[ CAS No. 14098-44-3 ] {[proInfo.proName]}

Name: 14098-44-3|Benzo-15-crown-5|98%
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3d Animation Molecule Structure of 14098-44-3

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Quality Control of [ 14098-44-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 14098-44-3 ]

Product Details of [ 14098-44-3 ]

CAS No. :	14098-44-3	MDL No. :	MFCD00005945
Formula :	C₁₄H₂₀O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FNEPSTUXZLEUCK-UHFFFAOYSA-N
M.W :	268.31	Pubchem ID :	84197
Synonyms :

Calculated chemistry of [ 14098-44-3 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.57
Num. rotatable bonds :	0
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	69.41
TPSA :	46.15 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.29 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.62
Log Po/w (XLOGP3) :	0.91
Log Po/w (WLOGP) :	1.51
Log Po/w (MLOGP) :	0.26
Log Po/w (SILICOS-IT) :	2.34
Consensus Log Po/w :	1.53

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.31
Solubility :	1.31 mg/ml ; 0.00489 mol/l
Class :	Soluble
Log S (Ali) :	-1.46
Solubility :	9.2 mg/ml ; 0.0343 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.33
Solubility :	0.127 mg/ml ; 0.000472 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.92

Safety of [ 14098-44-3 ]

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

Application In Synthesis of [ 14098-44-3 ]

* 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.

Upstream synthesis route of [ 14098-44-3 ]
Downstream synthetic route of [ 14098-44-3 ]

[ 14098-44-3 ] Synthesis Path-Upstream 1~1

1
[ 91-16-7 ]
[ 14098-44-3 ]
[ 808-57-1 ]
[ 139021-90-2 ]

Reference： [1] Tetrahedron Letters, 1991, vol. 32, # 50, p. 7405 - 7408

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Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;
	Multi-step reaction with 2 steps 1: 98 percent / aq. HNO₃; CH₃COOH / CHCl₃ 2: 100 percent / N₂H₄*nH₂O / Pd/C / dioxane
	Multi-step reaction with 2 steps 1: fuming nitric acid / CCl₄ / 3.5 h / 20 - 45 °C 2: 86 percent / hydrazine hydrate / 4 percent Pd/C / ethanol / 1.5 h / Heating

	Multi-step reaction with 2 steps 1: HNO₃ / acetic acid 2: H₂ / Pd/C
	Multi-step reaction with 2 steps 1: HNO₃ (d = 1.42, 70percent) / acetic acid / 0.5 h 2: 1.0 g / hydrogen / Raney Ni/H₂₀ slurry / dimethylformamide / 1.5 h / 2068.6 Torr
	Multi-step reaction with 2 steps 1: nitric acid; acetic acid 2: palladium on activated charcoal; hydrazine
	Multi-step reaction with 2 steps 1: nitric acid; acetic acid 2: hydrazine; platinum
	Multi-step reaction with 2 steps 1: acetic acid; nitric acid 2: palladium on activated charcoal
	Multi-step reaction with 2 steps 1: nitric acid / acetonitrile / 0.33 h / 70 °C 2: hydrazine hydrate / methanol / 1.75 h / 35 °C / Reflux
	Multi-step reaction with 2 steps 1: nitric acid; acetic acid / chloroform / 0 - 20 °C 2: palladium on activated charcoal; hydrazine hydrate / ethanol / 5 h / Reflux

Yield	Reaction Conditions	Operation in experiment
99.5%	With nitric acid; In acetonitrile;	Benzo-15-crown-5 nitration was carried outby nitric acid, 58%, over boiling reaction mass in theacetonitrile media, using relevant method17.Nitric acid of various concentrations can beused in nitration reaction. In some cases, diluted nitric acid (which is poor nitration agent and quite strongoxidizing agent) is also used due to the constantpresence of nitrous acid that hinders nitration.Another drawback of diluted nitric acid, which limitsits use, is its ability to express nitrating effect only athigh temperatures, which are featured by prevailingside oxidation reaction. Concentrated nitric acidshows nitrating effect at lower temperatures and lesslikely to cause undesirable oxidation, which is why wecarried out a nitration of resulted <strong>[14098-44-3]benzo-15-crown-5</strong>with nitric acid, 56%, in the acetonitrile media. Theyield of target product was 99.5%, while the meltingpoint of resulted compound was 94-95 0C.Infrared spectrum (KBr, nu, cm-1): 497(weak), 538 (weak), 618 (weak), 654 (medium)(aromatic C-H), 723 (weak), 745 (medium) (NO2),787 (weak), 806 (medium), 868 (medium) (N-O), 913(weak), 934 (medium), 980 (medium), 1010(weak),1047 (medium), 1093 (strong) (C-N), 1138 (strong)(C-O-C), 1240 (strong) (NO2), 1276 (strong) (NO2),1335 (strong) (NO2), 1417 (strong), 1428 (strong),1448 (medium) (N=O), 1517 (strong) (CH2 + NO2),1587 (medium) (aromatic C-C), 2868 (medium)(C-H), 2904 (medium) (C-H), 2929 (medium) (C-H),3083 (medium) (aromatic C-H).1H N u c l e a r m a g n e t i c r e s o n a n c e(DMSO-d6, 300 MHz): 3.62 (broad singlet, 8H,CH2+CH2+CH2+CH2), 3.74-3.85 (multiplet, 4H,CH2+CH2), 4.13-4.24 (multiplet, 4H, CH2+CH2), 7.15(doublet, 1H, J=8.9, CH), 7.73 (doublet, 1H, J=2.7,CH), 7.89 (double doublet, 1H, J=8.9, J=2.7, CH).13C Nuclear magnetic resonance (DMSO-d6,75 MHz): 67.77, 68.84, 69.27, 69.71, 70.09, 70.16,70.30, 100.96, 105.53, 117.49, 139.35, 143.95,149.92.
89%	With tert.-butylnitrite; In acetonitrile; at 20℃; for 24h;	1 mmol of <strong>[14098-44-3]benzo-15-crown-5</strong> was added to the reaction flask, dissolved in 2 mL of acetonitrile, and 145 uL of t-butyl nitrite was added. The mixture was stirred at room temperature for 24 hours. After the reaction was completed, the organic solvent was removed by a rotary evaporator. Solvent, column chromatography gave the product nitro product, the reaction yield was 89%
72%	With nitric acid; In acetonitrile; at 70℃; for 0.333333h;	A solution of 26.8 g(0.10 mol) of <strong>[14098-44-3]benzo-15-crown-5</strong> in 14 mL ofacetonitrile was heated to 70C, 12 mL (0.15 mol) of58% nitric acid was added dropwise, and the mixturewas stirred for 20 min, cooled to room temperature,and diluted with 120 mL of cold water. The lightyellow crystalline solid was filtered off, recrystallizedfrom propan-2-ol, and dried in air. Yield 72%, mp 95-96C, purity 97% (GC/MS). IR spectrum, nu, cm-1: 497w, 538 w, 618 w, 654 m, 723 w, 745 m, 787 w, 806 m,868 m, 913 w, 934 m, 980 m, 1010 w, 1047 m, 1093 s,1138 s, 1240 s, 1276 s, 1335 s, 1417 s, 1428 s, 1448 m,1517 s, 1587 m, 2868 m, 2904 m, 2929 m, 3083 m. 1HNMR spectrum, delta, ppm: 3.62 br.s (8H), 3.74-3.85 m(4H), 4.13-4.24 m (4H), 7.15 d (1H, J = 8.9), 7.73 d(1H, J = 2.7 Hz), 7.89 d (1H, J = 8.9 Hz). 13C NMRspectrum, deltaC, ppm: 70.09, 70.16, 70.30, 100.96,105.53, 117.49, 139.35, 143.95, 149.92. Found, %: C54.01; H 6.23 N 4.27. C14H19NO7. Calculated, %: C53.62; H 6.06; N 4.47.

Yield	Reaction Conditions	Operation in experiment
78%	With trifluoroacetic acid; at 90℃; for 15h;Inert atmosphere;	The mixture of <strong>[14098-44-3]benzo-15-crown-5</strong> (2.016 g, 5.6 mmol), hexamethylene tetraamine (3.22 g, 22 mmol) in trifluoracetic acid (8 mL) was stirred in a 25 ml round bottomed flask at 90 C under nitrogen atmosphere for 15 hrs., cooled and then extracted in 25 ml benzene and dried using magnesium sulphate. Concentration of the benzene extract under vacuum gave a brown oil, which solidified on cooling as white crystalline solid to furnish desired compd. 1. M.P. 76-78 C, Yield, 1.75 g; 78%).
75%	With trifluoroacetic acid; at 90℃; for 24h;Inert atmosphere;	A mixture of benzo-crown-5 (1a, 4.29 g, 16 mmol), hexamethylenetetramine (HMTA) (2.24 g, 16 mmol) and trifluoroacetic acid (TFA) (11.2 ml) was stirred at 90 C for 24 h under argon atmosphere. The resulting brown solution was poured into crushed ice and subsequently extracted with dichloromethane. The organic layer was washed with water, brine and dried (Na2SO4). Evaporation of the solvent yielded a brown mass which was purified by column chromatography on silica using CHCl3-MeOH (98:2) as eluant to afford pure 1b (3.56 g, 75%). 4'-Formyl<strong>[14098-44-3]benzo-15-crown-5</strong> (1b): white solid; mp 78-79 C; IR (CHCl3): upsilon 3017, 2929, 2873, 2733, 1685, 1596, 1586, 1509, 1453, 1437, 1273, 1215, 1136, 1051 cm- 1; 1H NMR (200 MHz, CDCl3): delta 3.75 (s, 8H), 3.89-3.95 (m, 4H), 4.16-4.22 (m, 4H), 6.93 (d, J = 8.1 Hz, 1H), 7.37 (d, J = 1.7 Hz, 1H), 7.43 (dd, J = 8.1, 1.7 Hz, 1H); 13C NMR (50 MHz, CDCl3): delta 68.6, 68.8, 69.0, 69.1, 70.1, 70.2, 71.0, 111.5, 112.1, 126.5, 130.1, 149.3, 154.5, 190.5.

[ CAS No. 14098-44-3 ] {[proInfo.proName]}

Quality Control of [ 14098-44-3 ]

Related Doc. of [ 14098-44-3 ]

Product Details of [ 14098-44-3 ]

Calculated chemistry of [ 14098-44-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 14098-44-3 ]

Application In Synthesis of [ 14098-44-3 ]

[ 14098-44-3 ] Synthesis Path-Upstream 1~1

[ 14098-44-3 ] Synthesis Path-Downstream 1~59

Precautionary Statements-General

Prevention

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Yield	Reaction Conditions	Operation in experiment
92%	With sodium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane
61%	With sodium hydroxide; tetra-(n-butyl)ammonium iodide; p-toluenesulfonyl chloride In toluene at 70 - 75℃; for 13h;

Yield	Reaction Conditions	Operation in experiment
80%	With PPA In acetic acid at 60℃;
70%	With PPA; methanesulfonic acid; phosphorus pentoxide In acetic acid
57%	In dichloromethane at 83℃;

Yield	Reaction Conditions	Operation in experiment
82.097%		General procedure 88 g (0.8 mole) catechol and 1200 mln-butanol was plased into a 2-liter ask equippedwith a mechanical stirrer, thermometer, watercondenser and dropping funnel was placed. Afterdissolution of the catechol by stirring, aqueous NaOHsolution (67.2 g NaOH to 80 ml H2O) was added.Mixing duration was 30 to 40 minutes. After 156.6 ml(0.8 mole) tetraethyleneglycol dichloride wasdripped through dropping funnel at 17 ml/min rate.The mixture was reuxed for 7 hours (107 0C). Afterthat, the fltrate was acidifed with concentratedhydrochloric acid, fltered off and ushed with wateruntil neutral reaction was reached. Upper organiclayer was put into round-bottom ask, treated withactivated carbon and fltered off. Then the fltrate wasboiled out using rotary evaporator, accompaniedby complete solvent distillation. The residue wasextracted with hexane, followed by producing whitetransparent crystals of benzo-15-crown-5
60%		A mixture of (30 mmol) of catechol, 50 ml of 1-butanol and (60 mmol) of sodium hydroxide dissolved in 10 ml of water was stirred for 5 min under nitrogen and treated with (30 mmol) of 1, 11-dichloro-3, 6, 9-trioxaundecane. The mixture was refluxed with good agitation for 30 h during which the temperature dropped from102 to 100 C. The mixture was acidified with concentrated hydrochloric acid, cooled to RT, filtered, and the resultant solids were washed with 30 ml of methanol.The filtrate and the washings were combined and evaporated to dryness in a rotary vacuum evaporator. The residue was recrystallized in n-heptane to obtained benzo15-crown-5 (yield = 60 %).
47%	With sodium hydroxide; In water; butan-1-ol; at 60 - 65℃; for 5h;	A solution of 67.2 g (1.68 mol)of sodium hydroxide in 80 mL of water was added to asolution of 88.0 g (0.80 mol) of catechol in 1200 mL ofbutan-1-ol heated to 60-65C. Tetraethylene glycoldichloride, 194.8 g (0.84 mol), was then added dropwise,and the mixture was heated for 5 h and filtered. Thefiltrate was acidified with 12 mL of concentratedaqueous HCl, and the organic phase was separated,washed with water until neutral reaction, and evaporatedto dryness at 48-58C (30-40). The residue wasextracted with hot hexane, the extract was cooled, andthe precipitate was filtered off. Yield 47%, colorlesstransparent crystals, mp 78-79C, purity 98% (GC/MS). IR spectrum, nu, cm-1: 468 w, 514 w, 538 w, 602w, 740 s, 779 w, 851 m, 906 w, 938 s, 980 w, 1042 m,1051 s, 1076 m, 1094 m, 1121 s, 1130 s, 1226 s, 1261s, 1269 m, 1335 m, 1345 m, 1362 w, 1412 w, 1455 m,1509 s, 1593 m, 2863 s, 2920 s, 2940 s, 3009 w, 3036w, 3060 w. 1H NMR spectrum, delta, ppm: 3.62 br.s (8H),3.73-3.81 m (4H), 4.00-4.09 m (4H), 6.85-6.99 m(4H). 13C NMR spectrum, deltaC, ppm: 68.42, 68.87, 69.79,70.42, 113.92, 121.04, 148.63. Found, %: C 62.79; H7.43. C14H22O5. Calculated, %: C 62.61; H 7.62.

Yield	Reaction Conditions	Operation in experiment
58%	With sodium hydroxide; tetra-(n-butyl)ammonium iodide In toluene for 16h; Heating;
52%	Stage #1: benzene-1,2-diol With sodium hydroxide; tetra-(n-butyl)ammonium iodide In water; toluene at 50 - 60℃; for 0.5h; Stage #2: tetraethylene glycol di(p-toluenesulfonate) In water; toluene for 16h; Reflux;
40%	With sodium hydroxide In tetrahydrofuran

Yield	Reaction Conditions	Operation in experiment
90.1%	With tetramethyl ammoniumhydroxide In water; dimethyl sulfoxide at 25℃;
90.1 % Spectr.	With tetramethyl ammoniumhydroxide In water; dimethyl sulfoxide at 25℃;

Yield	Reaction Conditions	Operation in experiment
96%	With PPA at 70℃; for 5h;
95%	With PPA at 60℃; for 5h;
94%	With sulfuric acid In chloroform Heating;

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: N-methyl-N-phenylformamide With trichlorophosphate In neat (no solvent) for 0.25h; Stage #2: 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin In neat (no solvent) at 75℃; for 3h;
40%	With trichlorophosphate
26%

Yield	Reaction Conditions	Operation in experiment
68%	With sulfuric acid; iodine; periodic acid In water; acetic acid at 70℃; for 16h;
64%	With N-iodo-succinimide In water at 20℃; for 2h;

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 51 percent / bromine / iodine / acetic acid 2: 31 percent / dimethylformamide / 5 h / Heating
	Multi-step reaction with 2 steps 1: 70 percent / bromine / acetic acid / 28 h / Ambient temperature 2: 66 percent / dimethylformamide / 160 - 170 °C / Heating
	Multi-step reaction with 2 steps 1: N-Bromosuccinimide / chloroform / 4 h / Reflux 2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,1'-bis-(diphenylphosphino)ferrocene; 1,3-dimethylamylamine / 2.5 h / 120 °C / Inert atmosphere

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 51 percent / bromine / iodine / acetic acid 2: 31 percent / dimethylformamide / 5 h / Heating 3: 38 percent / ammonia, 2-(dimethylamino)ethanol / 17 h / Heating
	Multi-step reaction with 3 steps 1: 70 percent / bromine / acetic acid / 28 h / Ambient temperature 2: 66 percent / dimethylformamide / 160 - 170 °C / Heating 3: 32.16 percent / hydroquinone / 16 h / 180 °C / Heating

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