  • 59
  • [ 24767-82-6 ]
  • [ 629-59-4 ]
YieldReaction ConditionsOperation in experiment
80% With pyridine; manganese; trifluoroacetic acid; sodium iodide; cobalt(II) bromide In acetonitrile at 50℃;
  • 60
  • [ 24767-82-6 ]
  • [ 162360-77-2 ]
  • 2-amino-2-(4-(heptyloxy)phenethyl)propane-1,3-diol hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C / Schlenk technique; Inert atmosphere 2.1: lithium hydroxide / water; methanol / Reflux 2.2: 3 h / 20 °C
  • 61
  • [ 24767-82-6 ]
  • [ 162360-77-2 ]
  • [ 162358-42-1 ]
YieldReaction ConditionsOperation in experiment
84% With caesium carbonate In N,N-dimethyl-formamide at 20℃; Schlenk technique; Inert atmosphere;
  • 62
  • [ 24767-82-6 ]
  • [ 108-44-1 ]
  • N,N-diheptyl-m-methylaniline [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With tetrabutylammomium bromide; sodium hydroxide at 100℃; for 8h; 7 Taking paratoluene sulfonic acid heptyl esters 2.70 g (0.01 µM), at room temperature by adding 0.38 g (0.0036 µM)-toluidine, adding 0.05 g ammonium bromide [...] transfer catalyst, heating up to 100 °C dropwise 25% sodium hydroxide solution of 1.6 g (0.01 µM), maintaining the temperature reaction 8 h after, to room temperature, extracted with ethyl acetate, dried and filtered, rotary evaporation, can be dark purple viscous liquid, by silica gel column to obtain a pale yellow liquid 0.99 g, N, N - between the two heptyl-toluidine yield is 91%.
  • 63
  • [ 24767-82-6 ]
  • 2-(4-(8-((benzyloxy)amino)-8-oxooctanamido)phenyl)acetic acid [ No CAS ]
  • heptyl 2-(4-(8-((benzyloxy)amino)-8-oxooctanamido)phenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 16h; Schlenk technique;
  • 64
  • [ 24767-82-6 ]
  • heptyl 2-(4-(8-(hydroxyamino)-8-oxooctanamido)phenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 70 °C / Schlenk technique 2: boron trichloride / dichloromethane; tetrahydrofuran / 2.08 h / 0 - 20 °C / Schlenk technique
  • 65
  • [ 24767-82-6 ]
  • [ 118334-83-1 ]
  • (3s,5s,7s)-1-(heptylsulfonyl)adamantane [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With sodium dithionite; tetrabutylammomium bromide; N-ethyl-N,N-diisopropylamine; zinc(II) chloride In water; N,N-dimethyl-formamide; acetonitrile at 120℃; for 15h; Inert atmosphere; Schlenk technique;
68% With sodium dithionite; tetrabutylammomium bromide; N-ethyl-N,N-diisopropylamine; zinc(II) chloride In N,N-dimethyl acetamide; water; acetonitrile at 120℃; for 15h; Inert atmosphere; 37 Synthesis of compound 3ak: Add redox ester derived from adamantane formic acid (65.0 mg, 0.2 mmol) to the reaction tube,Sodium dithionite (69.6mg, 0.4mmol), n-heptyl p-toluenesulfonate (162.2mg, 0.6mmol), N,N’-diisopropylethylamine (51.7mg, 0.4mmol),Zinc chloride (13.6mg, 0.1mmol), tetrabutylammonium bromide (96.7mg, 0.3mmol),Water (60μL), DMF/CH3CN (2:1, 2mL), react at 120 for 15h under nitrogen protection,Point the board to monitor until the redox ester is consumed completely, move to room temperature, add water to quench,Extract with ethyl acetate and collect the organic phase. The organic phase is dried with anhydrous sodium sulfate,The solvent was removed under reduced pressure, and the product 3ak (40.6 mg) was obtained by column chromatography with a yield of 68%.
  • 66
  • [ 123-75-1 ]
  • [ 24767-82-6 ]
  • N,N-diheptylpyrrolidinium 4-methylbenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With potassium carbonate In water at 100℃; for 18h;
  • 67
  • [ 110-89-4 ]
  • [ 24767-82-6 ]
  • N,N-diheptylpiperidinium 4-methylbenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With potassium carbonate In water at 100℃; for 18h;
  • 68
  • [ 35152-38-6 ]
  • [ 24767-82-6 ]
  • N-heptyl-N-pentylpyrrolidinium 4-methylbenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% at 100℃; for 12h;
  • 69
  • [ 111-49-9 ]
  • [ 24767-82-6 ]
  • N,N-diheptylazepanium 4-methylbenzenesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With potassium carbonate In water at 100℃; for 18h;
  • 70
  • [ 24767-82-6 ]
  • [ 107-21-1 ]
  • [ 7409-44-1 ]
YieldReaction ConditionsOperation in experiment
95% With tetra-(n-butyl)ammonium iodide at 100℃; for 0.5h; 1.1.2-1.1.5 2. Add ethylene glycol (1.5L) directly to the above milky white solid,Phase transfer catalyst tetrabutylammonium iodide (74g, 0.2mol),Then move the reaction flask to a 100°C oil bath and continue to react for 30 minutes.Then the reaction solution was quickly mixed with 2.0 kg of crushed ice,After the crushed ice melts, add an appropriate amount of concentrated hydrochloric acid to the mixture to reach a pH of 7.Separate the organic phase. 3. Extract the aqueous phase twice with 500 mL ethyl acetate, combine the organic phases, wash the organic phase with 500 mL each of water and saturated brine, dry the organic phase over anhydrous sodium sulfate for half an hour, filter out the desiccant, and concentrate under reduced pressure to obtain a crude product. 4. After the crude product is distilled under reduced pressure, 2-heptyloxy-1-ethanol (152 g, yield 95%, purity 99.5%) is obtained. 5. Ethylene glycol recovery: the water phase is first heated and dehydrated under reduced pressure, filtered to remove solid salts, and then distilled under reduced pressure to obtain ethylene glycol. The recovered ethylene glycol can be directly used in the above-mentioned second step reaction.
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